diff --git a/azure-pipelines/vs-insertion.yml b/azure-pipelines/vs-insertion.yml
index 7e1a27f3ed7..16de6ced0f1 100644
--- a/azure-pipelines/vs-insertion.yml
+++ b/azure-pipelines/vs-insertion.yml
@@ -1,32 +1,46 @@
-# Create a VS insertion (DotNet-MSBuild-Trusted -> VS) from a build artifact on main or any servicing branch. 
+# Create a VS insertion (DotNet-MSBuild-Trusted -> VS) from a CI run on main or any servicing branch.
+# To achieve insertion automation, this pipeline definition yml has to be on servicing branches and main.
+
+
+# Runs in 3 modes: 
+# 1. daily main insertion from latest main CI.
+#   - can be disabled in the UI by adding a custom schedule for any branch. 
+# 2. trigger insert as a followup to a servicing CI run.
+#   - can be disabled in the UI by adding a custom CI trigger.
+# 3. manual insertion - select manually the TargetBranch and inserted CI run.
 trigger: none
+pr: none
 name: $(Date:yyyyMMdd).$(Rev:r)
 
+schedules:
+  - cron: '0 3 * * 1-5' # Runs every weekday at 3AM UTC
+    displayName: Daily VS insertion main
+    branches:
+      include:
+        - main
+    always: false # Don't run if there are no code changes
+
 resources:
   pipelines:
   - pipeline: 'MSBuild'
     project: 'DevDiv'
     source: 'MSBuild'
+    branch: main # for daily main scheduled insertion
+    trigger:
+      branches:
+        include: # trigger as a followup to servicing CI
+          - vs*
   repositories:
   - repository: 1ESPipelineTemplates
     type: git
     name: 1ESPipelineTemplates/1ESPipelineTemplates
     ref: refs/tags/release
 
-schedules:
-  - cron: '0 3 * * *'   # Runs every day at 3AM UTC
-    displayName: Daily VS insertion
-    branches:
-      include:
-        - main
-        - vs*
-    always: false # Don't run if there are no code changes
-
 parameters:
   - name: TargetBranch
     default: auto
     type: string
-    displayName: 'Insertion Target Branch (recommended to use `auto`)'
+    displayName: 'Insertion Target Branch (select for manual insertion)'
     values:
       - auto
       - main
@@ -88,6 +102,11 @@ variables:
     value: '$(ArtifactPackagesPath)/Microsoft.NET.StringTools*.nupkg'
   - name: ExternalAPIsPackagePattern
     value: '$(ArtifactPackagesPath)/VS.ExternalAPIs.*.nupkg'
+  # servicing branches until 17.12 also include Microsoft.Build.Engine and Microsoft.Build.Conversion.Core
+  - name: EngineIncludedProps
+    value: VS.ExternalAPIs.MSBuild=$(MSBuild_ExtApisPackageVersion);Microsoft.Build=$(MicrosoftNETStringToolsPackageVersion);Microsoft.Build.Conversion.Core=$(MicrosoftNETStringToolsPackageVersion);Microsoft.Build.Engine=$(MicrosoftNETStringToolsPackageVersion);Microsoft.Build.Framework=$(MicrosoftNETStringToolsPackageVersion);Microsoft.Build.Tasks.Core=$(MicrosoftNETStringToolsPackageVersion);Microsoft.Build.Utilities.Core=$(MicrosoftNETStringToolsPackageVersion);Microsoft.NET.StringTools=$(MicrosoftNETStringToolsPackageVersion)
+  - name: NoEngineProps
+    value: VS.ExternalAPIs.MSBuild=$(MSBuild_ExtApisPackageVersion);Microsoft.Build=$(MicrosoftNETStringToolsPackageVersion);Microsoft.Build.Framework=$(MicrosoftNETStringToolsPackageVersion);Microsoft.Build.Tasks.Core=$(MicrosoftNETStringToolsPackageVersion);Microsoft.Build.Utilities.Core=$(MicrosoftNETStringToolsPackageVersion);Microsoft.NET.StringTools=$(MicrosoftNETStringToolsPackageVersion)
 
