diff --git a/frontend/bun.lockb b/frontend/bun.lockb
index 21fea5d1..98c57341 100755
Binary files a/frontend/bun.lockb and b/frontend/bun.lockb differ
diff --git a/frontend/src/StateProvider.tsx b/frontend/src/StateProvider.tsx
new file mode 100644
index 00000000..6bb45dfa
--- /dev/null
+++ b/frontend/src/StateProvider.tsx
@@ -0,0 +1,89 @@
+import React, { createContext, useState } from "react"
+import { useToast } from "./hooks/use-toast"
+import { isSupportedFileType } from "./lib/common"
+
+// Define the context and its type
+export const StateContext = createContext<{
+  stagedFiles: File[]
+  setStagedFiles: React.Dispatch<React.SetStateAction<File[]>>
+  handleFileRemove: (index: number) => void
+  handleFileSelection: (event: React.ChangeEvent<HTMLInputElement>) => void
+  loading: boolean
+  setLoading: React.Dispatch<React.SetStateAction<boolean>>
+  query: string
+  setQuery: React.Dispatch<React.SetStateAction<string>>
+} | null>(null)
+
+// Provider component
+export const StateContextProvider: React.FC<{ children: React.ReactNode }> = ({
+  children,
+}) => {
+  const [stagedFiles, setStagedFiles] = useState<File[]>([])
+  const [loading, setLoading] = useState<boolean>(false)
+  const [query, setQuery] = useState<string>("")
+  const { toast } = useToast()
+
+  const handleFileSelection = (event: React.ChangeEvent<HTMLInputElement>) => {
+    const files = event?.target?.files
+    const validFiles: File[] = [] // Array to hold files that pass validation
+
+    if (files) {
+      Array.from(files).forEach((file) => {
+        // File size check: 20 MB limit
+        const fileSizeInMB = file.size / (1024 * 1024)
+        if (fileSizeInMB > 20) {
+          toast({
+            title: `File Too Large`,
+            description: `The file "${file.name}" exceeds the 20MB size limit. Please choose a smaller file.`,
+            variant: "destructive",
+          })
+        } else if (!isSupportedFileType(file.type)) {
+          // Check for unsupported file types
+          toast({
+            title: "File Type not supported",
+            description: `The file "${file.name}" is of type "${file.type}", which is not supported. Please upload a valid file type.`,
+            variant: "destructive",
+          })
+        } else {
+          // If valid, add the file to the validFiles array
+          validFiles.push(file)
+        }
+      })
+    }
+
+    setStagedFiles((prev) => {
+      if (prev.length + validFiles.length > 5) {
+        toast({
+          title: "File Limit Exceeded",
+          description: "You can only select up to 5 files.",
+          variant: "destructive",
+        })
+        return prev // Keep the current files unchanged
+      }
+      return [...prev, ...validFiles]
+    })
+
+    event.target.value = ""
+  }
+
+  function handleFileRemove(index: number) {
+    setStagedFiles((prev) => prev.filter((_, i) => i !== index))
+  }
+
+  return (
+    <StateContext.Provider
+      value={{
+        stagedFiles,
+        setStagedFiles,
+        handleFileRemove,
+        handleFileSelection,
+        loading,
+        setLoading,
+        query,
+        setQuery,
+      }}
+    >
+      {children}
+    </StateContext.Provider>
+  )
+}
diff --git a/frontend/src/components/ChatBox.tsx b/frontend/src/components/ChatBox.tsx
index ffe35d45..8ba9aaa4 100644
--- a/frontend/src/components/ChatBox.tsx
+++ b/frontend/src/components/ChatBox.tsx
@@ -1,20 +1,44 @@
-import { ArrowRight, Globe, Paperclip } from "lucide-react"
+import {
+  ArrowRight,
+  LoaderCircle,
+  File,
+  Trash2,
+  Globe,
+  Paperclip,
+} from "lucide-react"
 import { useEffect, useRef } from "react"
 
 interface ChatBoxProps {
   query: string
   setQuery: (query: string) => void
   handleSend: (messageToSend: string) => void
+  stagedFiles: File[]
+  handleFileRemove: (index: number) => void
+  handleFileSelection: (event: React.ChangeEvent<HTMLInputElement>) => void
+  loading: boolean
   isStreaming?: boolean
 }
 
+export const getFileTypeName = (fileType: string): string => {
+  if (fileType === "application/pdf") {
+    return "PDF"
+  } else {
+    return ""
+  }
+}
+
 export const ChatBox = ({
   query,
   setQuery,
   handleSend,
+  stagedFiles,
+  handleFileRemove,
+  handleFileSelection,
+  loading,
   isStreaming = false,
 }: ChatBoxProps) => {
   const inputRef = useRef<HTMLTextAreaElement | null>(null)
+  const fileInputRef = useRef<HTMLInputElement>(null)
   useEffect(() => {
     if (inputRef.current) {
       inputRef.current.focus()
@@ -26,26 +50,63 @@ export const ChatBox = ({
   }, [])
   return (
     <div className="flex flex-col w-full border rounded-[20px] sticky bottom-[20px] bg-white">
-      <div className="relative flex items-center">
-        <textarea
-          ref={inputRef}
-          rows={1}
-          placeholder="Ask anything across apps..."
-          value={query}
-          className="flex-grow resize-none bg-transparent outline-none text-[15px] font-[450] leading-[24px] text-[#1C1D1F] placeholder-[#ACBCCC] pl-[16px] pt-[14px] max-h-[108px] overflow-auto"
-          onChange={(e) => setQuery(e.target.value)}
-          onKeyDown={(e) => {
-            if (e.key === "Enter" && !e.shiftKey) {
-              e.preventDefault()
-              handleSend(query)
-            }
-          }}
-          style={{
-            height: "auto",
-            minHeight: "40px",
-            maxHeight: "108px",
-          }}
-        />
+      <div className="relative flex-col items-center">
+        {stagedFiles?.length > 0 && (
+          <div className="flex w-full">
+            <ul className="flex overflow-x-auto space-x-4 p-2">
+              {stagedFiles.map((file, index) => (
+                <li
+                  key={index}
+                  className="flex items-center p-2 border rounded border-gray-300 min-w-[200px] max-w-[200px]"
+                >
+                  <div className="flex items-center justify-center w-8 h-8 mr-2 bg-gray-100 rounded">
+                    <File className="text-black" size={16} />
+                  </div>
+                  <div className="flex flex-col">
+                    <span className="text-sm font-medium text-gray-700 truncate max-w-[100px]">
+                      {file.name}
+                    </span>
+                    <span className="text-xs font-medium text-gray-700 truncate max-w-[100px]">
+                      {getFileTypeName(file.type) ?? null}
+                    </span>
+                  </div>
+                  <button
+                    className="ml-auto text-sm"
+                    onClick={() => handleFileRemove(index)}
+                  >
+                    <Trash2
+                      className="text-red-500 hover:text-red-700"
+                      size={16}
+                    />
+                  </button>
+                </li>
+              ))}
+            </ul>
+          </div>
+        )}
+        <div className="flex">
+          <textarea
+            ref={inputRef}
+            rows={1}
+            placeholder="Ask anything across apps..."
+            value={query}
+            className="flex-grow resize-none bg-transparent outline-none text-[15px] font-[450] leading-[24px] text-[#1C1D1F] placeholder-[#ACBCCC] pl-[16px] pt-[14px] max-h-[108px] overflow-auto"
+            onChange={(e) => setQuery(e.target.value)}
+            onKeyDown={(e) => {
+              if (e.key === "Enter" && !e.shiftKey) {
+                e.preventDefault()
+                if (!isStreaming) {
+                  handleSend(query)
+                }
+              }
+            }}
+            style={{
+              height: "auto",
+              minHeight: "40px",
+              maxHeight: "108px",
+            }}
+          />
+        </div>
       </div>
       <div
         className="flex ml-[16px] mr-[6px] mb-[6px] items-center space-x-3 pt-2 cursor-text"
@@ -53,16 +114,35 @@ export const ChatBox = ({
           inputRef?.current?.focus()
         }}
       >
-        <Paperclip size={16} className="text-[#464D53] cursor-pointer" />
-        <Globe size={16} className="text-[#464D53] cursor-pointer" />
-        <button
-          disabled={isStreaming}
-          onClick={() => handleSend(query)}
-          style={{ marginLeft: "auto" }}
-          className={`flex mr-6 bg-[#464B53] text-white ${!isStreaming ? "hover:bg-[#5a5f66]" : ""}  rounded-full w-[32px] h-[32px] items-center justify-center disabled:opacity-50`}
-        >
-          <ArrowRight className="text-white" size={16} />
+        <button onClick={() => fileInputRef.current!.click()}>
+          <Paperclip size={16} className="text-[#464D53] cursor-pointer" />
         </button>
+        <input
+          type="file"
+          ref={fileInputRef}
+          style={{ display: "none" }}
+          onChange={handleFileSelection}
+          multiple
+        />
+
+        <Globe size={16} className="text-[#464D53] cursor-pointer" />
+        {loading ? (
+          <span
+            style={{ marginLeft: "auto" }}
+            className="flex mr-6 bg-[#464B53] text-white hover:bg-[#5a5f66] rounded-full w-[32px] h-[32px] items-center justify-center"
+          >
+            <LoaderCircle className="text-white animate-spin" size={16} />
+          </span>
+        ) : (
+          <button
+            disabled={isStreaming}
+            onClick={() => handleSend(query)}
+            style={{ marginLeft: "auto" }}
+            className={`flex mr-6 bg-[#464B53] text-white ${!isStreaming ? "hover:bg-[#5a5f66]" : ""}  rounded-full w-[32px] h-[32px] items-center justify-center disabled:opacity-50`}
+          >
+            <ArrowRight className="text-white" size={16} />
+          </button>
+        )}
       </div>
     </div>
   )
diff --git a/frontend/src/components/GroupFilter.tsx b/frontend/src/components/GroupFilter.tsx
index 8b4172d5..5517b9f5 100644
--- a/frontend/src/components/GroupFilter.tsx
+++ b/frontend/src/components/GroupFilter.tsx
@@ -58,7 +58,11 @@ const GroupFilterItem = ({
   )
 }
 
-export const getName = (app: Apps, entity: Entity): string => {
+export const getName = (
+  app: Apps,
+  entity: Entity,
+  isChatAttachment?: boolean,
+): string => {
   if (app === Apps.Gmail) {
     if (isMailAttachment(entity)) {
       return "Attachments"
@@ -88,10 +92,12 @@ export const getName = (app: Apps, entity: Entity): string => {
     } else {
       return "Drive"
     }
-  } else if (app == Apps.GoogleWorkspace) {
+  } else if (app === Apps.GoogleWorkspace) {
     return "People"
-  } else if (app == Apps.GoogleCalendar && entity === CalendarEntity.Event) {
+  } else if (app === Apps.GoogleCalendar && entity === CalendarEntity.Event) {
     return "Event"
+  } else if (!app && !entity && isChatAttachment) {
+    return "Attachment"
   } else {
     throw new Error(`Invalid app ${app} and entity ${entity}`)
   }
diff --git a/frontend/src/hooks/use-toast.ts b/frontend/src/hooks/use-toast.ts
index 87206c27..afa4ba25 100644
--- a/frontend/src/hooks/use-toast.ts
+++ b/frontend/src/hooks/use-toast.ts
@@ -2,7 +2,7 @@ import * as React from "react"
 
 import type { ToastActionElement, ToastProps } from "@/components/ui/toast"
 
-const TOAST_LIMIT = 1
+const TOAST_LIMIT = 5
 const TOAST_REMOVE_DELAY = 1000000
 
 type ToasterToast = ToastProps & {
diff --git a/frontend/src/lib/common.tsx b/frontend/src/lib/common.tsx
index e6b3401d..388bef29 100644
--- a/frontend/src/lib/common.tsx
+++ b/frontend/src/lib/common.tsx
@@ -19,11 +19,14 @@ import {
   CalendarEntity,
   isMailAttachment,
 } from "shared/types"
+import { useContext } from "react"
+import { StateContext } from "@/StateProvider"
 
 export const getIcon = (
   app: Apps,
   entity: Entity,
   size?: { w: number; h: number; mr: number; ml?: number },
+  isChatAttachment?: boolean,
 ) => {
   let classNameVal = ""
   if (size) {
@@ -80,7 +83,27 @@ export const getIcon = (
     if (entity === CalendarEntity.Event) {
       return <img className={classNameVal} src={GoogleCalendarSvg} />
     }
+  } else if (!app && !entity && isChatAttachment) {
+    return <Paperclip size={12} className="text-[#464D53]" />
   } else {
     throw new Error(`Invalid app ${app} and entity ${entity}`)
   }
 }
+
+export const useStateContext = () => {
+  const context = useContext(StateContext)
+  if (!context) {
+    throw new Error(
+      "useStateContext must be used within a StateContextProvider",
+    )
+  }
+  return context
+}
+
+export const isSupportedFileType = (fileType: string): boolean => {
+  if (fileType === "application/pdf") {
+    return true
+  } else {
+    return false
+  }
+}
diff --git a/frontend/src/main.tsx b/frontend/src/main.tsx
index 0a9ba72c..ea538075 100644
--- a/frontend/src/main.tsx
+++ b/frontend/src/main.tsx
@@ -10,6 +10,7 @@ import { routeTree } from "@/routeTree.gen"
 import { Toaster } from "@/components/ui/toaster"
 
 import { QueryClient, QueryClientProvider } from "@tanstack/react-query"
+import { StateContextProvider } from "./StateProvider"
 
 const queryClient = new QueryClient({})
 
