diff --git a/.github/workflows/_cherry-pick.yml b/.github/workflows/_cherry-pick.yml
index f1e28051a..bed8a350b 100644
--- a/.github/workflows/_cherry-pick.yml
+++ b/.github/workflows/_cherry-pick.yml
@@ -16,11 +16,20 @@ on:
         required: false
         type: string
         default: ''
+      create_pr:
+        description: 'Create a PR to dest_branch instead of pushing directly'
+        required: false
+        type: boolean
+        default: false
       test_mode:
-        description: 'Run in test mode (skips Azure auth and GPG signing)'
+        description: 'Run in test mode (skips Azure auth and uses local token)'
         required: false
         type: boolean
         default: false
+    outputs:
+      cherry_pick_branch:
+        description: 'The cherry-pick branch created when create_pr is true, empty otherwise'
+        value: ${{ jobs.cherry-pick.outputs.cherry_pick_branch }}
     secrets:
       AZURE_SUBSCRIPTION_ID:
         required: false
@@ -34,10 +43,13 @@ permissions: {}
 jobs:
   cherry-pick:
     name: Cherry Pick Commit
+    outputs:
+      cherry_pick_branch: ${{ steps.create-cherry-pick-branch.outputs.cherry_pick_branch }}
     env:
       _SOURCE_PR: ${{ inputs.source_pr }}
       _DEST_BRANCH: ${{ inputs.dest_branch }}
       _DEST_BRANCH_ALLOWED: ${{ inputs.dest_branch_allowed }}
+      _CHERRY_PICK_BRANCH: cherry-pick/${{ inputs.source_pr }}-to-${{ inputs.dest_branch }}
     runs-on: ubuntu-24.04
     permissions:
       contents: write
@@ -48,7 +60,7 @@ jobs:
         if: inputs.dest_branch_allowed != ''
         run: |
           if ! echo "$_DEST_BRANCH" | grep -Eq "$_DEST_BRANCH_ALLOWED"; then
-            echo "ERROR: Destination branch [$_DEST_BRANCH] does not match allowed pattern [$_DEST_BRANCH_ALLOWED]"
+            echo "::error::Destination branch [$_DEST_BRANCH] does not match allowed pattern [$_DEST_BRANCH_ALLOWED]"
             exit 1
           fi
           echo "INFO: Destination branch matches allowed pattern"
@@ -94,7 +106,7 @@ jobs:
         id: validate_dest_branch
         run: |
            if ! git rev-parse --quiet --verify origin/"$_DEST_BRANCH" >/dev/null; then
-            echo "ERROR: Could not find destination branch [$_DEST_BRANCH]. Please confirm the branch exists and the name is correct."
+            echo "::error::Could not find destination branch [$_DEST_BRANCH]. Please confirm the branch exists and the name is correct."
             exit 1
            fi
 
@@ -105,45 +117,48 @@ jobs:
           WORKFLOW_REF: ${{ github.workflow_ref }}
         run: |
           # get PR info
-          if ! pr_info=$(gh pr view "$_SOURCE_PR" --json state,baseRefName,mergeCommit); then
-            echo "ERROR: Could not gather data for PR [#$_SOURCE_PR]. Please verify the number."
+          if ! pr_info=$(gh pr view "$_SOURCE_PR" --json state,baseRefName,mergeCommit,title); then
+            echo "::error::Could not gather data for PR [#$_SOURCE_PR]. Please verify the number."
             exit 1
           fi
 
           pr_state=$(echo "$pr_info" | jq -r .state)
           pr_base_ref=$(echo "$pr_info" | jq -r .baseRefName)
           pr_commit=$(echo "$pr_info" | jq -r .mergeCommit.oid)
+          pr_title=$(echo "$pr_info" | jq -r .title)
 
           echo "INFO: PR state: [$pr_state]"
           echo "INFO: PR base ref: [$pr_base_ref]"
           echo "INFO: PR commit: [$pr_commit]"
+          echo "INFO: PR title: [$pr_title]"
           echo "INFO: Calling workflow: [$WORKFLOW_REF]"
 
