You push a newer image to your registry, Watchtower wakes up on schedule, scans, reports a clean run — and your container keeps serving last week's image. No error, no restart loop, nothing red to chase. It just silently stops recreating. If that started happening around the time you landed on Docker 29, you've found the cause.
The classic containrrr/watchtower image — the one in basically every tutorial — is effectively unmaintained, with its last release back in 2023. It's a Docker API client, and when the Engine's API moved forward, the part that lists and compares images kept working while the part that actually recreates containers quietly fell off. So you get the worst failure mode there is: a tool that reports success while doing nothing.
The fix is a one-line image swap to the maintained community fork, nickfedor/watchtower:latest — a drop-in replacement with the same labels and env vars that tracks the current Docker Engine. On my Docker 29.2.1 box it recreates cleanly again (scanned=10 updated=1 failed=0), and I let homelab-monitor surface every recreate by its reset uptime — so I can see which container the auto-updater just touched, and get a push alert if a recreate ever comes up unhealthy.
The full guide has the exact compose, the bring-up commands, the real recreate log lines, and how to opt containers in safely with the label.
Read the full guide on Medium → https://medium.com/@arsen.apostolov/how-to-fix-watchtower-not-updating-containers-on-docker-29-a891217c6db2