@@ -33,8 +34,10 @@ if (!rootElement.innerHTML) {
   root.render(
     <StrictMode>
       <QueryClientProvider client={queryClient}>
-        <RouterProvider router={router} />
-        <Toaster />
+        <StateContextProvider>
+          <RouterProvider router={router} />
+          <Toaster />
+        </StateContextProvider>
       </QueryClientProvider>
     </StrictMode>,
   )
diff --git a/frontend/src/routes/_authenticated/chat.tsx b/frontend/src/routes/_authenticated/chat.tsx
index c9c57055..794228ba 100644
--- a/frontend/src/routes/_authenticated/chat.tsx
+++ b/frontend/src/routes/_authenticated/chat.tsx
@@ -8,15 +8,28 @@ import {
   useRouterState,
   useSearch,
 } from "@tanstack/react-router"
-import { Bookmark, Copy, Ellipsis, Eye, EyeOff, Pencil } from "lucide-react"
+import {
+  Bookmark,
+  Copy,
+  Ellipsis,
+  Eye,
+  EyeOff,
+  Pencil,
+  File,
+} from "lucide-react"
 import { useEffect, useRef, useState } from "react"
-import { ChatSSEvents, SelectPublicMessage, Citation } from "shared/types"
+import {
+  ChatSSEvents,
+  SelectPublicMessage,
+  Citation,
+  AttachmentMetadata,
+} from "shared/types"
 import AssistantLogo from "@/assets/assistant-logo.svg"
 import Retry from "@/assets/retry.svg"
 import { PublicUser, PublicWorkspace } from "shared/types"
-import { ChatBox } from "@/components/ChatBox"
+import { ChatBox, getFileTypeName } from "@/components/ChatBox"
 import { z } from "zod"
-import { getIcon } from "@/lib/common"
+import { getIcon, useStateContext } from "@/lib/common"
 import { getName } from "@/components/GroupFilter"
 import {
   useQueryClient,
@@ -67,7 +80,6 @@ export const ChatPage = ({ user, workspace }: ChatPageProps) => {
 
   const hasHandledQueryParam = useRef(false)
 
-  const [query, setQuery] = useState("")
   const [messages, setMessages] = useState<SelectPublicMessage[]>(
     isWithChatId ? data?.messages || [] : [],
   )
@@ -147,6 +159,16 @@ export const ChatPage = ({ user, workspace }: ChatPageProps) => {
       console.error("Failed to rename chat:", error)
     },
   })
+  const {
+    stagedFiles,
+    setStagedFiles,
+    handleFileRemove,
+    handleFileSelection,
+    loading,
+    setLoading,
+    query,
+    setQuery,
+  } = useStateContext()
 
   useEffect(() => {
     if (inputRef.current) {
@@ -221,7 +243,6 @@ export const ChatPage = ({ user, workspace }: ChatPageProps) => {
       currentRespRef.current = null
     }
     inputRef.current?.focus()
-    setQuery("")
   }, [
     data?.chat?.isBookmarked,
     data?.chat?.title,
@@ -248,11 +269,24 @@ export const ChatPage = ({ user, workspace }: ChatPageProps) => {
     // Prevent the user from sending a query if streaming is already in progress.
     if (isStreaming) return
 
+    let uploadedFilesMetadata = []
+
+    if (stagedFiles.length !== 0) {
+      setLoading(true)
+      uploadedFilesMetadata = await handleFileUpload()
+      setStagedFiles([])
+      setLoading(false)
+    }
+
     setQuery("")
     // Append the user's message to the chat
     setMessages((prevMessages) => [
       ...prevMessages,
-      { messageRole: "user", message: messageToSend },
+      {
+        messageRole: "user",
+        message: messageToSend,
+        attachments: uploadedFilesMetadata,
+      },
     ])
 
     setIsStreaming(true)
@@ -265,6 +299,10 @@ export const ChatPage = ({ user, workspace }: ChatPageProps) => {
     }
     url.searchParams.append("modelId", "gpt-4o-mini")
     url.searchParams.append("message", encodeURIComponent(messageToSend))
+    url.searchParams.append(
+      "attachments",
+      JSON.stringify(uploadedFilesMetadata),
+    )
 
     const eventSource = new EventSource(url.toString(), {
       withCredentials: true,
@@ -762,6 +800,40 @@ export const ChatPage = ({ user, workspace }: ChatPageProps) => {
     setIsEditing(false)
   }
 
+  const handleFileUpload = async () => {
+    const formData = new FormData()
+    // Append each file to the FormData object
+    stagedFiles.forEach((file) => {
+      formData.append("files", file)
+    })
+
+    try {
+      // Making POST req like this is giving errors at the server side
+      // const response = await api.chat.upload.$post({
+      //   body: formData,
+      //   headers: {
+      //     "Content-Type": "multipart/form-data",
+      //   },
+      // })
+
+      // For now using simple fetch which works fine
+      const response = await fetch("/api/v1/chat/upload", {
+        method: "POST",
+        body: formData,
+      })
+
+      const result = await response.json()
+      if (response.ok) {
+        return result.attachmentsMetadata
+      } else {
+        console.error("File upload failed:")
+      }
+    } catch (error) {
+      console.error("Error uploading files:", error)
+      throw error
+    }
+  }
+
   return (
     <div className="h-full w-full flex flex-row bg-white">
       <Sidebar photoLink={user.photoLink ?? ""} role={user?.role} />
@@ -822,6 +894,7 @@ export const ChatPage = ({ user, workspace }: ChatPageProps) => {
                     <ChatMessage
                       key={index}
                       message={message.message}
+                      attachments={message.attachments}
                       isUser={message.messageRole === "user"}
                       responseDone={true}
                       citations={message?.sources?.map((c: Citation) => c.url)}
@@ -849,6 +922,7 @@ export const ChatPage = ({ user, workspace }: ChatPageProps) => {
                     {userMessageWithErr && (
                       <ChatMessage
                         message={message.errorMessage}
+                        attachments={message.attachments}
                         isUser={false}
                         responseDone={true}
                         citations={message?.sources?.map(
@@ -915,6 +989,10 @@ export const ChatPage = ({ user, workspace }: ChatPageProps) => {
               query={query}
               setQuery={setQuery}
               handleSend={handleSend}
+              stagedFiles={stagedFiles}
+              handleFileRemove={handleFileRemove}
+              handleFileSelection={handleFileSelection}
+              loading={loading}
               isStreaming={isStreaming}
             />
           </div>
@@ -964,9 +1042,18 @@ const Sources = ({
                   <div className="flex flex-col  mr-[12px] truncate">
                     <span className="truncate">{citation.title}</span>
                     <div className="flex items-center pb-[12px]">
-                      {getIcon(citation.app, citation.entity)}
+                      {citation?.sddocname === "chatAttachment"
+                        ? getIcon(
+                            citation.app,
+                            citation.entity,
+                            undefined,
+                            true,
+                          )
+                        : getIcon(citation.app, citation.entity)}
                       <span className="text-[#848DA1]">
-                        {getName(citation.app, citation.entity)}
+                        {citation?.sddocname === "chatAttachment"
+                          ? getName(citation.app, citation.entity, true)
+                          : getName(citation.app, citation.entity)}
                       </span>
                     </div>
                   </div>
@@ -984,6 +1071,7 @@ export const textToCitationIndex = /\[(\d+)\]/g
 
 const ChatMessage = ({
   message,
+  attachments,
   isUser,
   responseDone,
   isRetrying,
@@ -997,6 +1085,7 @@ const ChatMessage = ({
   isStreaming = false,
 }: {
   message: string
+  attachments?: AttachmentMetadata[]
   isUser: boolean
   responseDone: boolean
   isRetrying?: boolean
@@ -1035,7 +1124,33 @@ const ChatMessage = ({
       className={`${isUser ? "max-w-[75%]" : ""} rounded-[16px] ${isUser ? "bg-[#F0F2F4] text-[#1C1D1F] text-[15px] leading-[25px] self-end pt-[14px] pb-[14px] pl-[20px] pr-[20px]" : "text-[#1C1D1F] text-[15px] leading-[25px] self-start"}`}
     >
       {isUser ? (
-        message
+        <>
+          {attachments && attachments?.length > 0 && (
+            <div className="flex-col w-full">
+              <ul className="flex flex-col space-y-2 pb-2">
+                {attachments?.map((attachment, index) => (
+                  <li
+                    key={index}
+                    className="flex items-center p-2 border rounded border-gray-300 min-w-[200px] max-w-[300px]"
+                  >
+                    <div className="flex items-center justify-center w-8 h-8 mr-2 bg-gray-100 rounded">
+                      <File className="text-black" size={16} />
+                    </div>
+                    <div className="flex flex-col flex-1">
+                      <span className="text-sm font-medium text-gray-700 truncate max-w-[100px]">
+                        {attachment?.fileName}
+                      </span>
+                      <span className="text-xs font-medium text-gray-700 truncate max-w-[100px]">
+                        {getFileTypeName(attachment?.fileType) ?? null}
+                      </span>
+                    </div>
+                  </li>
+                ))}
+              </ul>
+            </div>
+          )}
+          {message}
+        </>
       ) : (
         <div
           className={`flex flex-col mt-[40px] ${citations.length ? "mb-[35px]" : ""}`}
diff --git a/frontend/src/routes/_authenticated/index.tsx b/frontend/src/routes/_authenticated/index.tsx
index 451eca57..ff2c784f 100644
--- a/frontend/src/routes/_authenticated/index.tsx
+++ b/frontend/src/routes/_authenticated/index.tsx
@@ -13,6 +13,7 @@ import { api } from "@/api"
 import { ChatBox } from "@/components/ChatBox"
 import Sparkle from "@/assets/singleSparkle.svg"
 import { errorComponent } from "@/components/error"
+import { useStateContext } from "@/lib/common"
 
 enum Tabs {
   Search = "search",
@@ -21,7 +22,6 @@ enum Tabs {
 
 const Index = () => {
   const [activeTab, setActiveTab] = useState<Tabs>(Tabs.Ask)
-  const [query, setQuery] = useState("")
 
   const [autocompleteResults, setAutocompleteResults] = useState<
     Autocomplete[]
@@ -36,6 +36,14 @@ const Index = () => {
   const navigate = useNavigate({ from: "/" })
   const matches = useRouterState({ select: (s) => s.matches })
   const { user } = matches[matches.length - 1].context
+  const {
+    stagedFiles,
+    handleFileRemove,
+    handleFileSelection,
+    loading,
+    query,
+    setQuery,
+  } = useStateContext()
 
   useEffect(() => {
     if (!autocompleteQuery) {
@@ -179,6 +187,10 @@ const Index = () => {
                 query={query}
                 setQuery={setQuery}
                 handleSend={handleAsk}
+                stagedFiles={stagedFiles}
+                handleFileSelection={handleFileSelection}
+                handleFileRemove={handleFileRemove}
+                loading={loading}
               />
             </div>
           )}
diff --git a/server/ai/context.ts b/server/ai/context.ts
index 21930532..e774d366 100644
--- a/server/ai/context.ts
+++ b/server/ai/context.ts
@@ -1,11 +1,13 @@
 import type { PublicUserWorkspace } from "@/db/schema"
 import {
+  chatAttachmentSchema,
   eventSchema,
   fileSchema,
   mailAttachmentSchema,
   mailSchema,
   userSchema,
   VespaSearchResultsSchema,
+  type VespaChatAttachmentSearch,
   type VespaEventSearch,
   type VespaFileSearch,
   type VespaMailAttachmentSearch,
@@ -42,6 +44,23 @@ ${fields.chunks_summary && fields.chunks_summary.length ? `Content: ${fields.chu
 \nvespa relevance score: ${relevance}\n`
 }
 