 extends:
   template: v1/1ES.Official.PipelineTemplate.yml@1ESPipelineTemplates
@@ -186,6 +205,14 @@ extends:
               $packageVersion = $packageFile.BaseName.TrimStart("Microsoft.NET.StringTools")
               Write-Host "Setting MicrosoftNETStringToolsPackageVersion to '$packageVersion'"
               Write-Host "##vso[task.setvariable variable=MicrosoftNETStringToolsPackageVersion]$($packageVersion)"
+              if ("$(InsertTargetBranch)" -in @("vs17.0", "vs17.3", "vs17.6", "vs17.8", "vs17.10", "vs17.11", "vs17.12"))
+              {
+                  Write-Host "##vso[task.setvariable variable=InsertPackagePropsValues]$($EngineIncludedProps)"
+              }
+              else
+              {
+                  Write-Host "##vso[task.setvariable variable=InsertPackagePropsValues]$($NoEngineProps)"
+              }
         - task: 1ES.PublishNuGet@1
           displayName: 'Push MSBuild CoreXT packages'
           inputs:
@@ -221,11 +248,7 @@ extends:
             TeamEmail: $(TeamEmail)
             TargetBranch: $(InsertTargetBranch)
             InsertionPayloadName: $(InsertPayloadName)
-            # servicing branches until 17.12 also include Microsoft.Build.Engine and Microsoft.Build.Conversion.Core
-            ${{ if or(eq(variables['Build.SourceBranchName'], 'vs17.0'),  eq(variables['Build.SourceBranchName'], 'vs17.3'), eq(variables['Build.SourceBranchName'], 'vs17.6'),  eq(variables['Build.SourceBranchName'], 'vs17.8'), eq(variables['Build.SourceBranchName'], 'vs17.10'), eq(variables['Build.SourceBranchName'], 'vs17.11'), eq(variables['Build.SourceBranchName'], 'vs17.12')) }}: 
-              PackagePropsValues: VS.ExternalAPIs.MSBuild=$(MSBuild_ExtApisPackageVersion);Microsoft.Build=$(MicrosoftNETStringToolsPackageVersion);Microsoft.Build.Conversion.Core=$(MicrosoftNETStringToolsPackageVersion);Microsoft.Build.Engine=$(MicrosoftNETStringToolsPackageVersion);Microsoft.Build.Framework=$(MicrosoftNETStringToolsPackageVersion);Microsoft.Build.Tasks.Core=$(MicrosoftNETStringToolsPackageVersion);Microsoft.Build.Utilities.Core=$(MicrosoftNETStringToolsPackageVersion);Microsoft.NET.StringTools=$(MicrosoftNETStringToolsPackageVersion)
-            ${{ else }}:
-              PackagePropsValues: VS.ExternalAPIs.MSBuild=$(MSBuild_ExtApisPackageVersion);Microsoft.Build=$(MicrosoftNETStringToolsPackageVersion);Microsoft.Build.Framework=$(MicrosoftNETStringToolsPackageVersion);Microsoft.Build.Tasks.Core=$(MicrosoftNETStringToolsPackageVersion);Microsoft.Build.Utilities.Core=$(MicrosoftNETStringToolsPackageVersion);Microsoft.NET.StringTools=$(MicrosoftNETStringToolsPackageVersion)
+            PackagePropsValues: $(InsertPackagePropsValues)
             InsertionDescription: $(InsertDescription)
             ComponentJsonValues: $(InsertJsonValues)
             DefaultConfigValues: $(InsertConfigValues)
diff --git a/documentation/release-checklist.md b/documentation/release-checklist.md
index 911c2c59a6e..fe64e8b61c2 100644
--- a/documentation/release-checklist.md
+++ b/documentation/release-checklist.md
@@ -14,9 +14,9 @@
 ## At release time
 Before starting the process:
 - [ ] If the release is being cut more than a few days before the VS-side snap, run insertions manually OR redirect MSBuild release branch 
-  - [ ]  Disabling automated run of [MSBuild VS Insertion pipeline](https://devdiv.visualstudio.com/DevDiv/_build?definitionId=24295) (our {{NEXT_VERSION}} builds don't have a place to go in VS yet) is done by: Edit -> ... -> Triggers -> add a schedule on a dead branch (this overrides the YAML defined once-per-day schedule). Manual pipeline run: select as input resource the inserted "MSBuild" pipeline run on branch `vs{{THIS_RELEASE_VERSION}}` and VS TargetBranch `main`.
+  - [ ]  Disable scheduled run of [MSBuild VS Insertion pipeline](https://devdiv.visualstudio.com/DevDiv/_build?definitionId=24295) (our {{NEXT_VERSION}} builds don't have a place to go in VS yet) by: Edit -> ... -> Triggers -> add a schedule on a dead branch (this overrides the YAML defined once-per-day schedule for main). Manual pipeline run: select as input resource the to-be-inserted "MSBuild" pipeline run on branch `vs{{THIS_RELEASE_VERSION}}` and VS TargetBranch `main`.
 OR
-  - [ ]  If the release is being cut more than couple of weeks modify [YAML](https://github.com/dotnet/msbuild/tree/main/azure-pipelines/vs-insertion.yml) (and merge to affected MSBuild branches) of the [VS insertion pipeline](https://devdiv.visualstudio.com/DevDiv/_build?definitionId=24295) so that it flows from MSBuild `vs{{THIS_RELEASE_VERSION}}` to VS `main` [in the MSBuild VS Insertion pipeline](https://devdiv.visualstudio.com/DevDiv/_build?definitionId=24295) and keep scheduled insertions to simplify your workflow.
+  - [ ]  If the release is being cut more than couple of weeks modify [YAML](https://github.com/dotnet/msbuild/tree/main/azure-pipelines/vs-insertion.yml) (and merge to affected MSBuild branches) of the [VS insertion pipeline](https://devdiv.visualstudio.com/DevDiv/_build?definitionId=24295) so that it schedules insertions from MSBuild `vs{{THIS_RELEASE_VERSION}}` to VS `main`. Keep scheduled daily insertions to simplify your workflow and exclude `vs{{THIS_RELEASE_VERSION}}` from triggering insertion on each commit.
 