           # if this is being run by the test-cherry-pick workflow, allow picking from the simulated main branch
           if [[ $WORKFLOW_REF == bitwarden/gh-actions/.github/workflows/test-cherry-pick.yml@* ]]; then
               echo "INFO: This workflow is being run by the [test-cherry-pick.yml] workflow."
               if [[ ${pr_base_ref:0:21} != "cherry-pick-sim-main-" ]]; then
-                echo "ERROR: Invalid test base ref: [$pr_base_ref]. Test ref/branch must match [cherry-pick-sim-main-*]"
+                echo "::error::Invalid test base ref: [$pr_base_ref]. Test ref/branch must match [cherry-pick-sim-main-*]"
                 exit 1
               fi
           else
             if [[ $pr_base_ref != 'main' ]]; then      
-              echo "ERROR: Invalid PR base ref: [$pr_base_ref]. Base ref/branch must be [main]."
+              echo "::error::Invalid PR base ref: [$pr_base_ref]. Base ref/branch must be [main]."
               exit 1
             fi
           fi
 
           if [[ $pr_state != 'MERGED' ]]; then
-            echo "ERROR: Invalid PR state: [$pr_state]. State must be [MERGED]."
+            echo "::error::Invalid PR state: [$pr_state]. State must be [MERGED]."
             exit 1
           fi
 
           if [[ -z $pr_commit ]]; then
-            echo "ERROR: GitHub API returned empty commit for PR. Cannot continue."
+            echo "::error::GitHub API returned empty commit for PR. Cannot continue."
             exit 1
           fi
 
           echo "pr_commit=$pr_commit" >> $GITHUB_OUTPUT
+          echo "pr_title=$pr_title" >> $GITHUB_OUTPUT
 
       - name: Checkout dest branch
         uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
@@ -153,6 +168,14 @@ jobs:
           persist-credentials: true
           fetch-depth: 0
 
+      - name: Create cherry-pick branch
+        if: inputs.create_pr
+        id: create-cherry-pick-branch
+        run: |
+          git checkout -b "$_CHERRY_PICK_BRANCH"
+          echo "INFO: Created branch [$_CHERRY_PICK_BRANCH] from [$_DEST_BRANCH]"
+          echo "cherry_pick_branch=$_CHERRY_PICK_BRANCH" >> $GITHUB_OUTPUT
+
       - name: Configure git
         run: |
           git config --local user.name "bitwarden-devops-bot"
@@ -161,31 +184,66 @@ jobs:
       - name: Cherry pick
         env:
           PR_COMMIT: ${{ steps.validate-pr.outputs.pr_commit }}
-          GH_TOKEN: ${{ inputs.test_mode && github.token || steps.app-token.outputs.token }}
         run: |
-          echo "INFO: Cherry-picking commit [$PR_COMMIT] from PR [#$_SOURCE_PR] to branch [$_DEST_BRANCH]"
+          echo "INFO: Cherry-picking commit [$PR_COMMIT] from PR [#$_SOURCE_PR]"
           if ! git cherry-pick -x "$PR_COMMIT"; then
-            echo "ERROR: Cherry-pick failed for commit [$PR_COMMIT]"
+            echo "::error::Cherry-pick failed for commit [$PR_COMMIT]"
             git cherry-pick --abort
             exit 1
           fi
           echo 'INFO: Cherry pick successful!'
 