+const constructChatAttachmentContext = (
+  fields: VespaChatAttachmentSearch,
+  relevance: number,
+  maxSummaryChunks?: number,
+): string => {
+  if (!maxSummaryChunks) {
+    maxSummaryChunks = fields.chunks_summary?.length
+  }
+  return `Title: ${fields.title ? `Title: ${fields.title}` : ""}
+Created: ${getRelativeTime(fields.createdAt)}
+Updated At: ${getRelativeTime(fields.updatedAt)}
+${fields.ownerEmail ? `Owner Email: ${fields.ownerEmail}` : ""}
+${fields.mimeType ? `Mime Type: ${fields.mimeType}` : ""}
+${fields.chunks_summary && fields.chunks_summary.length ? `Content: ${fields.chunks_summary.slice(0, maxSummaryChunks).join("\n")}` : ""}
+\nvespa relevance score: ${relevance}\n`
+}
+
 // TODO: tell if workspace that this is an employee
 const constructUserContext = (fields: VespaUser, relevance: number): string => {
   return `App: ${fields.app}
@@ -286,26 +305,35 @@ export const answerContextMap = (
   searchResult: VespaSearchResults,
   maxSummaryChunks?: number,
 ): AiContext => {
-  if (searchResult.fields.sddocname === fileSchema) {
+  if (!searchResult) {
+    return ""
+  }
+  if (searchResult?.fields?.sddocname === fileSchema) {
     return constructFileContext(
-      searchResult.fields,
-      searchResult.relevance,
+      searchResult?.fields,
+      searchResult?.relevance,
       maxSummaryChunks,
     )
-  } else if (searchResult.fields.sddocname === userSchema) {
-    return constructUserContext(searchResult.fields, searchResult.relevance)
-  } else if (searchResult.fields.sddocname === mailSchema) {
+  } else if (searchResult?.fields?.sddocname === userSchema) {
+    return constructUserContext(searchResult?.fields, searchResult?.relevance)
+  } else if (searchResult?.fields?.sddocname === mailSchema) {
     return constructMailContext(
-      searchResult.fields,
-      searchResult.relevance,
+      searchResult?.fields,
+      searchResult?.relevance,
       maxSummaryChunks,
     )
-  } else if (searchResult.fields.sddocname === eventSchema) {
-    return constructEventContext(searchResult.fields, searchResult.relevance)
-  } else if (searchResult.fields.sddocname === mailAttachmentSchema) {
+  } else if (searchResult?.fields?.sddocname === eventSchema) {
+    return constructEventContext(searchResult?.fields, searchResult?.relevance)
+  } else if (searchResult?.fields?.sddocname === chatAttachmentSchema) {
+    return constructChatAttachmentContext(
+      searchResult?.fields,
+      searchResult?.relevance,
+      maxSummaryChunks,
+    )
+  } else if (searchResult?.fields?.sddocname === mailAttachmentSchema) {
     return constructMailAttachmentContext(
-      searchResult.fields,
-      searchResult.relevance,
+      searchResult?.fields,
+      searchResult?.relevance,
       maxSummaryChunks,
     )
   } else {
@@ -323,28 +351,28 @@ export const cleanColoredContext = (text: string): string => {
 
 const cleanVespaHighlights = (text: string): string => {
   const hiTagPattern = /<\/?hi>/g
-  return text.replace(hiTagPattern, "").trim()
+  return text?.replace(hiTagPattern, "").trim()
 }
 const cleanColoredDocs = (text: string): string => {
   const urlPattern =
     /!\[.*?\]\(https:\/\/lh7-rt\.googleusercontent\.com\/docsz\/[a-zA-Z0-9-_?=&]+\)/g
-  let cleanedText = text.replace(urlPattern, "")
+  let cleanedText = text?.replace(urlPattern, "")
 
   // ........
   const extendedEllipsisPattern = /[…\.\s]{2,}/g
-  cleanedText = cleanedText.replace(extendedEllipsisPattern, " ")
+  cleanedText = cleanedText?.replace(extendedEllipsisPattern, " ")
   // .0.0.0.0.0.0.0.0
   const repetitiveDotZeroPattern = /(?:\.0)+(\.\d+)?/g
-  cleanedText = cleanedText.replace(repetitiveDotZeroPattern, "")
+  cleanedText = cleanedText?.replace(repetitiveDotZeroPattern, "")
 
   // Remove control characters
   // Adjusted control characters pattern to exclude ANSI escape codes (\x1B)
   const controlCharsPattern = /[\x00-\x08\x0E-\x1A\x1C-\x1F\x7F-\x9F]/g
-  cleanedText = cleanedText.replace(controlCharsPattern, "")
+  cleanedText = cleanedText?.replace(controlCharsPattern, "")
   // Remove invalid or incomplete UTF characters
   //  and �
   const invalidUtfPattern = /[\uE907\uFFFD]/g
-  cleanedText = cleanedText.replace(invalidUtfPattern, "")
+  cleanedText = cleanedText?.replace(invalidUtfPattern, "")
 
   return cleanedText
 }
@@ -353,22 +381,22 @@ const cleanColoredDocs = (text: string): string => {
 const cleanDocs = (text: string): string => {
   const urlPattern =
     /!\[.*?\]\(https:\/\/lh7-rt\.googleusercontent\.com\/docsz\/[a-zA-Z0-9-_?=&]+\)/g
-  let cleanedText = text.replace(urlPattern, "")
+  let cleanedText = text?.replace(urlPattern, "")
 
   // ........
   const extendedEllipsisPattern = /[…\.\s]{2,}/g
-  cleanedText = cleanedText.replace(extendedEllipsisPattern, " ")
+  cleanedText = cleanedText?.replace(extendedEllipsisPattern, " ")
   // .0.0.0.0.0.0.0.0
   const repetitiveDotZeroPattern = /(?:\.0)+(\.\d+)?/g
-  cleanedText = cleanedText.replace(repetitiveDotZeroPattern, "")
+  cleanedText = cleanedText?.replace(repetitiveDotZeroPattern, "")
 
   // Remove control characters
   const controlCharsPattern = /[\x00-\x1F\x7F-\x9F]/g
-  cleanedText = cleanedText.replace(controlCharsPattern, "")
+  cleanedText = cleanedText?.replace(controlCharsPattern, "")
   // Remove invalid or incomplete UTF characters
   //  and �
   const invalidUtfPattern = /[\uE907\uFFFD]/g
-  cleanedText = cleanedText.replace(invalidUtfPattern, "")
+  cleanedText = cleanedText?.replace(invalidUtfPattern, "")
 
   return cleanedText
 }
@@ -403,7 +431,7 @@ const URL_REGEX: RegExp = /\bhttps?:\/\/[^\s/$.?#].[^\s]*\b/gi
  * @returns The text with URLs replaced by placeholders.
  */
 export const replaceLinks = (text: string): string => {
-  return text.replace(URL_REGEX, (match: string): string => {
+  return text?.replace(URL_REGEX, (match: string): string => {
     try {
       const parsedUrl: URL = new URL(match)
       const domain: string = parsedUrl.hostname
diff --git a/server/api/chat.ts b/server/api/chat.ts
index 7a791762..0077e550 100644
--- a/server/api/chat.ts
+++ b/server/api/chat.ts
@@ -52,15 +52,22 @@ import { HTTPException } from "hono/http-exception"
 import { streamSSE } from "hono/streaming"
 import { z } from "zod"
 import type { chatSchema } from "@/api/search"
-import { searchVespa } from "@/search/vespa"
+import {
+  AddChatMessageIdToAttachment,
+  insert,
+  searchVespa,
+  searchVespaWithChatAttachment,
+} from "@/search/vespa"
 import {
   Apps,
+  chatAttachmentSchema,
   entitySchema,
   eventSchema,
   fileSchema,
   mailAttachmentSchema,
   mailSchema,
   userSchema,
+  type VespaChatAttachment,
   type VespaEvent,
   type VespaEventSearch,
   type VespaFile,
@@ -74,6 +81,12 @@ import {
   type VespaUser,
 } from "@/search/types"
 import { APIError } from "openai"
+import { PDFLoader } from "@langchain/community/document_loaders/fs/pdf"
+import type { Document } from "@langchain/core/documents"
+import { chunkDocument } from "@/chunks"
+import { deleteDocument, downloadDir } from "@/integrations/google"
+import fs from "node:fs"
+import path from "node:path"
 const { JwtPayloadKey, chatHistoryPageSize } = config
 const Logger = getLogger(Subsystem.Chat)
 
@@ -148,6 +161,135 @@ export const GetChatApi = async (c: Context) => {
   }
 }
 
+const blobToBuffer = async (blob: Blob) => {
+  const arrayBuffer = await blob.arrayBuffer() // Convert Blob to ArrayBuffer
+  return Buffer.from(arrayBuffer) // Convert ArrayBuffer to Buffer
+}
+
+const saveToDownloads = async (file: Blob) => {
+  if (!fs.existsSync(downloadDir)) {
+    fs.mkdirSync(downloadDir, { recursive: true })
+  }
+
+  // Define the file path
+  const filePath = path.join(downloadDir, file?.name)
+
+  // Convert the Blob to a Buffer
+  const fileBuffer = await blobToBuffer(file)
+
+  // Save the file
+  try {
+    await fs.promises.writeFile(filePath, new Uint8Array(fileBuffer))
+    Logger.info(`File saved successfully to ${filePath}`)
+  } catch (err) {
+    console.error("Error saving file:", err)
+    await deleteDocument(filePath)
+  }
+}
+
+const getUploadFileDocId = (
+  userEmail: string,
+  fileName: string,
+  dateTime: number,
+) => {
+  return `file_upload_${userEmail}_${fileName}_${dateTime}`
+}
+
+const handlePDFFile = async (file: Blob, userEmail: string) => {
+  let wasDownloaded = false
+  try {
+    // saving the uploaded file in downloads folder
+    await saveToDownloads(file)
+    wasDownloaded = true
+
+    let docs: Document[] = []
+    const filePath = `${downloadDir}/${file?.name}`
+    const loader = new PDFLoader(filePath)
+    docs = await loader.load()
+
+    if (!docs || docs.length === 0) {
+      Logger.error(`Could not get content for file: ${file.name}. Skipping it`)
+      await deleteDocument(filePath)
+      return
+    }
+
+    const chunks = docs.flatMap((doc) => chunkDocument(doc.pageContent))
+
+    const dateTime = new Date().getTime()
+
+    const docId = getUploadFileDocId(userEmail, file?.name, dateTime)
+    const pdfName = `${userEmail}_${file?.name}_${dateTime}`
+
+    const pdfToIngest = {
+      docId: docId,
+      title: pdfName,
+      ownerEmail: userEmail,
+      chunks: chunks.map((v) => v.chunk),
+      mimeType: "application/pdf",
+      createdAt: dateTime,
+      updatedAt: dateTime,
+    }
+
+    // @ts-ignore
+    await insert(pdfToIngest, chatAttachmentSchema)
+
+    // Delete the file here
+    await deleteDocument(filePath)
+
+    // Return metadata
+    // Metadata contains docId, fileName, fileType, fileSize
+    return {
+      docId: docId,
+      fileName: file?.name,
+      fileSize: file?.size,
+      fileType: file?.type,
+    }
+  } catch (err) {
+    if (wasDownloaded) {
+      const filePath = `${downloadDir}/${file?.name}`
+      await deleteDocument(filePath)
+    }
+    Logger.error(
+      `Error handling PDF ${file.name}: ${err} ${(err as Error).stack}`,
+      err,
+    )
+  }
+}
+
+export const UploadFilesApi = async (c: Context) => {
+  try {
+    const { sub } = c.get(JwtPayloadKey)
+    const email = sub
+
+    const formData = await c.req.formData()
+    const files = formData.getAll("files") as File[]
+    const metadata: AttachmentMetadata[] = []
+
+    for (const file of files) {
+      // Parse file according to its type
+      if (file.type === "application/pdf") {
+        const fileMetadata = await handlePDFFile(file, email)
+
+        if (fileMetadata?.docId && fileMetadata?.fileName) {
+          metadata.push(fileMetadata)
+        }
+
+        Logger.info(`Upload file completed`)
+      } else {
+        Logger.error(`File type not supported yet`)
+      }
+    }
+
+    return c.json({ attachmentsMetadata: metadata })
+  } catch (error) {
+    const errMsg = getErrorMessage(error)
+    Logger.error(`Error uploading files: ${errMsg} ${(error as Error).stack}`)
+    throw new HTTPException(500, {
+      message: "Could not upload files",
+    })
+  }
+}
+
 export const ChatRenameApi = async (c: Context) => {
   try {
     // @ts-ignore
@@ -230,12 +372,23 @@ export const ChatBookmarkApi = async (c: Context) => {
 const MinimalCitationSchema = z.object({
   title: z.string().optional(),
   url: z.string().optional(),
-  app: z.nativeEnum(Apps),
-  entity: entitySchema,
+  app: z.nativeEnum(Apps).optional(),
+  entity: entitySchema.optional(),
+  mimeType: z.string().optional(),
+  sddocname: z.string().optional(),
 })
 
 export type Citation = z.infer<typeof MinimalCitationSchema>
 
+const AttachmentMetadataSchema = z.object({
+  docId: z.string(),
+  fileName: z.string(),
+  fileSize: z.number(),
+  fileType: z.string(),
+})
+
+export type AttachmentMetadata = z.infer<typeof AttachmentMetadataSchema>
+
 interface CitationResponse {
   answer?: string
   citations?: number[]
@@ -278,6 +431,12 @@ const searchToCitation = (result: VespaSearchResults): Citation => {
       app: (fields as VespaMailAttachment).app,
       entity: (fields as VespaMailAttachment).entity,
     }
+  } else if (result.fields.sddocname === chatAttachmentSchema) {
+    return {
+      title: (fields as VespaChatAttachment).title,
+      sddocname: fields.sddocname,
+      mimeType: (fields as VespaChatAttachment).mimeType || "",
+    }
   } else {
     throw new Error("Invalid search result type for citation")
   }
@@ -315,6 +474,7 @@ async function* generateIterativeTimeFilterAndQueryRewrite(
   pageSize: number = 10,
   maxPageNumber: number = 3,
   maxSummaryCount: number | undefined,
+  chatExtId: string,
 ): AsyncIterableIterator<
   ConverseResponse & { citation?: { index: number; item: any } }
 > {
@@ -335,19 +495,37 @@ async function* generateIterativeTimeFilterAndQueryRewrite(
     ?.map((v: VespaSearchResult) => (v?.fields as any).docId)
     ?.filter((v) => !!v)
 
