Apple iCloud Safari Private Relay causes socket timeouts

The web interface seems to work fine but trying to connect with the SeaFile Client for Mac failes after a minute with a connection error and a complaint about sockets. Turning off Safari Private Relay in System Preferences → iCloud immediately restores fixes the problem.

I lost way too much time on this after turning on Safari Private Relay on Monterey, not noticing till much later that the SeaFile client was not connected, and not putting the two together until after looking in all the wrong places. Hope this post saves someone else from the same frustrating experience.

I found this thread trying to resolve my own issue, but perhaps it’s related to yours. With Private Relay turned on, I cannot access any HTTP (as opposed to HTTPS) site in browsers other than Safari. For example, I can’t use firefox to go to Google with “http://”, while “https://” works just fine. I get the same behavior when I try to use the curl command line client. Oddly, other friends with Monterey and Safari Relay turned on do not get this behavior, so who knows.

Maybe SeaFile is making an HTTP connection somewhere under the covers?

Thanks Zlexi, I believe you are correct! I hadn’t installed my ssl certificate at the time I wrote the original post so was using http, but now I have and everything seems fine when I turn on Private Relay and connect via https.