 ### Branching from main
 - [ ]  If the new version's branch was created before the Visual Studio fork: fast-forward merge the correct commit (the one that is currently inserted to VS main) to the `vs{{THIS_RELEASE_VERSION}}` branch \
@@ -28,6 +28,7 @@ _(This is for the case where we create the branch too early and want it to be ba
 `dotnet pack MSBuild.Dev.slnf /p:ApiCompatGenerateSuppressionFile=true`. 
   - [ ]  When VS main snaps to {{THIS_RELEASE_VERSION}} and updates its version to {{NEXT_VERSION}}, modify the [MSBuild VS Insertion pipeline](https://devdiv.visualstudio.com/DevDiv/_build?definitionId=24295) YAML so that it flows from MSBuild main to VS main.
     - [ ]  Update AutoTargetBranch selection in the [YAML](https://github.com/dotnet/msbuild/tree/main/azure-pipelines/vs-insertion.yml) (add to parameters and make new AutoTargetBranch rule by copying it from existing ones) of the [MSBuild VS Insertion pipeline](https://devdiv.visualstudio.com/DevDiv/_build?definitionId=24295) to insert MSBuild `vs{{THIS_RELEASE_VERSION}}` to the corresponding VS branch `rel/d{{THIS_RELEASE_VERSION}}`.
+    - [ ] Set scheduled insertion for main and remove exclusion of `vs{{THIS_RELEASE_VERSION}}` triggering on each commit if added earlier.
 - [ ]  Merge {{NEXT_VERSION}} branding PR
 
 ### Adjust DARC channels and subscriptions