+  // Condition to decide if searchVespa function will be used to search or searchVespaWithChatAttachment
+  // If Chat has attachment then we use searchVespaWithChatAttachment, otherwise searchVespa
+
+  // Check if the current chat has attachments
+  const currentChat = await getChatByExternalId(db, chatExtId)
+  const currentChatHasAttachments = currentChat?.hasAttachments
+
   for (var pageNumber = 0; pageNumber < maxPageNumber; pageNumber++) {
     // should only do it once
     if (pageNumber === Math.floor(maxPageNumber / 2)) {
       // get the first page of results
-      let results = await searchVespa(
-        message,
-        email,
-        null,
-        null,
-        pageSize,
-        0,
-        alpha,
-      )
+      let results
+      if (currentChatHasAttachments) {
+        results = await searchVespaWithChatAttachment(
+          message,
+          email,
+          chatExtId,
+          pageSize,
+          0,
+        )
+      } else {
+        results = await searchVespa(
+          message,
+          email,
+          null,
+          null,
+          pageSize,
+          0,
+          alpha,
+        )
+      }
       const initialContext = cleanContext(
         results?.root?.children
           ?.map(
@@ -362,26 +540,51 @@ async function* generateIterativeTimeFilterAndQueryRewrite(
       })
       const queries = queryResp.queries
       for (const query of queries) {
-        const latestResults: VespaSearchResult[] = (
-          await searchVespa(query, email, null, null, pageSize, 0, alpha, {
-            from: new Date().getTime() - 4 * monthInMs,
-            to: new Date().getTime(),
-          })
-        )?.root?.children
+        let latestResults: VespaSearchResult[]
+        if (currentChatHasAttachments) {
+          latestResults = (
+            await searchVespaWithChatAttachment(
+              message,
+              email,
+              chatExtId,
+              pageSize,
+              0,
+            )
+          )?.root?.children
+        } else {
+          latestResults = (
+            await searchVespa(query, email, null, null, pageSize, 0, alpha, {
+              from: new Date().getTime() - 4 * monthInMs,
+              to: new Date().getTime(),
+            })
+          )?.root?.children
+        }
+
+        let results
+        if (currentChatHasAttachments) {
+          results = await searchVespaWithChatAttachment(
+            message,
+            email,
+            chatExtId,
+            pageSize,
+            0,
+          )
+        } else {
+          results = await searchVespa(
+            query,
+            email,
+            null,
+            null,
+            pageSize,
+            0,
+            alpha,
+            null,
+            latestResults
+              ?.map((v: VespaSearchResult) => (v.fields as any).docId)
+              ?.filter((v) => !!v),
+          )
+        }
 
-        let results = await searchVespa(
-          query,
-          email,
-          null,
-          null,
-          pageSize,
-          0,
-          alpha,
-          null,
-          latestResults
-            ?.map((v: VespaSearchResult) => (v.fields as any).docId)
-            ?.filter((v) => !!v),
-        )
         const totalResults = results?.root?.children?.concat(latestResults)
         const initialContext = cleanContext(
           totalResults
@@ -465,31 +668,51 @@ async function* generateIterativeTimeFilterAndQueryRewrite(
 
     let results: VespaSearchResponse
     if (pageNumber === 0) {
-      results = await searchVespa(
-        message,
-        email,
-        null,
-        null,
-        pageSize,
-        pageNumber * pageSize,
-        alpha,
-        null,
-        latestIds,
-      )
+      if (currentChatHasAttachments) {
+        results = await searchVespaWithChatAttachment(
+          message,
+          email,
+          chatExtId,
+          pageSize,
+          pageNumber * pageSize,
+        )
+      } else {
+        results = await searchVespa(
+          message,
+          email,
+          null,
+          null,
+          pageSize,
+          pageNumber * pageSize,
+          alpha,
+          null,
+          latestIds,
+        )
+      }
       if (!results.root.children) {
         results.root.children = []
       }
       results.root.children = results?.root?.children?.concat(latestResults)
     } else {
-      results = await searchVespa(
-        message,
-        email,
-        null,
-        null,
-        pageSize,
-        pageNumber * pageSize,
-        alpha,
-      )
+      if (currentChatHasAttachments) {
+        results = await searchVespaWithChatAttachment(
+          message,
+          email,
+          chatExtId,
+          pageSize,
+          pageNumber * pageSize,
+        )
+      } else {
+        results = await searchVespa(
+          message,
+          email,
+          null,
+          null,
+          pageSize,
+          pageNumber * pageSize,
+          alpha,
+        )
+      }
     }
     const initialContext = cleanContext(
       results?.root?.children
@@ -770,6 +993,7 @@ export async function* UnderstandMessageAndAnswer(
   message: string,
   classification: TemporalClassifier & { cost: number },
   messages: Message[],
+  chatExtId: string,
 ): AsyncIterableIterator<
   ConverseResponse & { citation?: { index: number; item: any } }
 > {
@@ -802,6 +1026,7 @@ export async function* UnderstandMessageAndAnswer(
       20,
       3,
       5,
+      chatExtId,
     )
   }
 }
@@ -837,7 +1062,7 @@ export const MessageApi = async (c: Context) => {
     const email = sub
     // @ts-ignore
     const body = c.req.valid("query")
-    let { message, chatId, modelId }: MessageReqType = body
+    let { message, chatId, modelId, attachments }: MessageReqType = body
     if (!message) {
       throw new HTTPException(400, {
         message: "Message is required",
@@ -871,6 +1096,7 @@ export const MessageApi = async (c: Context) => {
 
       let [insertedChat, insertedMsg] = await db.transaction(
         async (tx): Promise<[SelectChat, SelectMessage]> => {
+          const attachmentsToBeInserted = JSON.parse(attachments) || []
           const chat = await insertChat(tx, {
             workspaceId: workspace.id,
             workspaceExternalId: workspace.externalId,
@@ -878,6 +1104,7 @@ export const MessageApi = async (c: Context) => {
             email: user.email,
             title,
             attachments: [],
+            hasAttachments: attachmentsToBeInserted?.length > 0 ? true : false,
           })
           const insertedMsg = await insertMessage(tx, {
             chatId: chat.id,
@@ -886,10 +1113,24 @@ export const MessageApi = async (c: Context) => {
             workspaceExternalId: workspace.externalId,
             messageRole: MessageRole.User,
             email: user.email,
-            sources: [],
+            sources: attachmentsToBeInserted, // Adding attachmentMetadata to sources
+            attachments: attachmentsToBeInserted,
             message,
             modelId,
           })
+
+          // Add this to chatAttachments in vespa
+          const chatExtId = chat.externalId
+          const messageExtId = insertedMsg.externalId
+          for (const attachment of attachmentsToBeInserted) {
+            const attachmentId = attachment?.docId
+            await AddChatMessageIdToAttachment(
+              chatAttachmentSchema,
+              attachmentId,
+              chatExtId,
+              messageExtId,
+            )
+          }
           return [chat, insertedMsg]
         },
       )
@@ -901,8 +1142,21 @@ export const MessageApi = async (c: Context) => {
     } else {
       let [existingChat, allMessages, insertedMsg] = await db.transaction(
         async (tx): Promise<[SelectChat, SelectMessage[], SelectMessage]> => {
+          const newAttachments = JSON.parse(attachments) || []
+
+          const oldChat = await getChatByExternalId(db, chatId)
+          const alreadyHasAttachments = oldChat?.hasAttachments
+          const hasAttachmentsNow = newAttachments?.length > 0 ? true : false
           // we are updating the chat and getting it's value in one call itself
-          let existingChat = await updateChatByExternalId(db, chatId, {})
+          let existingChat = await updateChatByExternalId(
+            db,
+            chatId,
+            alreadyHasAttachments
+              ? {}
+              : hasAttachmentsNow
+                ? { hasAttachments: hasAttachmentsNow }
+                : {},
+          )
           let allMessages = await getChatMessages(tx, chatId)
           let insertedMsg = await insertMessage(tx, {
             chatId: existingChat.id,
@@ -911,10 +1165,24 @@ export const MessageApi = async (c: Context) => {
             chatExternalId: existingChat.externalId,
             messageRole: MessageRole.User,
             email: user.email,
-            sources: [],
+            sources: newAttachments, // Adding new attachments metadata
+            attachments: newAttachments,
             message,
             modelId,
           })
+
+          // Add this to chatAttachments in vespa
+          const chatExtId = existingChat.externalId
+          const messageExtId = insertedMsg.externalId
+          for (const attachment of newAttachments) {
+            const attachmentId = attachment?.docId
+            await AddChatMessageIdToAttachment(
+              chatAttachmentSchema,
+              attachmentId,
+              chatExtId,
+              messageExtId,
+            )
+          }
           return [existingChat, allMessages, insertedMsg]
         },
       )
@@ -1039,6 +1307,7 @@ export const MessageApi = async (c: Context) => {
               message,
               classification,
               messagesWithNoErrResponse,
+              chat?.externalId,
             )
 
             stream.writeSSE({
@@ -1395,6 +1664,7 @@ export const MessageRetryApi = async (c: Context) => {
               message,
               classification,
               convWithNoErrMsg,
+              originalMessage.chatExternalId,
             )
             // throw new Error("Hello, how are u doing?")
             stream.writeSSE({
diff --git a/server/api/search.ts b/server/api/search.ts
index 7b58c6a0..cff2bde6 100644
--- a/server/api/search.ts
+++ b/server/api/search.ts
@@ -94,6 +94,7 @@ export const messageSchema = z.object({
   message: z.string().min(1),
   chatId: z.string().optional(),
   modelId: z.string().min(1),
+  attachments: z.string(),
 })
 export type MessageReqType = z.infer<typeof messageSchema>
 
@@ -101,6 +102,16 @@ export const messageRetrySchema = z.object({
   messageId: z.string().min(1),
 })
 
