Every time a service gets added to the Caddyfile, we want it in the bookmarks bar without manual work. The Caddyfile is the source of truth — if it’s routed through Caddy, it should be a bookmark.

The script reads /Users/bee/tmp-immich-stack/caddy-ct103-Caddyfile, extracts every @matcher host ... entry, and rebuilds a flat alphabetical list inside a folder named edmd.me Services in Brave’s bookmarks bar.

Item	Value
Script	/Users/bee/tmp-immich-stack/sync-bookmarks.py
Reads	/Users/bee/tmp-immich-stack/caddy-ct103-Caddyfile
Writes	~/Library/Application Support/BraveSoftware/Brave-Browser/Default/Bookmarks
Backup	Same dir, .bak.YYYYMMDD-HHMMSS files
Folder name	edmd.me Services
Structure	Flat alphabetical list (aliases included as separate entries)

The script quits Brave before editing (Brave overwrites the file in memory), makes a timestamped backup, removes any existing folder with that name, rebuilds it, and relaunches Brave.

To keep bookmarks auto-updated without manual runs, add to crontab -e:

0 */6 * * * /usr/bin/python3 /Users/bee/tmp-immich-stack/sync-bookmarks.py --no-restart >> ~/Library/Logs/sync-bookmarks.log 2>&1

That runs every 6 hours. The --no-restart flag means Brave isn’t interrupted — the bookmarks file is edited in place and Brave picks up the changes on its next read (typically the next launch, or within a minute for the current session).

1. Add the @matcher host newservice.edmd.me + handle @matcher block to /Users/bee/tmp-immich-stack/caddy-ct103-Caddyfile
2. Push to CT103: scp caddy-ct103-Caddyfile root@192.168.8.221:/tmp/ && ssh root@192.168.8.221 'pct push 103 /tmp/caddy-ct103-Caddyfile /etc/caddy/Caddyfile && pct exec 103 -- systemctl reload caddy'
3. Add the Cloudflare A record (script at /Users/bee/tmp-immich-stack/add-cf-records.sh handles multiple at once)
4. Run python3 /Users/bee/tmp-immich-stack/sync-bookmarks.py — or let the cron catch it within 6 hours

• Brave’s bookmark file is Chrome’s format — this same script works unchanged against Chrome/Chromium/Arc with only the path changed
• Brave assigns its own guid and checksum values on load, so the script doesn’t generate them — it lets Brave rebuild them
• IDs are allocated by scanning the entire JSON for the max existing ID and incrementing from there
• Timestamps use Chrome’s “microseconds since 1601-01-01 UTC” format — the script converts Unix epoch to this
• If you manually rearrange/delete items in the folder, the next sync run will wipe your changes and rebuild from the Caddyfile. The folder is machine-managed — use other bookmark folders for ad-hoc bookmarks