diff --git a/locales/en/out/constants.i18n.json b/locales/en/out/constants.i18n.json
index 7ac3a0b1c..06967abcc 100644
--- a/locales/en/out/constants.i18n.json
+++ b/locales/en/out/constants.i18n.json
@@ -4,7 +4,8 @@
   "dialogResponses.help": "I need help",
   "dialogResponses.tutorials": "Tutorials on Adafruit",
   "error.noDevice": "No plugged in boards detected. Please double check if your board is connected and/or properly formatted",
-  "error.stderr": "[ERROR] {0} \n",
+  "error.noFileToRun": "\n[ERROR] We can't find the .py file to run on simulator. Open up a new .py file, or browse through some examples",
+  "error.stderr": "\n[ERROR] {0} \n",
   "error.unexpectedMessage": "Webview sent an unexpected message",
   "info.deployDevice": "\n[INFO] Deploying code to the device...\n",
   "info.deploySimulator": "\n[INFO] Deploying code to the simulator...\n",
diff --git a/src/constants.ts b/src/constants.ts
index 38f30280a..78b3021bb 100644
--- a/src/constants.ts
+++ b/src/constants.ts
@@ -14,8 +14,12 @@ export const CONSTANTS = {
       "error.noDevice",
       "No plugged in boards detected. Please double check if your board is connected and/or properly formatted"
     ),
+    NO_FILE_TO_RUN: localize(
+      "error.noFileToRun",
+      "\n[ERROR] We can't find the .py file to run. Open up a new .py file, or browse through some examples to start with: https://github.com/adafruit/Adafruit_CircuitPython_CircuitPlayground/tree/master/examples"
+    ),
     STDERR: (data: string) => {
-      return localize("error.stderr", `[ERROR] ${data} \n`);
+      return localize("error.stderr", `\n[ERROR] ${data} \n`);
     },
     UNEXPECTED_MESSAGE: localize(
       "error.unexpectedMessage",
@@ -101,17 +105,17 @@ export enum TelemetryEventName {
 export enum WebviewMessages {
   BUTTON_PRESS = "button-press",
   PLAY_SIMULATOR = "play-simulator"
-} 
+}
 
 
 // tslint:disable-next-line: no-namespace
 export namespace DialogResponses {
   export const HELP: MessageItem = {
     title: localize("dialogResponses.help", "I need help")
-  }; 
+  };
   export const DONT_SHOW: MessageItem = {
     title: localize("dialogResponses.dontShowAgain", "Don't Show Again")
-  }; 
+  };
   export const TUTORIALS: MessageItem = {
     title: localize("dialogResponses.tutorials", "Tutorials on Adafruit")
   };
diff --git a/src/extension.ts b/src/extension.ts
index 61785b09a..9ada825c7 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -9,6 +9,7 @@ import * as open from "open";
 import TelemetryAI from "./telemetry/telemetryAI";
 import { CONSTANTS, DialogResponses, TelemetryEventName, WebviewMessages } from "./constants";
 
+let currentFileAbsPath: string = "";
 // Notification booleans
 let firstTimeClosed: boolean = true;
 let shouldShowNewProject: boolean = true;
@@ -188,16 +189,16 @@ export function activate(context: vscode.ExtensionContext) {
       return;
     }
 
-    TelemetryAI.trackFeatureUsage(TelemetryEventName.COMMAND_RUN_SIMULATOR);
-
     console.info(CONSTANTS.INFO.RUNNING_CODE);
     const activeTextEditor: vscode.TextEditor | undefined =
       vscode.window.activeTextEditor;
-    let currentFileAbsPath: string = "";
 
-    if (activeTextEditor) {
-      currentFileAbsPath = activeTextEditor.document.fileName;
-    }
+    updateCurrentFileIfPython(activeTextEditor);
+
+    TelemetryAI.trackFeatureUsage(TelemetryEventName.COMMAND_RUN_SIMULATOR);
+
+
+    if (currentFileAbsPath === "") { logToOutputChannel(outChannel, CONSTANTS.ERROR.NO_FILE_TO_RUN, true); }
 
     // Get the Python script path (And the special URI to use with the webview)
     const onDiskPath = vscode.Uri.file(
@@ -286,11 +287,10 @@ export function activate(context: vscode.ExtensionContext) {
 
     const activeTextEditor: vscode.TextEditor | undefined =
       vscode.window.activeTextEditor;
-    let currentFileAbsPath: string = "";
 
-    if (activeTextEditor) {
-      currentFileAbsPath = activeTextEditor.document.fileName;
-    }
+    updateCurrentFileIfPython(activeTextEditor);
+
+    if (currentFileAbsPath === "") { logToOutputChannel(outChannel, CONSTANTS.ERROR.NO_FILE_TO_RUN, true); }
 
     // Get the Python script path (And the special URI to use with the webview)
     const onDiskPath = vscode.Uri.file(
@@ -370,6 +370,12 @@ export function activate(context: vscode.ExtensionContext) {
   );
 }
 
+const updateCurrentFileIfPython = (activeTextEditor: vscode.TextEditor | undefined) => {
+  if (activeTextEditor && activeTextEditor.document.languageId === "python") {
+    currentFileAbsPath = activeTextEditor.document.fileName;
+  }
+}
+
 const handleButtonPressTelemetry = (buttonState: any) => {
   if (buttonState["button_a"] && buttonState["button_b"]) {
     TelemetryAI.trackFeatureUsage(TelemetryEventName.SIMULATOR_BUTTON_AB);