+const uploadFileSchema = z.object({
+  name: z.string(),
+  size: z.number(),
+  type: z.string(),
+})
+
+export const fileUploadSchema = z.object({
+  files: uploadFileSchema.or(z.array(uploadFileSchema)),
+})
+
 export const AutocompleteApi = async (c: Context) => {
   try {
     const { sub } = c.get(JwtPayloadKey)
diff --git a/server/bun.lockb b/server/bun.lockb
index 9f7fab0f..06a9bdc1 100755
Binary files a/server/bun.lockb and b/server/bun.lockb differ
diff --git a/server/db/schema.ts b/server/db/schema.ts
index 61ec037e..1870a7b5 100644
--- a/server/db/schema.ts
+++ b/server/db/schema.ts
@@ -292,6 +292,7 @@ export const chats = pgTable(
       .notNull()
       .default(sql`NOW()`),
     deletedAt: timestamp("deleted_at", { withTimezone: true }),
+    hasAttachments: boolean("hasAttachments").notNull().default(false),
   },
   (table) => ({
     isBookmarkedIndex: index("is_bookmarked_index").on(table.isBookmarked),
@@ -324,6 +325,7 @@ export const messages = pgTable(
     modelId: text("modelId").notNull(),
     email: text("email").notNull(),
     sources: jsonb("sources").notNull().default(sql`'[]'::jsonb`),
+    attachments: jsonb("attachments").notNull().default(sql`'[]'::jsonb`),
     createdAt: timestamp("created_at", { withTimezone: true })
       .notNull()
       .default(sql`NOW()`),
diff --git a/server/migrations/0001_dark_maddog.sql b/server/migrations/0001_dark_maddog.sql
new file mode 100644
index 00000000..4db0dd96
--- /dev/null
+++ b/server/migrations/0001_dark_maddog.sql
@@ -0,0 +1,2 @@
+ALTER TABLE "chats" ADD COLUMN "hasAttachments" boolean DEFAULT false NOT NULL;--> statement-breakpoint
+ALTER TABLE "messages" ADD COLUMN "attachments" jsonb DEFAULT '[]'::jsonb NOT NULL;
\ No newline at end of file
diff --git a/server/migrations/meta/0000_snapshot.json b/server/migrations/meta/0000_snapshot.json
index 71cbc4e3..cbc888d0 100644
--- a/server/migrations/meta/0000_snapshot.json
+++ b/server/migrations/meta/0000_snapshot.json
@@ -106,12 +106,8 @@
           "name": "chats_workspace_id_workspaces_id_fk",
           "tableFrom": "chats",
           "tableTo": "workspaces",
-          "columnsFrom": [
-            "workspace_id"
-          ],
-          "columnsTo": [
-            "id"
-          ],
+          "columnsFrom": ["workspace_id"],
+          "columnsTo": ["id"],
           "onDelete": "no action",
           "onUpdate": "no action"
         },
@@ -119,12 +115,8 @@
           "name": "chats_user_id_users_id_fk",
           "tableFrom": "chats",
           "tableTo": "users",
-          "columnsFrom": [
-            "user_id"
-          ],
-          "columnsTo": [
-            "id"
-          ],
+          "columnsFrom": ["user_id"],
+          "columnsTo": ["id"],
           "onDelete": "no action",
           "onUpdate": "no action"
         }
@@ -134,9 +126,7 @@
         "chats_external_id_unique": {
           "name": "chats_external_id_unique",
           "nullsNotDistinct": false,
-          "columns": [
-            "external_id"
-          ]
+          "columns": ["external_id"]
         }
       }
     },
@@ -254,12 +244,8 @@
           "name": "connectors_workspace_id_workspaces_id_fk",
           "tableFrom": "connectors",
           "tableTo": "workspaces",
-          "columnsFrom": [
-            "workspace_id"
-          ],
-          "columnsTo": [
-            "id"
-          ],
+          "columnsFrom": ["workspace_id"],
+          "columnsTo": ["id"],
           "onDelete": "no action",
           "onUpdate": "no action"
         },
@@ -267,12 +253,8 @@
           "name": "connectors_user_id_users_id_fk",
           "tableFrom": "connectors",
           "tableTo": "users",
-          "columnsFrom": [
-            "user_id"
-          ],
-          "columnsTo": [
-            "id"
-          ],
+          "columnsFrom": ["user_id"],
+          "columnsTo": ["id"],
           "onDelete": "no action",
           "onUpdate": "no action"
         }
@@ -282,19 +264,12 @@
         "connectors_external_id_unique": {
           "name": "connectors_external_id_unique",
           "nullsNotDistinct": false,
-          "columns": [
-            "external_id"
-          ]
+          "columns": ["external_id"]
         },
         "connectors_workspace_id_user_id_app_type_auth_type_unique": {
           "name": "connectors_workspace_id_user_id_app_type_auth_type_unique",
           "nullsNotDistinct": false,
-          "columns": [
-            "workspace_id",
-            "user_id",
-            "app_type",
-            "auth_type"
-          ]
+          "columns": ["workspace_id", "user_id", "app_type", "auth_type"]
         }
       }
     },
@@ -420,12 +395,8 @@
           "name": "messages_chat_id_chats_id_fk",
           "tableFrom": "messages",
           "tableTo": "chats",
-          "columnsFrom": [
-            "chat_id"
-          ],
-          "columnsTo": [
-            "id"
-          ],
+          "columnsFrom": ["chat_id"],
+          "columnsTo": ["id"],
           "onDelete": "no action",
           "onUpdate": "no action"
         },
@@ -433,12 +404,154 @@
           "name": "messages_user_id_users_id_fk",
           "tableFrom": "messages",
           "tableTo": "users",
-          "columnsFrom": [
-            "user_id"
-          ],
-          "columnsTo": [
-            "id"
+          "columnsFrom": ["user_id"],
+          "columnsTo": ["id"],
+          "onDelete": "no action",
+          "onUpdate": "no action"
+        }
+      },
+      "compositePrimaryKeys": {},
+      "uniqueConstraints": {
+        "messages_external_id_unique": {
+          "name": "messages_external_id_unique",
+          "nullsNotDistinct": false,
+          "columns": ["external_id"]
+        }
+      }
+    },
+    "public.messages": {
+      "name": "messages",
+      "schema": "",
+      "columns": {
+        "id": {
+          "name": "id",
+          "type": "serial",
+          "primaryKey": true,
+          "notNull": true
+        },
+        "chat_id": {
+          "name": "chat_id",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "user_id": {
+          "name": "user_id",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "external_id": {
+          "name": "external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "workspace_external_id": {
+          "name": "workspace_external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "chat_external_id": {
+          "name": "chat_external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "message": {
+          "name": "message",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "message_role": {
+          "name": "message_role",
+          "type": "message_role",
+          "typeSchema": "public",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "modelId": {
+          "name": "modelId",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "email": {
+          "name": "email",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "sources": {
+          "name": "sources",
+          "type": "jsonb",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "'[]'::jsonb"
+        },
+        "created_at": {
+          "name": "created_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        },
+        "updated_at": {
+          "name": "updated_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        },
+        "deleted_at": {
+          "name": "deleted_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": false
+        },
+        "error_message": {
+          "name": "error_message",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": false,
+          "default": "''"
+        }
+      },
+      "indexes": {
+        "chat_id_index": {
+          "name": "chat_id_index",
+          "columns": [
+            {
+              "expression": "chat_id",
+              "isExpression": false,
+              "asc": true,
+              "nulls": "last"
+            }
           ],
+          "isUnique": false,
+          "concurrently": false,
+          "method": "btree",
+          "with": {}
+        }
+      },
+      "foreignKeys": {
+        "messages_chat_id_chats_id_fk": {
+          "name": "messages_chat_id_chats_id_fk",
+          "tableFrom": "messages",
+          "tableTo": "chats",
+          "columnsFrom": ["chat_id"],
+          "columnsTo": ["id"],
+          "onDelete": "no action",
+          "onUpdate": "no action"
+        },
+        "messages_user_id_users_id_fk": {
+          "name": "messages_user_id_users_id_fk",
+          "tableFrom": "messages",
+          "tableTo": "users",
+          "columnsFrom": ["user_id"],
+          "columnsTo": ["id"],
           "onDelete": "no action",
           "onUpdate": "no action"
         }
@@ -448,9 +561,153 @@
         "messages_external_id_unique": {
           "name": "messages_external_id_unique",
           "nullsNotDistinct": false,
+          "columns": ["external_id"]
+        }
+      }
+    },
+    "public.messages": {
+      "name": "messages",
+      "schema": "",
+      "columns": {
+        "id": {
+          "name": "id",
+          "type": "serial",
+          "primaryKey": true,
+          "notNull": true
+        },
+        "chat_id": {
+          "name": "chat_id",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "user_id": {
+          "name": "user_id",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "external_id": {
+          "name": "external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "workspace_external_id": {
+          "name": "workspace_external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "chat_external_id": {
+          "name": "chat_external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "message": {
+          "name": "message",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "message_role": {
+          "name": "message_role",
+          "type": "message_role",
+          "typeSchema": "public",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "modelId": {
+          "name": "modelId",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "email": {
+          "name": "email",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "sources": {
+          "name": "sources",
+          "type": "jsonb",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "'[]'::jsonb"
+        },
+        "created_at": {
+          "name": "created_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        },
+        "updated_at": {
+          "name": "updated_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        },
+        "deleted_at": {
+          "name": "deleted_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": false
+        },
+        "error_message": {
+          "name": "error_message",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": false,
+          "default": "''"
+        }
+      },
+      "indexes": {
+        "chat_id_index": {
+          "name": "chat_id_index",
           "columns": [
-            "external_id"
-          ]
+            {
+              "expression": "chat_id",
+              "isExpression": false,
+              "asc": true,
+              "nulls": "last"
+            }
+          ],
+          "isUnique": false,
+          "concurrently": false,
+          "method": "btree",
+          "with": {}
+        }
+      },
+      "foreignKeys": {
+        "messages_chat_id_chats_id_fk": {
+          "name": "messages_chat_id_chats_id_fk",
+          "tableFrom": "messages",
+          "tableTo": "chats",
+          "columnsFrom": ["chat_id"],
+          "columnsTo": ["id"],
+          "onDelete": "no action",
+          "onUpdate": "no action"
+        },
+        "messages_user_id_users_id_fk": {
+          "name": "messages_user_id_users_id_fk",
+          "tableFrom": "messages",
+          "tableTo": "users",
+          "columnsFrom": ["user_id"],
+          "columnsTo": ["id"],
+          "onDelete": "no action",
+          "onUpdate": "no action"
+        }
+      },
+      "compositePrimaryKeys": {},
+      "uniqueConstraints": {
+        "messages_external_id_unique": {
+          "name": "messages_external_id_unique",
+          "nullsNotDistinct": false,
+          "columns": ["external_id"]
         }
       }
     },
@@ -541,12 +798,8 @@
           "name": "oauth_providers_workspace_id_workspaces_id_fk",
           "tableFrom": "oauth_providers",
           "tableTo": "workspaces",
-          "columnsFrom": [
-            "workspace_id"
-          ],
-          "columnsTo": [
-            "id"
-          ],
+          "columnsFrom": ["workspace_id"],
+          "columnsTo": ["id"],
           "onDelete": "no action",
           "onUpdate": "no action"
         },
@@ -554,12 +807,8 @@
           "name": "oauth_providers_user_id_users_id_fk",
           "tableFrom": "oauth_providers",
           "tableTo": "users",
-          "columnsFrom": [
-            "user_id"
-          ],
-          "columnsTo": [
-            "id"
-          ],
+          "columnsFrom": ["user_id"],
+          "columnsTo": ["id"],
           "onDelete": "no action",
           "onUpdate": "no action"
         },
@@ -567,12 +816,8 @@
           "name": "oauth_providers_container_id_connectors_id_fk",
           "tableFrom": "oauth_providers",
           "tableTo": "connectors",
-          "columnsFrom": [
-            "container_id"
-          ],
-          "columnsTo": [
-            "id"
-          ],
+          "columnsFrom": ["container_id"],
+          "columnsTo": ["id"],
           "onDelete": "no action",
           "onUpdate": "no action"
         }
@@ -582,9 +827,7 @@
         "oauth_providers_external_id_unique": {
           "name": "oauth_providers_external_id_unique",
           "nullsNotDistinct": false,
-          "columns": [
-            "external_id"
-          ]
+          "columns": ["external_id"]
         }
       }
     },
@@ -718,12 +961,8 @@
           "name": "sync_history_workspace_id_workspaces_id_fk",
           "tableFrom": "sync_history",
           "tableTo": "workspaces",
-          "columnsFrom": [
-            "workspace_id"
-          ],
-          "columnsTo": [
-            "id"
-          ],
+          "columnsFrom": ["workspace_id"],
+          "columnsTo": ["id"],
           "onDelete": "no action",
           "onUpdate": "no action"
         }
@@ -733,9 +972,7 @@
         "sync_history_external_id_unique": {
           "name": "sync_history_external_id_unique",
           "nullsNotDistinct": false,
-          "columns": [
-            "external_id"
-          ]
+          "columns": ["external_id"]
         }
       }
     },
@@ -848,12 +1085,8 @@
           "name": "sync_jobs_workspace_id_workspaces_id_fk",
           "tableFrom": "sync_jobs",
           "tableTo": "workspaces",
-          "columnsFrom": [
-            "workspace_id"
-          ],
-          "columnsTo": [
-            "id"
-          ],
+          "columnsFrom": ["workspace_id"],
+          "columnsTo": ["id"],
           "onDelete": "no action",
           "onUpdate": "no action"
         },
@@ -861,12 +1094,8 @@
           "name": "sync_jobs_connector_id_connectors_id_fk",
           "tableFrom": "sync_jobs",
           "tableTo": "connectors",
-          "columnsFrom": [
-            "connector_id"
-          ],
-          "columnsTo": [
-            "id"
-          ],
+          "columnsFrom": ["connector_id"],
+          "columnsTo": ["id"],
           "onDelete": "no action",
           "onUpdate": "no action"
         }
@@ -876,9 +1105,7 @@
         "sync_jobs_external_id_unique": {
           "name": "sync_jobs_external_id_unique",
           "nullsNotDistinct": false,
-          "columns": [
-            "external_id"
-          ]
+          "columns": ["external_id"]
         }
       }
     },
@@ -986,12 +1213,8 @@
           "name": "users_workspace_id_workspaces_id_fk",
           "tableFrom": "users",
           "tableTo": "workspaces",
-          "columnsFrom": [
-            "workspace_id"
-          ],
-          "columnsTo": [
-            "id"
-          ],
+          "columnsFrom": ["workspace_id"],
+          "columnsTo": ["id"],
           "onDelete": "no action",
           "onUpdate": "no action"
         }
@@ -1001,9 +1224,7 @@
         "users_external_id_unique": {
           "name": "users_external_id_unique",
           "nullsNotDistinct": false,
-          "columns": [
-            "external_id"
-          ]
+          "columns": ["external_id"]
         }
       }
     },
@@ -1047,6 +1268,12 @@
           "primaryKey": false,
           "notNull": false
         },
+        "photoLink": {
+          "name": "photoLink",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": false
+        },
         "created_at": {
           "name": "created_at",
           "type": "timestamp with time zone",
@@ -1075,23 +1302,17 @@
         "workspaces_domain_unique": {
           "name": "workspaces_domain_unique",
           "nullsNotDistinct": false,
-          "columns": [
-            "domain"
-          ]
+          "columns": ["domain"]
         },
         "workspaces_created_by_unique": {
           "name": "workspaces_created_by_unique",
           "nullsNotDistinct": false,
-          "columns": [
-            "created_by"
-          ]
+          "columns": ["created_by"]
         },
         "workspaces_external_id_unique": {
           "name": "workspaces_external_id_unique",
           "nullsNotDistinct": false,
-          "columns": [
-            "external_id"
-          ]
+          "columns": ["external_id"]
         }
       }
     }
@@ -1111,71 +1332,47 @@
     "public.auth_type": {
       "name": "auth_type",
       "schema": "public",
-      "values": [
-        "oauth",
-        "service_account",
-        "custom",
-        "api_key"
-      ]
+      "values": ["oauth", "service_account", "custom", "api_key"]
     },
     "public.connector_type": {
       "name": "connector_type",
       "schema": "public",
-      "values": [
-        "SaaS",
-        "Database",
-        "Api",
-        "File",
-        "Website"
-      ]
+      "values": ["SaaS", "Database", "Api", "File", "Website"]
     },
     "public.message_role": {
       "name": "message_role",
       "schema": "public",
-      "values": [
-        "system",
-        "user",
-        "assistant"
-      ]
+      "values": ["system", "user", "assistant"]
+    },
+    "public.message_role": {
+      "name": "message_role",
+      "schema": "public",
+      "values": ["system", "user", "assistant"]
+    },
+    "public.message_role": {
+      "name": "message_role",
+      "schema": "public",
+      "values": ["system", "user", "assistant"]
     },
     "public.status": {
       "name": "status",
       "schema": "public",
-      "values": [
-        "connected",
-        "connecting",
-        "failed",
-        "not-connected"
-      ]
+      "values": ["connected", "connecting", "failed", "not-connected"]
     },
     "public.type": {
       "name": "type",
       "schema": "public",
-      "values": [
-        "ChangeToken",
-        "Partial",
-        "FullSync"
-      ]
+      "values": ["ChangeToken", "Partial", "FullSync"]
     },
     "public.sync_status": {
       "name": "sync_status",
       "schema": "public",
-      "values": [
-        "NotStarted",
-        "Started",
-        "Failed",
-        "Successful"
-      ]
+      "values": ["NotStarted", "Started", "Failed", "Successful"]
     },
     "public.role": {
       "name": "role",
       "schema": "public",
-      "values": [
-        "User",
-        "TeamLeader",
-        "Admin",
-        "SuperAdmin"
-      ]
+      "values": ["User", "TeamLeader", "Admin", "SuperAdmin"]
     }
   },
   "schemas": {},
@@ -1185,4 +1382,4 @@
     "schemas": {},
     "tables": {}
   }
-}
\ No newline at end of file
+}
diff --git a/server/migrations/meta/0001_snapshot.json b/server/migrations/meta/0001_snapshot.json
new file mode 100644
index 00000000..b2d05a28
--- /dev/null
+++ b/server/migrations/meta/0001_snapshot.json
@@ -0,0 +1,1202 @@
+{
+  "id": "9d2eb298-7917-47bd-96a4-c881a9306e97",
+  "prevId": "69339c64-d4cd-4467-8254-4d0d14b3de69",
+  "version": "7",
+  "dialect": "postgresql",
+  "tables": {
+    "public.chats": {
+      "name": "chats",
+      "schema": "",
+      "columns": {
+        "id": {
+          "name": "id",
+          "type": "serial",
+          "primaryKey": true,
+          "notNull": true
+        },
+        "workspace_id": {
+          "name": "workspace_id",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "user_id": {
+          "name": "user_id",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "external_id": {
+          "name": "external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "workspace_external_id": {
+          "name": "workspace_external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "is_bookmarked": {
+          "name": "is_bookmarked",
+          "type": "boolean",
+          "primaryKey": false,
+          "notNull": true,
+          "default": false
+        },
+        "email": {
+          "name": "email",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "title": {
+          "name": "title",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "attachments": {
+          "name": "attachments",
+          "type": "jsonb",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "created_at": {
+          "name": "created_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        },
+        "updated_at": {
+          "name": "updated_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        },
+        "deleted_at": {
+          "name": "deleted_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": false
+        },
+        "hasAttachments": {
+          "name": "hasAttachments",
+          "type": "boolean",
+          "primaryKey": false,
+          "notNull": true,
+          "default": false
+        }
+      },
+      "indexes": {
+        "is_bookmarked_index": {
+          "name": "is_bookmarked_index",
+          "columns": [
+            {
+              "expression": "is_bookmarked",
+              "isExpression": false,
+              "asc": true,
+              "nulls": "last"
+            }
+          ],
+          "isUnique": false,
+          "concurrently": false,
+          "method": "btree",
+          "with": {}
+        }
+      },
+      "foreignKeys": {
+        "chats_workspace_id_workspaces_id_fk": {
+          "name": "chats_workspace_id_workspaces_id_fk",
+          "tableFrom": "chats",
+          "tableTo": "workspaces",
+          "columnsFrom": [
+            "workspace_id"
+          ],
+          "columnsTo": [
+            "id"
+          ],
+          "onDelete": "no action",
+          "onUpdate": "no action"
+        },
+        "chats_user_id_users_id_fk": {
+          "name": "chats_user_id_users_id_fk",
+          "tableFrom": "chats",
+          "tableTo": "users",
+          "columnsFrom": [
+            "user_id"
+          ],
+          "columnsTo": [
+            "id"
+          ],
+          "onDelete": "no action",
+          "onUpdate": "no action"
+        }
+      },
+      "compositePrimaryKeys": {},
+      "uniqueConstraints": {
+        "chats_external_id_unique": {
+          "name": "chats_external_id_unique",
+          "nullsNotDistinct": false,
+          "columns": [
+            "external_id"
+          ]
+        }
+      }
+    },
+    "public.connectors": {
+      "name": "connectors",
+      "schema": "",
+      "columns": {
+        "id": {
+          "name": "id",
+          "type": "serial",
+          "primaryKey": true,
+          "notNull": true
+        },
+        "workspace_id": {
+          "name": "workspace_id",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "user_id": {
+          "name": "user_id",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "external_id": {
+          "name": "external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "workspace_external_id": {