+      - name: Push to destination branch
+        if: ${{ !inputs.create_pr }}
+        env:
+          GH_TOKEN: ${{ inputs.test_mode && github.token || steps.app-token.outputs.token }}
+        run: |
           echo "INFO: Pushing local [$_DEST_BRANCH] branch to origin"
           if ! git push origin "$_DEST_BRANCH"; then
-            echo "ERROR: Failed to push to origin."
+            echo "::error::Failed to push to origin."
             exit 1
           fi
 
           echo "INFO: Adding 'cherry-picked' label to PR [#$_SOURCE_PR]"
           if ! gh pr edit "$_SOURCE_PR" --add-label "cherry-picked"; then
-            echo "WARN: Failed to add label to PR [#$_SOURCE_PR]"
+            echo "::warning::Failed to add label to PR [#$_SOURCE_PR]"
           fi
 
           run_url="https://github.com/${GITHUB_REPOSITORY}/actions/runs/${GITHUB_RUN_ID}"
           echo "INFO: Adding comment to PR [#$_SOURCE_PR]"
-          if ! gh pr comment "$_SOURCE_PR" --body "✅ Successfully cherry-picked to \`$_DEST_BRANCH\`. [View run]($run_url)"; then
-            echo "WARN: Failed to add comment to PR [#$_SOURCE_PR]"
+          if ! gh pr comment "$_SOURCE_PR" --body "✅ Successfully cherry-picked to [$_DEST_BRANCH]. [View run]($run_url)"; then
+            echo "::warning::Failed to add comment to PR [#$_SOURCE_PR]"
           fi
 
+      - name: Push branch and open PR
+        if: inputs.create_pr
+        env:
+          GH_TOKEN: ${{ inputs.test_mode && github.token || steps.app-token.outputs.token }}
+          PR_TITLE: ${{ steps.validate-pr.outputs.pr_title }}
+        run: |
+          echo "INFO: Pushing branch [$_CHERRY_PICK_BRANCH] to origin"
+          if ! git push origin "$_CHERRY_PICK_BRANCH"; then
+            echo "::error::Failed to push branch [$_CHERRY_PICK_BRANCH]."
+            exit 1
+          fi
+
+          run_url="https://github.com/${GITHUB_REPOSITORY}/actions/runs/${GITHUB_RUN_ID}"
+
+          PR_BODY="🍒 Automated cherry-pick of PR [#$_SOURCE_PR] to [$_DEST_BRANCH]. [View run]($run_url)"
+
+          if ! new_pr_url=$(gh pr create \
+            --base "$_DEST_BRANCH" \
+            --head "$_CHERRY_PICK_BRANCH" \
+            --title "Cherry pick: $PR_TITLE" \
+            --body "$PR_BODY"); then
+            echo "::error::Failed to create PR."
+            exit 1
+          fi
+
+          echo "INFO: Cherry-pick PR created: [$new_pr_url]"
+
+          if ! gh pr comment "$_SOURCE_PR" --body "🍒 Cherry-pick PR created targeting [$_DEST_BRANCH]: $new_pr_url. [View run]($run_url)"; then
+            echo "::warning::Failed to add comment to PR [#$_SOURCE_PR]"
+          fi
 
+          echo "🍒 Cherry-pick PR created: [Here]($new_pr_url)." >> $GITHUB_STEP_SUMMARY
diff --git a/.github/workflows/test-cherry-pick.yml b/.github/workflows/test-cherry-pick.yml
index f91b030df..64a6c99fd 100644
--- a/.github/workflows/test-cherry-pick.yml
+++ b/.github/workflows/test-cherry-pick.yml
@@ -56,7 +56,7 @@ jobs:
             git add "$sim_branch.txt"
             git commit -m 'created test file'
             if ! git push origin "$sim_branch"; then
-              echo "ERROR: Failed to push [$sim_branch] branch to origin. Exiting."
+              echo "::error::Failed to push [$sim_branch] branch to origin. Exiting."
               exit 1
             fi
             git switch main
@@ -71,12 +71,12 @@ jobs:
             --body "Automated test PR for cherry-pick workflow testing. This should be cleaned up automatically and can safely be deleted if cleanup has failed."
 
