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Cannot Access Win11 Shared Folder on Android
(sh.itjust.works)
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My guess would then be probably Tailscale or Pihole somehow interfering with that connection for some reason. Idk if you're able (or willing) to remove those from the equation, but that might help narrow things down. If you have access to another computer locally, maybe sharing a folder on that and gradually adding steps to make it closer to your target system until it stops working?