+          "name": "workspace_external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "name": {
+          "name": "name",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "type": {
+          "name": "type",
+          "type": "connector_type",
+          "typeSchema": "public",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "auth_type": {
+          "name": "auth_type",
+          "type": "auth_type",
+          "typeSchema": "public",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "app_type": {
+          "name": "app_type",
+          "type": "app_type",
+          "typeSchema": "public",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "config": {
+          "name": "config",
+          "type": "jsonb",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "credentials": {
+          "name": "credentials",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": false
+        },
+        "subject": {
+          "name": "subject",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": false
+        },
+        "oauth_credentials": {
+          "name": "oauth_credentials",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": false
+        },
+        "status": {
+          "name": "status",
+          "type": "status",
+          "typeSchema": "public",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "'connecting'"
+        },
+        "created_at": {
+          "name": "created_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        },
+        "updated_at": {
+          "name": "updated_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        }
+      },
+      "indexes": {},
+      "foreignKeys": {
+        "connectors_workspace_id_workspaces_id_fk": {
+          "name": "connectors_workspace_id_workspaces_id_fk",
+          "tableFrom": "connectors",
+          "tableTo": "workspaces",
+          "columnsFrom": [
+            "workspace_id"
+          ],
+          "columnsTo": [
+            "id"
+          ],
+          "onDelete": "no action",
+          "onUpdate": "no action"
+        },
+        "connectors_user_id_users_id_fk": {
+          "name": "connectors_user_id_users_id_fk",
+          "tableFrom": "connectors",
+          "tableTo": "users",
+          "columnsFrom": [
+            "user_id"
+          ],
+          "columnsTo": [
+            "id"
+          ],
+          "onDelete": "no action",
+          "onUpdate": "no action"
+        }
+      },
+      "compositePrimaryKeys": {},
+      "uniqueConstraints": {
+        "connectors_external_id_unique": {
+          "name": "connectors_external_id_unique",
+          "nullsNotDistinct": false,
+          "columns": [
+            "external_id"
+          ]
+        },
+        "connectors_workspace_id_user_id_app_type_auth_type_unique": {
+          "name": "connectors_workspace_id_user_id_app_type_auth_type_unique",
+          "nullsNotDistinct": false,
+          "columns": [
+            "workspace_id",
+            "user_id",
+            "app_type",
+            "auth_type"
+          ]
+        }
+      }
+    },
+    "public.messages": {
+      "name": "messages",
+      "schema": "",
+      "columns": {
+        "id": {
+          "name": "id",
+          "type": "serial",
+          "primaryKey": true,
+          "notNull": true
+        },
+        "chat_id": {
+          "name": "chat_id",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "user_id": {
+          "name": "user_id",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "external_id": {
+          "name": "external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "workspace_external_id": {
+          "name": "workspace_external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "chat_external_id": {
+          "name": "chat_external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "message": {
+          "name": "message",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "message_role": {
+          "name": "message_role",
+          "type": "message_role",
+          "typeSchema": "public",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "modelId": {
+          "name": "modelId",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "email": {
+          "name": "email",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "sources": {
+          "name": "sources",
+          "type": "jsonb",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "'[]'::jsonb"
+        },
+        "attachments": {
+          "name": "attachments",
+          "type": "jsonb",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "'[]'::jsonb"
+        },
+        "created_at": {
+          "name": "created_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        },
+        "updated_at": {
+          "name": "updated_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        },
+        "deleted_at": {
+          "name": "deleted_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": false
+        },
+        "error_message": {
+          "name": "error_message",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": false,
+          "default": "''"
+        }
+      },
+      "indexes": {
+        "chat_id_index": {
+          "name": "chat_id_index",
+          "columns": [
+            {
+              "expression": "chat_id",
+              "isExpression": false,
+              "asc": true,
+              "nulls": "last"
+            }
+          ],
+          "isUnique": false,
+          "concurrently": false,
+          "method": "btree",
+          "with": {}
+        }
+      },
+      "foreignKeys": {
+        "messages_chat_id_chats_id_fk": {
+          "name": "messages_chat_id_chats_id_fk",
+          "tableFrom": "messages",
+          "tableTo": "chats",
+          "columnsFrom": [
+            "chat_id"
+          ],
+          "columnsTo": [
+            "id"
+          ],
+          "onDelete": "no action",
+          "onUpdate": "no action"
+        },
+        "messages_user_id_users_id_fk": {
+          "name": "messages_user_id_users_id_fk",
+          "tableFrom": "messages",
+          "tableTo": "users",
+          "columnsFrom": [
+            "user_id"
+          ],
+          "columnsTo": [
+            "id"
+          ],
+          "onDelete": "no action",
+          "onUpdate": "no action"
+        }
+      },
+      "compositePrimaryKeys": {},
+      "uniqueConstraints": {
+        "messages_external_id_unique": {
+          "name": "messages_external_id_unique",
+          "nullsNotDistinct": false,
+          "columns": [
+            "external_id"
+          ]
+        }
+      }
+    },
+    "public.oauth_providers": {
+      "name": "oauth_providers",
+      "schema": "",
+      "columns": {
+        "id": {
+          "name": "id",
+          "type": "serial",
+          "primaryKey": true,
+          "notNull": true
+        },
+        "workspace_id": {
+          "name": "workspace_id",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "user_id": {
+          "name": "user_id",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "external_id": {
+          "name": "external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "workspace_external_id": {
+          "name": "workspace_external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "container_id": {
+          "name": "container_id",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "client_id": {
+          "name": "client_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": false
+        },
+        "client_secret": {
+          "name": "client_secret",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": false
+        },
+        "oauth_scopes": {
+          "name": "oauth_scopes",
+          "type": "text[]",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "ARRAY[]::text[]"
+        },
+        "app_type": {
+          "name": "app_type",
+          "type": "app_type",
+          "typeSchema": "public",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "created_at": {
+          "name": "created_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        },
+        "updated_at": {
+          "name": "updated_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        }
+      },
+      "indexes": {},
+      "foreignKeys": {
+        "oauth_providers_workspace_id_workspaces_id_fk": {
+          "name": "oauth_providers_workspace_id_workspaces_id_fk",
+          "tableFrom": "oauth_providers",
+          "tableTo": "workspaces",
+          "columnsFrom": [
+            "workspace_id"
+          ],
+          "columnsTo": [
+            "id"
+          ],
+          "onDelete": "no action",
+          "onUpdate": "no action"
+        },
+        "oauth_providers_user_id_users_id_fk": {
+          "name": "oauth_providers_user_id_users_id_fk",
+          "tableFrom": "oauth_providers",
+          "tableTo": "users",
+          "columnsFrom": [
+            "user_id"
+          ],
+          "columnsTo": [
+            "id"
+          ],
+          "onDelete": "no action",
+          "onUpdate": "no action"
+        },
+        "oauth_providers_container_id_connectors_id_fk": {
+          "name": "oauth_providers_container_id_connectors_id_fk",
+          "tableFrom": "oauth_providers",
+          "tableTo": "connectors",
+          "columnsFrom": [
+            "container_id"
+          ],
+          "columnsTo": [
+            "id"
+          ],
+          "onDelete": "no action",
+          "onUpdate": "no action"
+        }
+      },
+      "compositePrimaryKeys": {},
+      "uniqueConstraints": {
+        "oauth_providers_external_id_unique": {
+          "name": "oauth_providers_external_id_unique",
+          "nullsNotDistinct": false,
+          "columns": [
+            "external_id"
+          ]
+        }
+      }
+    },
+    "public.sync_history": {
+      "name": "sync_history",
+      "schema": "",
+      "columns": {
+        "id": {
+          "name": "id",
+          "type": "serial",
+          "primaryKey": true,
+          "notNull": true
+        },
+        "workspace_id": {
+          "name": "workspace_id",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "external_id": {
+          "name": "external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "workspace_external_id": {
+          "name": "workspace_external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "data_added": {
+          "name": "data_added",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true,
+          "default": 0
+        },
+        "data_updated": {
+          "name": "data_updated",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true,
+          "default": 0
+        },
+        "data_deleted": {
+          "name": "data_deleted",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true,
+          "default": 0
+        },
+        "summary": {
+          "name": "summary",
+          "type": "jsonb",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "error_message": {
+          "name": "error_message",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": false,
+          "default": "''"
+        },
+        "type": {
+          "name": "type",
+          "type": "type",
+          "typeSchema": "public",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "status": {
+          "name": "status",
+          "type": "sync_status",
+          "typeSchema": "public",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "auth_type": {
+          "name": "auth_type",
+          "type": "auth_type",
+          "typeSchema": "public",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "app_type": {
+          "name": "app_type",
+          "type": "app_type",
+          "typeSchema": "public",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "config": {
+          "name": "config",
+          "type": "jsonb",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "last_ran_on": {
+          "name": "last_ran_on",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": false,
+          "default": "NOW()"
+        },
+        "created_at": {
+          "name": "created_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        },
+        "updated_at": {
+          "name": "updated_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        },
+        "deleted_at": {
+          "name": "deleted_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": false
+        }
+      },
+      "indexes": {},
+      "foreignKeys": {
+        "sync_history_workspace_id_workspaces_id_fk": {
+          "name": "sync_history_workspace_id_workspaces_id_fk",
+          "tableFrom": "sync_history",
+          "tableTo": "workspaces",
+          "columnsFrom": [
+            "workspace_id"
+          ],
+          "columnsTo": [
+            "id"
+          ],
+          "onDelete": "no action",
+          "onUpdate": "no action"
+        }
+      },
+      "compositePrimaryKeys": {},
+      "uniqueConstraints": {
+        "sync_history_external_id_unique": {
+          "name": "sync_history_external_id_unique",
+          "nullsNotDistinct": false,
+          "columns": [
+            "external_id"
+          ]
+        }
+      }
+    },
+    "public.sync_jobs": {
+      "name": "sync_jobs",
+      "schema": "",
+      "columns": {
+        "id": {
+          "name": "id",
+          "type": "serial",
+          "primaryKey": true,
+          "notNull": true
+        },
+        "workspace_id": {
+          "name": "workspace_id",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "external_id": {
+          "name": "external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "workspace_external_id": {
+          "name": "workspace_external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "email": {
+          "name": "email",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "connector_id": {
+          "name": "connector_id",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "type": {
+          "name": "type",
+          "type": "type",
+          "typeSchema": "public",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "status": {
+          "name": "status",
+          "type": "sync_status",
+          "typeSchema": "public",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "'NotStarted'"
+        },
+        "app_type": {
+          "name": "app_type",
+          "type": "app_type",
+          "typeSchema": "public",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "auth_type": {
+          "name": "auth_type",
+          "type": "auth_type",
+          "typeSchema": "public",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "config": {
+          "name": "config",
+          "type": "jsonb",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "last_ran_on": {
+          "name": "last_ran_on",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": false,
+          "default": "NOW()"
+        },
+        "created_at": {
+          "name": "created_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        },
+        "updated_at": {
+          "name": "updated_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        },
+        "deleted_at": {
+          "name": "deleted_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": false
+        }
+      },
+      "indexes": {},
+      "foreignKeys": {
+        "sync_jobs_workspace_id_workspaces_id_fk": {
+          "name": "sync_jobs_workspace_id_workspaces_id_fk",
+          "tableFrom": "sync_jobs",
+          "tableTo": "workspaces",
+          "columnsFrom": [
+            "workspace_id"
+          ],
+          "columnsTo": [
+            "id"
+          ],
+          "onDelete": "no action",
+          "onUpdate": "no action"
+        },
+        "sync_jobs_connector_id_connectors_id_fk": {
+          "name": "sync_jobs_connector_id_connectors_id_fk",
+          "tableFrom": "sync_jobs",
+          "tableTo": "connectors",
+          "columnsFrom": [
+            "connector_id"
+          ],
+          "columnsTo": [
+            "id"
+          ],
+          "onDelete": "no action",
+          "onUpdate": "no action"
+        }
+      },
+      "compositePrimaryKeys": {},
+      "uniqueConstraints": {
+        "sync_jobs_external_id_unique": {
+          "name": "sync_jobs_external_id_unique",
+          "nullsNotDistinct": false,
+          "columns": [
+            "external_id"
+          ]
+        }
+      }
+    },
+    "public.users": {
+      "name": "users",
+      "schema": "",
+      "columns": {
+        "id": {
+          "name": "id",
+          "type": "serial",
+          "primaryKey": true,
+          "notNull": true
+        },
+        "workspace_id": {
+          "name": "workspace_id",
+          "type": "integer",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "email": {
+          "name": "email",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "name": {
+          "name": "name",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "photoLink": {
+          "name": "photoLink",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": false
+        },
+        "external_id": {
+          "name": "external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "workspace_external_id": {
+          "name": "workspace_external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "created_at": {
+          "name": "created_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        },
+        "updated_at": {
+          "name": "updated_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        },
+        "deleted_at": {
+          "name": "deleted_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "'1970-01-01T00:00:00Z'"
+        },
+        "last_login": {
+          "name": "last_login",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": false
+        },
+        "role": {
+          "name": "role",
+          "type": "role",
+          "typeSchema": "public",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "'User'"
+        }
+      },
+      "indexes": {
+        "email_unique_index": {
+          "name": "email_unique_index",
+          "columns": [
+            {
+              "expression": "LOWER(\"email\")",
+              "asc": true,
+              "isExpression": true,
+              "nulls": "last"
+            }
+          ],
+          "isUnique": true,
+          "concurrently": false,
+          "method": "btree",
+          "with": {}
+        }
+      },
+      "foreignKeys": {
+        "users_workspace_id_workspaces_id_fk": {
+          "name": "users_workspace_id_workspaces_id_fk",
+          "tableFrom": "users",
+          "tableTo": "workspaces",
+          "columnsFrom": [
+            "workspace_id"
+          ],
+          "columnsTo": [
+            "id"
+          ],
+          "onDelete": "no action",
+          "onUpdate": "no action"
+        }
+      },
+      "compositePrimaryKeys": {},
+      "uniqueConstraints": {
+        "users_external_id_unique": {
+          "name": "users_external_id_unique",
+          "nullsNotDistinct": false,
+          "columns": [
+            "external_id"
+          ]
+        }
+      }
+    },
+    "public.workspaces": {
+      "name": "workspaces",
+      "schema": "",
+      "columns": {
+        "id": {
+          "name": "id",
+          "type": "serial",
+          "primaryKey": true,
+          "notNull": true
+        },
+        "name": {
+          "name": "name",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "domain": {
+          "name": "domain",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "created_by": {
+          "name": "created_by",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "external_id": {
+          "name": "external_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "photoLink": {
+          "name": "photoLink",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": false
+        },
+        "created_at": {
+          "name": "created_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        },
+        "updated_at": {
+          "name": "updated_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "NOW()"
+        },
+        "deleted_at": {
+          "name": "deleted_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": false
+        }
+      },
+      "indexes": {},
+      "foreignKeys": {},
+      "compositePrimaryKeys": {},
+      "uniqueConstraints": {
+        "workspaces_domain_unique": {
+          "name": "workspaces_domain_unique",
+          "nullsNotDistinct": false,
+          "columns": [
+            "domain"
+          ]
+        },
+        "workspaces_created_by_unique": {
+          "name": "workspaces_created_by_unique",
+          "nullsNotDistinct": false,
+          "columns": [
+            "created_by"
+          ]
+        },
+        "workspaces_external_id_unique": {
+          "name": "workspaces_external_id_unique",
+          "nullsNotDistinct": false,
+          "columns": [
+            "external_id"
+          ]
+        }
+      }
+    }
+  },
+  "enums": {
+    "public.app_type": {
+      "name": "app_type",
+      "schema": "public",
+      "values": [
+        "google-workspace",
+        "google-drive",
+        "gmail",
+        "notion",
+        "google-calendar"
+      ]
+    },
+    "public.auth_type": {
+      "name": "auth_type",
+      "schema": "public",
+      "values": [
+        "oauth",
+        "service_account",
+        "custom",
+        "api_key"
+      ]
+    },
+    "public.connector_type": {
+      "name": "connector_type",
+      "schema": "public",
+      "values": [
+        "SaaS",
+        "Database",
+        "Api",
+        "File",
+        "Website"
+      ]
+    },
+    "public.message_role": {
+      "name": "message_role",
+      "schema": "public",
+      "values": [
+        "system",
+        "user",
+        "assistant"
+      ]
+    },
+    "public.status": {
+      "name": "status",
+      "schema": "public",
+      "values": [
+        "connected",
+        "connecting",
+        "failed",
+        "not-connected"
+      ]
+    },
+    "public.type": {
+      "name": "type",
+      "schema": "public",
+      "values": [
+        "ChangeToken",
+        "Partial",
+        "FullSync"
+      ]
+    },
+    "public.sync_status": {
+      "name": "sync_status",
+      "schema": "public",
+      "values": [
+        "NotStarted",
+        "Started",
+        "Failed",
+        "Successful"
+      ]
+    },
+    "public.role": {
+      "name": "role",
+      "schema": "public",
+      "values": [
+        "User",
+        "TeamLeader",
+        "Admin",
+        "SuperAdmin"
+      ]
+    }
+  },
+  "schemas": {},
+  "sequences": {},
+  "_meta": {
+    "columns": {},
+    "schemas": {},
+    "tables": {}
+  }
+}
\ No newline at end of file
diff --git a/server/migrations/meta/_journal.json b/server/migrations/meta/_journal.json
index aea59411..66e2360b 100644
--- a/server/migrations/meta/_journal.json
+++ b/server/migrations/meta/_journal.json
@@ -8,6 +8,13 @@
       "when": 1736661636928,
       "tag": "0000_early_warlock",
       "breakpoints": true
+    },
+    {
+      "idx": 1,
+      "version": "7",
+      "when": 1737276650384,
+      "tag": "0001_dark_maddog",
+      "breakpoints": true
     }
   ]
 }
\ No newline at end of file
diff --git a/server/search/types.ts b/server/search/types.ts
index 69d71248..5c0c7d89 100644
--- a/server/search/types.ts
+++ b/server/search/types.ts
@@ -5,6 +5,8 @@ export const mailSchema = "mail"
 export const eventSchema = "event"
 export const userQuerySchema = "user_query"
 export const mailAttachmentSchema = "mail_attachment"
+export const chatAttachmentSchema = "chatAttachment"
+
 export type VespaSchema =
   | typeof fileSchema
   | typeof userSchema
@@ -39,6 +41,7 @@ const Schemas = z.union([
   z.literal(eventSchema),
   z.literal(userQuerySchema),
   z.literal(mailAttachmentSchema),
+  z.literal(chatAttachmentSchema),
 ])
 
