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The default tor downloader for me never works. I always have to end up manually installing. Is this normal? Or a sign that I'm compromised? thank you

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Not normal, but also not a sign for being compromised. See:

Am I compromised?

Debugging your tb-updater issue is not suited for stackexchange, because'd have to provide debug output, answer back and forth several times. If you want to like this out, please post in https://forums.whonix.org.

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