diff --git a/.github/workflows/run-since-updater.yml b/.github/workflows/run-since-updater.yml
new file mode 100644
index 000000000000..03bcfe5b7c9d
--- /dev/null
+++ b/.github/workflows/run-since-updater.yml
@@ -0,0 +1,41 @@
+name: Run update-since-todo.py
+
+on:
+  schedule:
+    - cron: "0 16 * * THU"
+  workflow_dispatch:
+
+permissions:
+  contents: write
+  pull-requests: write
+
+jobs:
+  since_updater:
+    runs-on: ubuntu-latest
+    if: ${{ github.repository_owner == 'jenkinsci' }}
+    steps:
+      - uses: actions/checkout@v4
+        with:
+          fetch-depth: 0
+      - name: Run update-since-todo.py
+        run: |
+          body=$(./update-since-todo.py)
+
+          {
+            echo 'PROGRESS<<EOF'
+            echo "${body}"
+            echo 'EOF'
+          } >> $GITHUB_OUTPUT
+        id: run_script
+        shell: bash
+      - name: Create Pull Request
+        uses: peter-evans/create-pull-request@8867c4aba1b742c39f8d0ba35429c2dfa4b6cb20 # v7
+        with:
+          token: ${{ secrets.GITHUB_TOKEN }}
+          commit-message: Fill in since annotations
+          title: Fill in since annotations
+          body: ${{ steps.run_script.outputs.PROGRESS }}
+          base: master
+          labels: skip-changelog
+          branch: actions/update-since-todo
+          delete-branch: true
diff --git a/update-since-todo.py b/update-since-todo.py
index 044d441a935e..3b0241a9928f 100755
--- a/update-since-todo.py
+++ b/update-since-todo.py
@@ -3,6 +3,7 @@
 import argparse
 import fileinput
 import io
+import os
 import shutil
 import subprocess
 
@@ -18,7 +19,7 @@ def update_file(file, lineno, old, new):
     :param old: The old substring.
     :param new: The new substring.
     """
-    print("\tUpdating file in place")
+    print("* Updating file in place")
     with fileinput.FileInput(file, inplace=True) as f:
         for line in f:
             if f.lineno() == lineno and old in line:
@@ -44,13 +45,13 @@ def analyze_file(file, lineno, commits_and_tags, dry_run=False):
         .split("\n", 1)[0]
         .split(" ", 1)[0]
     )
-    print(f"\tfirst sha: {line_sha}")
+    print(f"* first sha: {line_sha}")
     first_tag = subprocess.check_output(
         [GIT, "tag", "--sort=creatordate", "--contains", line_sha, "jenkins-*"],
         text=True,
     ).split("\n", 1)[0]
     if first_tag:
-        print(f"\tfirst tag was {first_tag}")
+        print(f"* first tag was {first_tag}")
         commits_and_tags[line_sha] = first_tag
         if not dry_run:
             since_version = first_tag.replace("jenkins-", "")
@@ -75,10 +76,11 @@ def analyze_file(file, lineno, commits_and_tags, dry_run=False):
 
     else:
         print(
-            "\tNot updating file, no tag found. "
+            "* Not updating file, no tag found. "
             "Normal if the associated PR/commit is not merged and released yet; "
             "otherwise make sure to fetch tags from jenkinsci/jenkins"
         )
+    print() # Add a newline for markdown rendering
 
 
 def analyze_files(commits_and_tags, dry_run=False):
@@ -99,6 +101,10 @@ def analyze_files(commits_and_tags, dry_run=False):
         "*.jelly",
         "*.js",
     ]
+
+    runningInCI = os.environ.get("CI", "false") == "true"
+    if runningInCI:
+        print("<details><summary>Detailed output</summary>\n\n")
     with subprocess.Popen(cmd, stdout=subprocess.PIPE) as proc:
         for line in io.TextIOWrapper(proc.stdout):
             parts = line.rstrip().split(":", 2)
@@ -107,6 +113,8 @@ def analyze_files(commits_and_tags, dry_run=False):
         if retcode:
             raise subprocess.CalledProcessError(retcode, cmd)
     print()
+    if runningInCI:
+        print("</details>\n")
 
 
 def display_results(commits_and_tags):