           if [[ $? -ne 0 ]]; then
-            echo "ERROR: Failed to create PR from [$simulated_feature_branch] branch to [$simulated_main_branch]. Exiting"
+            echo "::error::Failed to create PR from [$simulated_feature_branch] branch to [$simulated_main_branch]. Exiting"
             exit 1
           fi
 
           if ! simulated_pr_number=$(gh pr view "$simulated_feature_branch" --json number --jq '.number'); then
-            echo "ERROR: Failed to retrieve simulated PR number from [$simulated_feature_branch]. Exiting."
+            echo "::error::Failed to retrieve simulated PR number from [$simulated_feature_branch]. Exiting."
             exit 1
           fi
           echo "simulated_pr_number=$simulated_pr_number" >> $GITHUB_OUTPUT
@@ -84,15 +84,31 @@ jobs:
           
           echo "INFO: Merging PR [#$simulated_pr_number] into branch [$simulated_main_branch]"
           if ! gh pr merge "$simulated_pr_number" --squash; then
-            echo "ERROR: Failed to merge PR [#$simulated_pr_number]. Exiting."
+            echo "::error::Failed to merge PR [#$simulated_pr_number]. Exiting."
             exit 1
           fi
 
 
+  cherry-pick-pr:
+    # Call the cherry-pick.yml workflow in PR mode and pass in the simulated branches and PR.
+    name: Cherry-pick-pr
+    needs: setup
+    uses: ./.github/workflows/_cherry-pick.yml
+    with:
+      source_pr: ${{ needs.setup.outputs.simulated_pr_number }}
+      dest_branch: ${{ needs.setup.outputs.simulated_dest_branch }}
+      dest_branch_allowed: '^cherry-pick-sim-dest-[0-9]{10}$'
+      test_mode: true
+      create_pr: true
+    permissions:
+      contents: write
+      pull-requests: write
+      id-token: write
+
   cherry-pick:
     # Call the cherry-pick.yml workflow and pass in the simulated branches and PR.
     name: Cherry-pick
-    needs: setup
+    needs: [setup, cherry-pick-pr]
     uses: ./.github/workflows/_cherry-pick.yml
     with:
       source_pr: ${{ needs.setup.outputs.simulated_pr_number }}
@@ -108,13 +124,14 @@ jobs:
     # Cleanup all the simulated resources
     name: Cleanup Simulated Resources
     runs-on: ubuntu-24.04
-    needs: [setup, cherry-pick]
+    needs: [setup, cherry-pick-pr, cherry-pick]
     if: always()
     env:
       _SIMULATED_MAIN_BRANCH: ${{ needs.setup.outputs.simulated_main_branch }}
       _SIMULATED_FEATURE_BRANCH: ${{ needs.setup.outputs.simulated_feature_branch }}
       _SIMULATED_DEST_BRANCH: ${{ needs.setup.outputs.simulated_dest_branch }}
       _SIMULATED_PR_NUMBER: ${{ needs.setup.outputs.simulated_pr_number }}
+      _CHERRY_PICK_BRANCH: ${{ needs.cherry-pick-pr.outputs.cherry_pick_branch }}
     permissions:
       contents: write
       pull-requests: write
@@ -128,12 +145,13 @@ jobs:
         env:
           GH_TOKEN: ${{ github.token }}
         run: |
+          sleep 120
           if [[ -n $_SIMULATED_PR_NUMBER ]]; then
             pr_state=$(gh pr view "$_SIMULATED_PR_NUMBER" --json state --jq '.state')
             if [[ $pr_state == 'OPEN' ]]; then
               echo "INFO: Closing simulated PR [#$_SIMULATED_PR_NUMBER]"
               if ! gh pr close "$_SIMULATED_PR_NUMBER"; then
-                echo "WARN: Failed to close PR [#$_SIMULATED_PR_NUMBER]. Please manually delete these."
+                echo "::warning::Failed to close PR [#$_SIMULATED_PR_NUMBER]. Please manually delete these."
               fi
             fi
           fi
@@ -142,7 +160,7 @@ jobs:
             if git ls-remote --exit-code --heads origin "$_SIMULATED_FEATURE_BRANCH" >/dev/null 2>&1; then
               echo "INFO: Deleting simulated feature branch [$_SIMULATED_FEATURE_BRANCH]"
               if ! git push origin --delete "$_SIMULATED_FEATURE_BRANCH"; then
-                echo "WARN: Failed to delete [$_SIMULATED_FEATURE_BRANCH] branch. Please manually delete this."
+                echo "::warning::Failed to delete [$_SIMULATED_FEATURE_BRANCH] branch. Please manually delete this."
               fi
             else
               echo "INFO: Branch [$_SIMULATED_FEATURE_BRANCH] does not exist or was already deleted."
@@ -153,18 +171,29 @@ jobs:
             if git ls-remote --exit-code --heads origin "$_SIMULATED_MAIN_BRANCH" >/dev/null 2>&1; then
               echo "INFO: Deleting simulated main branch [$_SIMULATED_MAIN_BRANCH]"
               if ! git push origin --delete "$_SIMULATED_MAIN_BRANCH"; then
-                echo "WARN: Failed to delete [$_SIMULATED_MAIN_BRANCH] branch. Please manually delete this."
+                echo "::warning::Failed to delete [$_SIMULATED_MAIN_BRANCH] branch. Please manually delete this."
               fi
             else
               echo "INFO: Branch [$_SIMULATED_MAIN_BRANCH] does not exist or was already deleted."
             fi
           fi
 
