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From Google Drive to Syncthing over Tailscale

By · Published by Everything Blog

In short

The transition was necessitated by sync errors between desktop and iOS password clients caused by how Google Drive handles file identifiers during saves. While Syncthing manages decentralized file distribution, its default mode uses public discovery and relay servers that expose network addresses to outside parties. Routing this peer-to-peer traffic through an encrypted Tailscale mesh network successfully eliminates the reliance on those public relays. A dedicated Synology NAS functions as the central hub in a star topology to maintain seamless updates across the user's laptop, iPhone, and iPad.

Key points

  • Routing peer-to-peer traffic over a private Tailscale network removes the privacy risks a…: Routing peer-to-peer traffic over a private Tailscale network removes the privacy risks associated with public relays.
  • Migrating away from corporate cloud storage prevents full version histories of sensitive…: Migrating away from corporate cloud storage prevents full version histories of sensitive databases from accumulating on external servers.
  • The open-source Headscale project provides a viable self-hosted alternative if complete i…: The open-source Headscale project provides a viable self-hosted alternative if complete independence from Tailscale coordination servers is needed.

Sources checked by our analysis pipeline: 1

I used Dropbox for decades, then switched to Google Drive. Both worked for most of my files. One file never fit, though: my KeePass password database. It’s the file I need on every device and the file I want to keep private the most. After one annoyance too many, I moved it to Syncthing over Tailscale. The rest stays on Google Drive, for now. This post describes why and how.

The file that made me care

My password manager is KeePass-based.

I use KeePassXC on my laptop and KeePassium on my iPhone and iPad.

Both open the same .kdbx

file.

The file is a single encrypted binary, written as a whole on every change and protected with a physical security key.

I edit it on any device, sometimes offline.

That’s the worst case for any sync tool.

In my original setting, Google Drive was the proxy between my laptop and my phone. I bought the KeePassium premium tier for its Google Drive integration. The setup was dead easy, and it worked. However, now and then, the copy on my iPhone…

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