diff --git a/azure-pipelines-insertion.yml b/azure-pipelines-insertion.yml
index de80c5c19f..ad6d8647ba 100644
--- a/azure-pipelines-insertion.yml
+++ b/azure-pipelines-insertion.yml
@@ -1,6 +1,6 @@
 parameters:
   - name: 'ComponentBranchName'
-    default: 'rel/18.7'
+    default: 'main'
   - name: 'CreateDraftPR'
     default: 'false'
   - name: 'OptionalTitlePrefix'
@@ -44,7 +44,7 @@ schedules:
     displayName: Daily midnight insertion to VS
     branches:
       include:
-      - rel/18.7
+      - main
     always: true
 
 resources:
@@ -96,12 +96,16 @@ extends:
                     & eng/common/dotnet-install.ps1 -version $version -runtime ''
 
               - task: AzureCLI@2
-                displayName: 'Run VS Insertion'
+                displayName: '🚀 Run VS Insertion'
                 inputs:
                   azureSubscription: 'DncEng Insertion: Roslyn and Razor'
                   scriptType: pscore
                   scriptLocation: inlineScript
                   inlineScript: |
+                    # Disable .NET first-time experience to avoid delays
+                    $env:DOTNET_NOLOGO = '1'
+                    $env:DOTNET_SKIP_FIRST_TIME_EXPERIENCE = '1'
+
                     # Install Roslyn insertion tools from the dnceng feed, using --tool-path as a workaround to avoid resetting the process to pick up dotnet tool path changes
                     $dotnet = "$(Build.SourcesDirectory)\.dotnet\dotnet.exe"
                     & $dotnet tool install Microsoft.RoslynTools --prerelease --add-source https://pkgs.dev.azure.com/dnceng/public/_packaging/dotnet-eng/nuget/v3/index.json --tool-path .
@@ -153,8 +157,99 @@ extends:
                     }
 
                     "Running: ./roslyn-tools.exe $($insertArgs -join ' ')"
-                    ./roslyn-tools.exe @insertArgs
+                    $roslynOutput = ./roslyn-tools.exe @insertArgs 2>&1 | ForEach-Object { Write-Host $_; $_ }
                     if ($LASTEXITCODE -ne 0) {
                       exit $LASTEXITCODE
                     }
 
+                    # Push vstest.console app.config to the insertion PR branch in the VS repo.
+                    # The file maps to src/vset/Agile/TestPlatform/RocksteadyCLI/App.config in VS.
+                    $devdivToken = "$(dn-bot-devdiv-build-e-code-full-release-e-packaging-r)"
+                    $base64Token = [Convert]::ToBase64String([Text.Encoding]::ASCII.GetBytes(":$devdivToken"))
+                    $headers = @{
+                      Authorization = "Basic $base64Token"
+                      'Content-Type' = 'application/json'
+                    }
+
+                    $devdivOrg = "https://dev.azure.com/devdiv"
+                    $project = "DevDiv"
+                    $vsRepoId = "a290117c-5a8a-40f7-bc2c-f14dbe3acf6d"
+                    $targetFilePath = "/src/vset/Agile/TestPlatform/RocksteadyCLI/App.config"
+
+                    # Extract the PR number from roslyn-tools output.
+                    # The tool logs a PR URL like: https://dev.azure.com/devdiv/DevDiv/_git/VS/pullrequest/735439
+                    # We match the URL pattern specifically to avoid grabbing timestamps from PR titles.
+                    $outputText = $roslynOutput -join "`n"
+                    $prId = $null
+                    if ($outputText -match '/pullrequest/(\d+)') {
+                      $prId = $Matches[1]
+                    } elseif ($outputText -match 'pullrequests/(\d+)') {
+                      $prId = $Matches[1]
+                    }
+
+                    if (-not $prId) {
+                      Write-Error "Could not extract PR ID from roslyn-tools output. Cannot push App.config."
+                      Write-Host "roslyn-tools output was:"
+                      Write-Host $outputText
+                      exit 1
+                    }
+                    else {
+                      Write-Host "Detected insertion PR #$prId, pushing App.config..."
+
+                      try {
+                        # Get the PR to find its source branch
+                        $prUrl = "$devdivOrg/$project/_apis/git/repositories/$vsRepoId/pullrequests/${prId}?api-version=7.1"
+                        $pr = Invoke-RestMethod -Uri $prUrl -Headers $headers -Method Get
+                        $sourceBranch = $pr.sourceRefName
+                        Write-Host "PR source branch: $sourceBranch"
+
+                        # Get the latest commit on the insertion branch
+                        $refFilter = ($sourceBranch -replace '^refs/', '')
+                        $encodedFilter = [Uri]::EscapeDataString($refFilter)
+                        $refUrl = "$devdivOrg/$project/_apis/git/repositories/$vsRepoId/refs?filter=$encodedFilter&api-version=7.1"
+                        $refResponse = Invoke-RestMethod -Uri $refUrl -Headers $headers -Method Get
+                        if (-not $refResponse.value -or $refResponse.value.Count -eq 0) {
+                          throw "Could not resolve ref for branch $sourceBranch"
+                        }
+                        $latestCommitId = $refResponse.value[0].objectId
+
+                        # Read the app.config from the vstest checkout
+                        $appConfigContent = Get-Content -Raw -Path "$(Build.SourcesDirectory)/src/vstest.console/app.config"
+
+                        # Push the app.config to the insertion branch
+                        $pushUrl = "$devdivOrg/$project/_apis/git/repositories/$vsRepoId/pushes?api-version=7.1"
+                        $pushBody = @{
+                          refUpdates = @(
+                            @{
+                              name = $sourceBranch
+                              oldObjectId = $latestCommitId
+                            }
+                          )
+                          commits = @(
+                            @{
+                              comment = "Update RocksteadyCLI App.config from vstest"
+                              changes = @(
+                                @{
+                                  changeType = "edit"
+                                  item = @{
+                                    path = $targetFilePath
+                                  }
+                                  newContent = @{
+                                    content = $appConfigContent
+                                    contentType = "rawtext"
+                                  }
+                                }
+                              )
+                            }
+                          )
+                        } | ConvertTo-Json -Depth 10
+
+                        $pushResponse = Invoke-RestMethod -Uri $pushUrl -Headers $headers -Method Post -Body $pushBody
+                        Write-Host "Pushed App.config to insertion branch. Commit: $($pushResponse.commits[0].commitId)"
+                      }
+                      catch {
+                        Write-Error "Failed to push App.config to insertion branch: $_"
+                        exit 1
+                      }
+                    }
+