diff --git a/.github/workflows/updatecli.yaml b/.github/workflows/updatecli.yaml
new file mode 100644
index 00000000..3ba9201d
--- /dev/null
+++ b/.github/workflows/updatecli.yaml
@@ -0,0 +1,29 @@
+name: updatecli
+on:
+  # Allow to be run manually
+  workflow_dispatch:
+  schedule:
+    # Run once per week (to avoid alert fatigue)
+    - cron: '0 2 * * 1' # Every Monday at 2am UTC
+  push:
+  pull_request:
+jobs:
+  updatecli:
+    runs-on: ubuntu-latest
+    steps:
+      - name: Checkout
+        uses: actions/checkout@v3
+
+      - name: Install Updatecli in the runner
+        uses: updatecli/updatecli-action@v2.21.0
+
+      - name: Run Updatecli in Dry Run mode
+        run: updatecli diff --config ./updatecli/updatecli.d --values ./updatecli/values.github-action.yaml
+        env:
+          UPDATECLI_GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+
+      - name: Run Updatecli in Apply mode
+        if: github.ref == 'refs/heads/master'
+        run: updatecli apply --config ./updatecli/updatecli.d --values ./updatecli/values.github-action.yaml
+        env:
+          UPDATECLI_GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
diff --git a/updatecli/updatecli.d/git-windows.yml b/updatecli/updatecli.d/git-windows.yml
new file mode 100644
index 00000000..88c99e44
--- /dev/null
+++ b/updatecli/updatecli.d/git-windows.yml
@@ -0,0 +1,151 @@
+---
+name: Bump Git version on Windows
+
+scms:
+  default:
+    kind: github
+    spec:
+      user: "{{ .github.user }}"
+      email: "{{ .github.email }}"
+      owner: "{{ .github.owner }}"
+      repository: "{{ .github.repository }}"
+      token: "{{ requiredEnv .github.token }}"
+      username: "{{ .github.username }}"
+      branch: "{{ .github.branch }}"
+
+sources:
+  lastVersion:
+    kind: githubrelease
+    name: Get the latest Git version
+    spec:
+      owner: "git-for-windows"
+      repository: "git"
+      token: "{{ requiredEnv .github.token }}"
+      username: "{{ .github.username }}"
+      versionfilter:
+        kind: regex
+        ## Latest stable v{x.y.z}.windows.<patch>
+        pattern: 'v(\d*)\.(\d*)\.(\d*)\.windows\.(\d*)$'
+    transformers:
+      - trimprefix: "v"
+
+targets:
+  ############# JDK11 Nanoserver 18.09
+  setGitVersionJDK11WindowsNanoserver1809:
+    name: Update the Git Windows version for JDK11 Windows Nanoserver 1809
+    transformers:
+      - findsubmatch:
+          pattern: '(.*).windows\.(\d*)$'
+          captureindex: 1
+    kind: dockerfile
+    spec:
+      file: 11/windows/nanoserver-ltsc2019/Dockerfile
+      instruction:
+        keyword: ARG
+        matcher: GIT_VERSION
+    scmid: default
+  setGitPackagePatchJDK11WindowsNanoserver1809:
+    name: Update the Git Package Windows patch for JDK11 Windows Nanoserver 1809
+    transformers:
+      - findsubmatch:
+          pattern: '(.*).windows\.(\d*)$'
+          captureindex: 2
+    kind: dockerfile
+    spec:
+      file: 11/windows/nanoserver-ltsc2019/Dockerfile
+      instruction:
+        keyword: ARG
+        matcher: GIT_PATCH_VERSION
+    scmid: default
+  ############# JDK11 Windows Server Core LTSC2019
+  setGitVersionJDK11WindowsServer2019:
+    name: Update the Git Windows version for JDK11 Windows Server Core LTSC2019
+    transformers:
+      - findsubmatch:
+          pattern: '(.*).windows\.(\d*)$'
+          captureindex: 1
+    kind: dockerfile
+    spec:
+      file: 11/windows/windowsservercore-ltsc2019/Dockerfile
+      instruction:
+        keyword: ARG
+        matcher: GIT_VERSION
+    scmid: default
+  setGitPackagePatchJDK11WindowsServer2019:
+    name: Update the Git Package Windows patch for Windows Server Core LTSC2019
+    transformers:
+      - findsubmatch:
+          pattern: '(.*).windows\.(\d*)$'
+          captureindex: 2
+    kind: dockerfile
+    spec:
+      file: 11/windows/windowsservercore-ltsc2019/Dockerfile
+      instruction:
+        keyword: ARG
+        matcher: GIT_PATCH_VERSION
+    scmid: default
+  ############# JDK8 Nanoserver 18.09
+  setGitVersionJDK8WindowsNanoserver1809:
+    name: Update the Git Windows version for JDK8 Windows Nanoserver 1809
+    transformers:
+      - findsubmatch:
+          pattern: '(.*).windows\.(\d*)$'
+          captureindex: 1
+    kind: dockerfile
+    spec:
+      file: 8/windows/nanoserver-ltsc2019/Dockerfile
+      instruction:
+        keyword: ARG
+        matcher: GIT_VERSION
+    scmid: default
+  setGitPackagePatchJDK8WindowsNanoserver1809:
+    name: Update the Git Package Windows patch for JDK8 Windows Nanoserver 1809
+    transformers:
+      - findsubmatch:
+          pattern: '(.*).windows\.(\d*)$'
+          captureindex: 2
+    kind: dockerfile
+    spec:
+      file: 8/windows/nanoserver-ltsc2019/Dockerfile
+      instruction:
+        keyword: ARG
+        matcher: GIT_PATCH_VERSION
+    scmid: default
+  ############# JDK8 Windows Server Core LTSC2019
+  setGitVersionJDK8WindowsServer2019:
+    name: Update the Git Windows version for JDK8 Windows Server Core LTSC2019
+    transformers:
+      - findsubmatch:
+          pattern: '(.*).windows\.(\d*)$'
+          captureindex: 1
+    kind: dockerfile
+    spec:
+      file: 8/windows/windowsservercore-ltsc2019/Dockerfile
+      instruction:
+        keyword: ARG
+        matcher: GIT_VERSION
+    scmid: default
+  setGitPackagePatchJDK8WindowsServer2019:
+    name: Update the Git Package Windows patch for JDK8 Windows Server Core LTSC2019
+    transformers:
+      - findsubmatch:
+          pattern: '(.*).windows\.(\d*)$'
+          captureindex: 2
+    kind: dockerfile
+    spec:
+      file: 8/windows/windowsservercore-ltsc2019/Dockerfile
+      instruction:
+        keyword: ARG
+        matcher: GIT_PATCH_VERSION
+    scmid: default
+
+actions:
+  default:
+    kind: github/pullrequest
+    title: Bump Git version on Windows to {{ source "lastVersion" }}
+    scmid: default
+    spec:
+      labels:
+        - enhancement
+        - git
+        - windows
diff --git a/updatecli/values.github-action.yaml b/updatecli/values.github-action.yaml
new file mode 100644
index 00000000..6d94bf03
--- /dev/null
+++ b/updatecli/values.github-action.yaml
@@ -0,0 +1,8 @@
+github:
+  user: "GitHub Actions"
+  email: "41898282+github-actions[bot]@users.noreply.github.com"
+  username: "github-actions"
+  token: "UPDATECLI_GITHUB_TOKEN"
+  branch: "master"
+  owner: "jenkinsci"
+  repository: "docker-ssh-agent"