 export enum MailEntity {
@@ -280,6 +283,18 @@ export const VespaEventSchema = z.object({
   defaultStartTime: z.boolean(),
 })
 
+export const VespaChatAttachmentSchema = z.object({
+  docId: z.string(),
+  title: z.string(),
+  chunks: z.array(z.string()),
+  ownerEmail: z.string().nullable(),
+  mimeType: z.string().nullable(),
+  createdAt: z.number(),
+  updatedAt: z.number(),
+  chatId: z.string(),
+  messageId: z.string(),
+})
+
 export const VespaMailSearchSchema = VespaMailSchema.extend({
   sddocname: z.literal("mail"),
 })
@@ -314,6 +329,17 @@ export const VespaUserQueryHGetSchema = VespaUserQueryHistorySchema.extend({
   sddocname: z.literal("user_query"),
 }).merge(defaultVespaFieldsSchema)
 
+export const VespaChatAttachmentSearchSchema = VespaChatAttachmentSchema.extend(
+  {
+    sddocname: z.literal(chatAttachmentSchema),
+  },
+)
+  .merge(defaultVespaFieldsSchema)
+  .extend({
+    chunks_summary: z.array(z.string()),
+  })
+
+
 export const VespaMailGetSchema = VespaMailSchema.merge(
   defaultVespaFieldsSchema,
 )
@@ -329,6 +355,7 @@ export const VespaSearchFieldsUnionSchema = z.discriminatedUnion("sddocname", [
   VespaEventSearchSchema,
   VespaUserQueryHGetSchema,
   VespaMailAttachmentSearchSchema,
+  VespaChatAttachmentSearchSchema,
 ])
 
