diff --git a/.github/policies/labelAdded.manifestSingletonDeprecated.yml b/.github/policies/labelAdded.manifestSingletonDeprecated.yml
new file mode 100644
index 0000000000000..733e4f8a72d8f
--- /dev/null
+++ b/.github/policies/labelAdded.manifestSingletonDeprecated.yml
@@ -0,0 +1,40 @@
+id: labelAdded.manifestSingletonDeprecated
+name: GitOps.PullRequestIssueManagement
+description: Handlers when "Manifest-Singleton-Deprecated" label is added
+owner:
+resource: repository
+disabled: false
+where:
+configuration:
+  resourceManagementConfiguration:
+    eventResponderTasks:
+      - description: >-
+          When the label "Manifest-Singleton-Deprecated" is added to a pull request
+          * Add the PR specific reply notifying the issue author
+          * Assign to the Author
+          * Label with Needs-Author-Feedback
+          * Remove the Needs-Attention Label
+        if:
+          - payloadType: Pull_Request
+          - labelAdded:
+              label: Manifest-Singleton-Deprecated
+        then:
+          - addReply:
+              reply: >-
+                Hello @${issueAuthor},
+
+
+                The package manager bot determined that your submission uses a `Singleton` Manifest, which been deprecated in this repository. Please update your submission to use the newer multi-manifest format. If you built your manifest by hand, a tool like [WingetCreate](https://github.com/microsoft/winget-create) or [YamlCreate](https://github.com/microsoft/winget-pkgs/blob/master/doc/tools/YamlCreate.md) can help you build the multi-manifest.
+
+
+                Template: msftbot/validationError/manifest/singleton/deprecated
+          - assignTo:
+              author: True
+          - addLabel:
+              label: Needs-Author-Feedback
+          - removeLabel:
+              label: Needs-Attention
+        # The policy service should trigger even when the label was added by the policy service
+        triggerOnOwnActions: true
+onFailure:
+onSuccess:
diff --git a/.github/policies/labelAdded.manifestVersionDeprecated.yml b/.github/policies/labelAdded.manifestVersionDeprecated.yml
index f2a4818c1860b..2a9adb97adc78 100644
--- a/.github/policies/labelAdded.manifestVersionDeprecated.yml
+++ b/.github/policies/labelAdded.manifestVersionDeprecated.yml
@@ -9,7 +9,7 @@ configuration:
   resourceManagementConfiguration:
     eventResponderTasks:
       - description: >-
-          When the label "Manifest-Version-Error" is added to a pull request
+          When the label "Manifest-Version-Deprecated" is added to a pull request
           * Add the PR specific reply notifying the issue author
           * Assign to the Author
           * Label with Needs-Author-Feedback
diff --git a/.github/policies/labelManagement.issueOpened.yml b/.github/policies/labelManagement.issueOpened.yml
index 8afa7ee24d790..62e504d93a964 100644
--- a/.github/policies/labelManagement.issueOpened.yml
+++ b/.github/policies/labelManagement.issueOpened.yml
@@ -206,5 +206,35 @@ configuration:
         then:
           - addLabel:
               label: Author-Not-Authorized
+      - description: >-
+          When a PR is opened/updated, if
+          * The files are in /manifests
+          * The files match *.yaml
+          * The files do not match *.installer.yaml
+          * The files do no match *.locale.yaml
+          Then
+          * Add label Manifest-Singleton-Deprecated
+        if:
+          - payloadType: Pull_Request
+          - isOpen
+          - or:
+              - isAction:
+                  action: Opened
+              - isAction:
+                  action: Synchronize
+          - not:
+              filesMatchPattern: # has at least one file
+                pattern: ^$
+          - filesMatchPattern:
+                pattern: ^manifests/.*\.yaml  # matches manifests/*.yaml
+          - not:
+              filesMatchPattern:
+                pattern: ^manifests/.*\.installer\.yaml # matches manifests/*.installer.yaml
+          - not:
+              filesMatchPattern:
+                pattern: ^manifests/.*\.locale\..*\.yaml # matches manifests/*.locale.*.yaml
+        then:
+          - addLabel:
+              label: Manifest-Singleton-Deprecated
 onFailure:
 onSuccess: