diff --git a/.github/workflows/post-release.yml b/.github/workflows/post-release.yml
index 31bb7dc23c5..c9454db35ef 100644
--- a/.github/workflows/post-release.yml
+++ b/.github/workflows/post-release.yml
@@ -10,52 +10,112 @@ env:
     GIT_AUTHOR_EMAIL: 'no-reply@woocommerce.com'
 
 jobs:
-  update-changelog-in-trunk:
-    name: Update changelog in trunk
+  changelog-version-update:
+    name: Update changelog and version
     runs-on: ubuntu-20.04
     steps:
       - uses: actions/checkout@v3
-      - name: Get tag name
-        id: tag
-        uses: actions/github-script@v6
-        with:
-          script: |
-            const tag = ${{ toJSON( github.event.release.tag_name ) }}
-
-            console.log( `::set-output name=tag::release/${ tag.substring( 0, 3 ) }` )
 
       - name: Git fetch trunk branch
         run: git fetch origin trunk
 
-      - name: Copy changelog.txt to vm root
-        run: cp changelog.txt ../../changelog.txt
+      - name: Copy readme.txt to vm root
+        run: cp ./plugins/woocommerce/readme.txt ../../readme.txt
 
       - name: Switch to trunk branch
         run: git checkout trunk
-      
-      - name: Create a new branch based on trunk
-        run: git checkout -b update/changelog-from-release-${{ github.event.release.tag_name }}
 
-      - name: Copy saved changelog.txt to monorepo
-        run: cp ../../changelog.txt ./changelog.txt
+      - name: Create a new branch based on trunk
+        run: git checkout -b prep/post-release-tasks-${{ github.event.release.tag_name }}
+
+      - name: Check if we need to continue processing
+        uses: actions/github-script@v6
+        id: check
+        with:
+          script: |
+            const fs = require( 'node:fs' );
+            const version = ${{ toJSON( github.event.release.tag_name ) }}
+
+            fs.readFile( './plugins/woocommerce/readme.txt', 'utf-8', function( err, data ) {
+              if ( err ) {
+                console.error( err );
+              }
+
+              const regex = /Stable\stag:\s(\d+\.\d+\.\d+)/;
+
+              const stableVersion = data.match( regex )[1];
+
+              // If the release version is less than stable version we can bail.
+              if ( version.localeCompare( stableVersion, undefined, { numeric: true, sensitivity: 'base' } ) == -1 ) {
+                console.log( 'Release version is less than stable version. No automated action taken. A manual process is required.' );
+                console.log( `::set-output name=continue::false` )
+                return;
+              } else {
+                console.log( `::set-output name=continue::true` )
+              }
+            } )
+
+      - name: Update changelog.txt entries
+        uses: actions/github-script@v6
+        id: update-entries
+        if: steps.check.outputs.continue == 'true'
+        with:
+          script: |
+            const fs = require( 'node:fs' );
+            const version = ${{ toJSON( github.event.release.tag_name ) }}
+
+            // Read the saved readme.txt file from earlier.
+            fs.readFile( '../../readme.txt', 'utf-8', function( err, readme ) {
+              if ( err ) {
+                console.log( `::set-output name=continue::false` )
+                console.error( err );
+              }
+
+              const regex = /(== Changelog ==[\s\S]+)\s{2}\[See changelog for all versions\]\(https:\/\/raw\.githubusercontent\.com\/woocommerce\/woocommerce\/trunk\/changelog\.txt\)\./;
+
+              const entries = readme.match( regex )[1];
+
+              fs.readFile( './changelog.txt', 'utf-8', function( err, changelog ) {
+                if ( err ) {
+                  console.log( `::set-output name=continue::false` )
+                  console.error( err );
+                }
+
+                const regex = /== Changelog ==/;
+
+                const updatedChangelog = changelog.replace( regex, entries );
+
+                fs.writeFile( './changelog.txt', updatedChangelog, err => {
+                  if ( err ) {
+                    console.log( `::set-output name=continue::false` )
+                    console.error( 'Unable to update changelog entries in changelog.txt' );
+                  }
+
+                  console.log( `::set-output name=continue::true` )
+                } )
+              } )
+            } )
 
       - name: Commit changes
-        run: git commit -am "Update changelog.txt from release ${{ github.event.release.tag_name }}"
+        if: steps.update-entries.outputs.continue == 'true'
+        run: git commit -am "Prep trunk post release ${{ github.event.release.tag_name }}"
 
       - name: Push branch up
-        run: git push origin update/changelog-from-release-${{ github.event.release.tag_name }}
+        if: steps.update-entries.outputs.continue == 'true'
+        run: git push origin prep/post-release-tasks-${{ github.event.release.tag_name }}
 
       - name: Create the PR
+        if: steps.update-entries.outputs.continue == 'true'
         uses: actions/github-script@v6
         with:
           script: |
-            const body = "This PR updates the changelog.txt based on the latest release: ${{ github.event.release.tag_name }}"
+            const body = "This PR updates the changelog.txt entries based on the latest release: ${{ github.event.release.tag_name }}"
 
             const pr = await github.rest.pulls.create({
               owner: context.repo.owner,
               repo: context.repo.repo,
               title: "Update changelog.txt from release ${{ github.event.release.tag_name }}",
-              head: "update/changelog-from-release-${{ github.event.release.tag_name }}",
+              head: "prep/post-release-tasks-${{ github.event.release.tag_name }}",
               base: "trunk",
               body: body
             })