diff --git a/.github/workflows/maintenance.yml b/.github/workflows/maintenance.yml
new file mode 100644
index 000000000000..7c7601dd18fe
--- /dev/null
+++ b/.github/workflows/maintenance.yml
@@ -0,0 +1,46 @@
+name: Winbindex maintenance
+
+on:
+  workflow_dispatch:
+  schedule:
+    - cron: '0 1 1 * *'
+
+concurrency: winbindex-maintenance
+
+jobs:
+  run:
+    runs-on: ubuntu-latest
+    steps:
+      - name: Checkout main
+        uses: actions/checkout@v4
+        with:
+          ref: main
+      - name: Checkout gh-pages
+        uses: actions/checkout@v4
+        with:
+          ref: gh-pages
+          path: gh-pages
+          fetch-depth: 0
+          filter: 'blob:none'
+      - name: Override out_path
+        run: |
+          echo ./gh-pages/data > data/.out_path_override
+      - name: Squash old commits
+        run: ./data/maintenance_squash_old_commits.sh gh-pages "30 days ago"
+      - name: Push squashed repo gradually with temporary sliding tags
+        run: |
+          cd gh-pages
+          for i in $(git rev-list --reverse HEAD); do
+            echo "Pushing $i"
+            git tag "_temp_tag_for_squash_$i" "$i"
+            git push origin tag "_temp_tag_for_squash_$i"
+          done
+      - name: Push squashed repo
+        run: git -C gh-pages push --force-with-lease
+      - name: Remove temporary sliding tags
+        run: |
+          cd gh-pages
+          for i in $(git rev-list --reverse HEAD); do
+            git tag -d "_temp_tag_for_squash_$i"
+            git push origin -d "_temp_tag_for_squash_$i"
+          done
diff --git a/data/maintenance_squash_old_commits.sh b/data/maintenance_squash_old_commits.sh
new file mode 100644
index 000000000000..01318742014c
--- /dev/null
+++ b/data/maintenance_squash_old_commits.sh
@@ -0,0 +1,41 @@
+#!/bin/bash
+
+# Check if the repository path is provided
+if [ -z "$1" ] || [ -z "$2" ]; then
+  echo "Usage: $0 /path/to/repository keep_since_time"
+  exit 1
+fi
+
+REPO_PATH=$1
+KEEP_SINCE=$2  # e.g. "7 days ago"
+
+# Change to the target repository
+cd "$REPO_PATH" || { echo "Repository not found at $REPO_PATH"; exit 1; }
+
+# Ensure the working directory is clean
+if ! git diff-index --quiet HEAD --; then
+  echo "Your working directory is not clean. Commit or stash your changes first."
+  exit 1
+fi
+
+# Squash old commits
+for i in $(git log --since="$KEEP_SINCE" --format=%H --reverse); do
+  if [ -z "$new_commit" ]; then
+    if [ "$(git rev-list "$i" --children)" == "$i" ]; then
+        echo No commits to squash
+        exit
+    fi
+
+    # How to remove only the first occurrence of a line in a file using sed: https://stackoverflow.com/q/23696871
+    msg=$(git cat-file commit "$i" | sed "0,/^parent /{//d}")
+    msg+=$'\n\n========================================\nSquashed history:\n\n'
+    msg+=$(git log --first-parent "$i~" | sed -r 's/^[[:blank:]]+//')
+  else
+    msg=$(git cat-file commit "$i" | sed "s/$i_prev/$new_commit/")
+  fi
+  new_commit=$(echo "$msg" | git hash-object -t commit -w --stdin)
+  echo "$i -> $new_commit"
+  i_prev=$i
+done
+
+git reset $new_commit