+          if [[ -n $_CHERRY_PICK_BRANCH ]]; then
+            if git ls-remote --exit-code --heads origin "$_CHERRY_PICK_BRANCH" >/dev/null 2>&1; then
+              echo "INFO: Deleting cherry-pick branch [$_CHERRY_PICK_BRANCH]"
+              if ! git push origin --delete "$_CHERRY_PICK_BRANCH"; then
+                echo "::warning::Failed to delete [$_CHERRY_PICK_BRANCH] branch. Please manually delete this."
+              fi
+            else
+              echo "INFO: Branch [$_CHERRY_PICK_BRANCH] does not exist or was already deleted."
+            fi
+          fi
+
           if [[ -n $_SIMULATED_DEST_BRANCH ]]; then
             if git ls-remote --exit-code --heads origin "$_SIMULATED_DEST_BRANCH" >/dev/null 2>&1; then
               echo "INFO: Deleting simulated destination branch [$_SIMULATED_DEST_BRANCH]"
               if ! git push origin --delete "$_SIMULATED_DEST_BRANCH"; then
-                echo "WARN: Failed to delete [$_SIMULATED_DEST_BRANCH] branch. Please manually delete this."
+                echo "::warning::Failed to delete [$_SIMULATED_DEST_BRANCH] branch. Please manually delete this."
               fi
             else
               echo "INFO: Branch [$_SIMULATED_DEST_BRANCH] does not exist or was already deleted."
diff --git a/cherry-pick/cherry-pick.yml b/cherry-pick/cherry-pick.yml
index 6d705081d..be07ba030 100644
--- a/cherry-pick/cherry-pick.yml
+++ b/cherry-pick/cherry-pick.yml
@@ -16,6 +16,11 @@ on:
           - rc
           - hotfix-rc
           - rc-2024-02
+      create_pr:
+        description: 'Create a PR to dest_branch instead of pushing directly'
+        required: false
+        type: boolean
+        default: false
 
 # It's also possible to provide `dest_branch` as a free-form string input
 #      dest_branch:
@@ -35,6 +40,7 @@ jobs:
       # Optionally validate `dest_branch` by providing an extended regex expression (ERE) pattern that `dest_branch` must match. Leave empty ('') to disable.
       # dest_branch_allowed: '^20[2-9][0-9]\.[0-9][0-9]\-rc[0-9]$' # matches format `2025.01-rc2`
       dest_branch_allowed: ''
+      create_pr: ${{ inputs.create_pr }}
     permissions:
       contents: read
       id-token: write