Action required: Upgrade Tailscale to 1.14.4+ prior to updating Windows
Blog post from Tailscale
Users running Tailscale on Windows 10 or Windows 11 need to upgrade to Tailscale version 1.14.4 or later before performing a Windows Update to avoid losing connectivity to their tailnet. This issue arises because previous Tailscale versions stored critical state information in a directory that Windows updates can wipe, resulting in the loss of essential files, including machine keys. This necessitates re-registering and re-authenticating machines to regain network access. Tailscale 1.14.4 has addressed this by changing the storage location to a more stable directory, and affected users can verify their machines through the admin console or contact support for assistance if connectivity issues arise post-update.
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