 // Match features for file schema
@@ -364,12 +391,19 @@ const MailAttachmentMatchFeaturesSchema = z.object({
   scaled_bm25_filename: z.number().optional(),
 })
 
+const ChatAttachmentFeaturesSchema = z.object({
+  "bm25(title)": z.number().optional(),
+  "bm25(chunks)": z.number().optional(),
+  "closeness(field, chunk_embeddings)": z.number().optional(),
+})
+
 const SearchMatchFeaturesSchema = z.union([
   FileMatchFeaturesSchema,
   UserMatchFeaturesSchema,
   MailMatchFeaturesSchema,
   EventMatchFeaturesSchema,
   MailAttachmentMatchFeaturesSchema,
+  ChatAttachmentFeaturesSchema,
 ])
 const VespaSearchFieldsSchema = z
   .object({
@@ -470,6 +504,9 @@ export type VespaSearchResponse = z.infer<typeof VespaSearchResponseSchema>
 
 export type VespaFileGet = z.infer<typeof VespaFileGetSchema>
 export type VespaFileSearch = z.infer<typeof VespaFileSearchSchema>
+export type VespaChatAttachmentSearch = z.infer<
+  typeof VespaChatAttachmentSearchSchema
+>
 export type VespaMailSearch = z.infer<typeof VespaMailSearchSchema>
 export type VespaMailAttachmentSearch = z.infer<
   typeof VespaMailAttachmentSearchSchema
@@ -613,6 +650,8 @@ export type VespaMailAttachment = z.infer<typeof VespaMailAttachmentSchema>
 
 export type VespaEvent = z.infer<typeof VespaEventSchema>
 
+export type VespaChatAttachment = z.infer<typeof VespaChatAttachmentSchema>
+
 export const MailResponseSchema = VespaMailGetSchema.pick({
   docId: true,
   threadId: true,
diff --git a/server/search/vespa.ts b/server/search/vespa.ts
index bcee2a22..651ac141 100644
--- a/server/search/vespa.ts
+++ b/server/search/vespa.ts
@@ -2,6 +2,7 @@ import {
   Apps,
   CalendarEntity,
   DriveEntity,
+  chatAttachmentSchema,
   eventSchema,
   MailEntity,
   fileSchema,
@@ -23,6 +24,7 @@ import type {
   VespaUserQueryHistory,
   VespaSchema,
   VespaMailAttachment,
+  VespaChatAttachment,
 } from "@/search/types"
 import { getErrorMessage } from "@/utils"
 import config from "@/config"
@@ -88,7 +90,8 @@ export const insert = async (
     | VespaMail
     | VespaEvent
     | VespaUserQueryHistory
-    | VespaMailAttachment,
+    | VespaMailAttachment
+    | VespaChatAttachment,
   schema: VespaSchema,
 ) => {
   try {
@@ -143,6 +146,7 @@ const AllSources = [
   mailSchema,
   eventSchema,
   mailAttachmentSchema,
+  chatAttachmentSchema,
 ].join(", ")
 
 export const autocomplete = async (
@@ -450,6 +454,49 @@ export const searchVespa = async (
   }
 }
 
+export const searchVespaWithChatAttachment = async (
+  query: string,
+  email: string,
+  chatId: string,
+  limit = config.page,
+  offset?: number,
+): Promise<VespaSearchResponse> => {
+  const url = `${vespaEndpoint}/search/`
+
+  let yql = `select * from sources ${chatAttachmentSchema}
+        where (
+            (
+              ({targetHits:${limit}}userInput(@query))
+              or
+              ({targetHits:${limit}}nearestNeighbor(chunk_embeddings, e))
+            )
+            and chatId contains "${chatId}")`
+
+  const hybridDefaultPayload = {
+    yql,
+    query,
+    email,
+    "ranking.profile": "default",
+    "input.query(e)": "embed(@query)",
+    hits: limit,
+    alpha: 0.5,
+    ...(offset
+      ? {
+          offset,
+        }
+      : {}),
+    ...(chatId ? { chatId } : {}),
+  }
+  try {
+    return await vespa.search<VespaSearchResponse>(hybridDefaultPayload)
+  } catch (error) {
+    throw new ErrorPerformingSearch({
+      cause: error as Error,
+      sources: chatAttachmentSchema,
+    })
+  }
+}
+
 /**
  * Retrieves the total count of documents in the specified schema, namespace, and cluster.
  */
@@ -520,6 +567,55 @@ export const UpdateEventCancelledInstances = async (
   }
 }
 
+export const AddChatMessageIdToAttachment = async (
+  schema: string,
+  docId: string,
+  chatId: string,
+  messageId: string,
+) => {
+  const url = `${vespaEndpoint}/document/v1/${NAMESPACE}/${schema}/docid/${docId}`
+  try {
+    const response = await fetch(url, {
+      method: "PUT",
+      headers: {
+        "Content-Type": "application/json",
+      },
+      body: JSON.stringify({
+        fields: {
+          chatId: { assign: chatId },
+          messageId: { assign: messageId },
+        },
+      }),
+    })
+
+    if (!response.ok) {
+      const errorText = response.statusText
+      throw new ErrorUpdatingDocument({
+        message: `Failed to add chatId and messageId to chatAttachment: ${response.status} ${response.statusText} - ${errorText}`,
+        docId,
+        sources: schema,
+      })
+    }
+
+    const data = await response.json()
+
+    Logger.info(
+      `Successfully added chatId and messageId to chatAttachment for document ${docId}.`,
+    )
+  } catch (error) {
+    const errMessage = getErrorMessage(error)
+    Logger.error(
+      `Error adding chatId and messageId for document ${docId}:`,
+      errMessage,
+    )
+    throw new ErrorUpdatingDocument({
+      docId,
+      cause: error as Error,
+      sources: schema,
+    })
+  }
+}
+
 export const UpdateDocument = async (
   schema: VespaSchema,
   docId: string,
diff --git a/server/search/vespaClient.ts b/server/search/vespaClient.ts
index 9ab831c6..0cd7f263 100644
--- a/server/search/vespaClient.ts
+++ b/server/search/vespaClient.ts
@@ -12,6 +12,7 @@ import type {
   VespaUserQueryHistory,
   VespaSchema,
   VespaMailAttachment,
+  VespaChatAttachment,
 } from "@/search/types"
 import { getErrorMessage } from "@/utils"
 import type { AppEntityCounts } from "@/search/vespa"
@@ -172,7 +173,8 @@ class VespaClient {
       | VespaMail
       | VespaEvent
       | VespaUserQueryHistory
-      | VespaMailAttachment,
+      | VespaMailAttachment
+      | VespaChatAttachment,
     options: VespaConfigValues,
   ): Promise<void> {
     try {
diff --git a/server/server.ts b/server/server.ts
index ce4d0970..91a9ea9a 100644
--- a/server/server.ts
+++ b/server/server.ts
@@ -8,6 +8,7 @@ import {
   chatHistorySchema,
   chatRenameSchema,
   chatSchema,
+  fileUploadSchema,
   messageRetrySchema,
   messageSchema,
   SearchApi,
@@ -55,6 +56,7 @@ import {
   GetChatApi,
   MessageApi,
   MessageRetryApi,
+  UploadFilesApi,
 } from "./api/chat"
 import { z } from "zod"
 import { UserRole } from "./shared/types"
@@ -161,6 +163,7 @@ export const AppRoutes = app
     zValidator("query", messageRetrySchema),
     MessageRetryApi,
   )
+  .post("/chat/upload", zValidator("form", fileUploadSchema), UploadFilesApi)
   .get("/search", zValidator("query", searchSchema), SearchApi)
   .get("/me", GetUserWorkspaceInfo)
   .get("/proxy/:url", ProxyUrl)
diff --git a/server/shared/types.ts b/server/shared/types.ts
index eeb340dd..f49ff7ed 100644
--- a/server/shared/types.ts
+++ b/server/shared/types.ts
@@ -30,7 +30,7 @@ import { z } from "zod"
 // @ts-ignore
 export type { MessageReqType } from "@/api/search"
 // @ts-ignore
-export type { Citation } from "@/api/chat"
+export type { Citation, AttachmentMetadata } from "@/api/chat"
 export type {
   SelectPublicMessage,
   PublicUser,
diff --git a/server/vespa/schemas/chatAttachment.sd b/server/vespa/schemas/chatAttachment.sd
new file mode 100644
index 00000000..29c63a34
--- /dev/null
+++ b/server/vespa/schemas/chatAttachment.sd
@@ -0,0 +1,151 @@
+schema chatAttachment {
+  document chatAttachment {
+    field docId type string {
+      indexing: attribute | summary
+    }
+    
+    field title type string {
+      indexing: index | summary | attribute
+      index {
+        enable-bm25
+      }
+    }
+
+    field chunks type array<string> {
+      indexing: index | summary
+      index: enable-bm25
+    }
+
+    field ownerEmail type string {
+      indexing: attribute | summary
+    }
+
+    field mimeType type string {
+      indexing: attribute | summary
+    }
+
+    field createdAt type long {
+      indexing: attribute | summary
+      attribute: fast-search
+    }
+
+    field updatedAt type long {
+      indexing: attribute | summary
+      attribute: fast-search
+    }
+
+    field chatId type string {
+      indexing: attribute | summary
+      attribute: fast-search
+      match: exact
+    }
+    
+    field messageId type string {
+      indexing: attribute | summary
+      attribute: fast-search
+      match: exact
+    }
+  }
+
+  field chunk_embeddings type tensor<bfloat16>(p{}, v[384])  {
+    indexing: input chunks | embed | attribute | index
+    attribute {
+        distance-metric: angular
+    }
+  }
+  
+  fieldset default {
+    fields: title, chunks
+  }
+
+  # Hybrid search rank profile combining BM25 for title and chunks, and vector search for chunk embeddings
+  rank-profile initial {
+    # Inputs for the query vector and alpha for hybrid search
+    inputs {
+      query(e) tensor<bfloat16>(v[384])  # Query embedding
+      query(alpha) double  # Alpha parameter for hybrid weight
+    }
+
+    # Compute vector similarity for chunks
+    function chunk_vector_score() {
+      expression: closeness(field, chunk_embeddings)
+    }
+
+    # Compute BM25 score for title
+    function title_bm25_score() {
+      expression: bm25(title)
+    }
+
+    # First phase combines BM25 (title and chunks) and vector similarity (chunks)
+    first-phase {
+      expression: (query(alpha) * chunk_vector_score) + ((1 - query(alpha)) * (bm25(chunks) +bm25(title)))
+    }
+
+    # Global phase (optional if more complex reranking is needed)
+    global-phase {
+      expression {
+        (
+          (query(alpha) * normalize_linear(chunk_vector_score)) +
+          ((1 - query(alpha)) * (normalize_linear(bm25(chunks)) + normalize_linear(bm25(title))))
+        )
+      }
+      rerank-count: 1000
+    }
+
+    match-features {
+      bm25(title)
+      bm25(chunks)
+      closeness(field, chunk_embeddings)
+    }
+  }
+
+  rank-profile default inherits initial {
+    function chunk_vector_score() {
+      expression: closeness(field, chunk_embeddings)
+    }
+
+    function scale(val) {
+      expression: 2*atan(val/4)/(3.14159)
+    }
+
+    function scaled_bm25_chunks() {
+      expression: scale(bm25(chunks))
+    }
+
+    function scaled_bm25_title() {
+      expression: scale(bm25(title))
+    }
+
+    function combined_bm25() {
+      expression: 0.3*scaled_bm25_chunks + 0.8*scaled_bm25_title
+    }
+
+    # First phase combines BM25 (title and chunks) and vector similarity (chunks)
+    first-phase {
+      expression: (0.5 * chunk_vector_score) + combined_bm25
+    }
+
+    global-phase {
+      expression {
+        (
+          (0.5 * normalize_linear(chunk_vector_score)) +
+          (max(scaled_bm25_title,scaled_bm25_chunks))
+        )
+      }
+      rerank-count: 1000
+    }
+
+    match-features {
+      chunk_vector_score
+      scaled_bm25_chunks
+      scaled_bm25_title
+    }
+  }
+
+  document-summary default {
+    summary chunks_summary {
+      bolding: on
+      source: chunks
+    }
+  }
+}
\ No newline at end of file
diff --git a/server/vespa/services.xml b/server/vespa/services.xml
index a6f9113f..d69640a1 100644
--- a/server/vespa/services.xml
+++ b/server/vespa/services.xml
@@ -24,6 +24,7 @@
             <document type="mail_attachment" mode="index" />
             <document type="user_query" mode="index" />
             <document type="event" mode="index" />
+            <document type="chatAttachment" mode="index" />
         </documents>
         <nodes>
             <node distribution-key="0" hostalias="node1" />