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Since my workplace introduced HTTPS traffic inspection as a security measure, the Dropbox client on my Ubuntu machine doesn't synchronize anymore. It doesn't, however, display an error message, instead it will forever say "Syncing n files..." without any progress.

I've installed the CA certificates, browser and other services run fine, it seems that the Dropbox client is affected selectively.

Some googling tells me that Dropbox uses Certificate pinning, which is incompatible with HTTPs inspection, meaning there won't be a way to get syncing to work. Is that still the case (the latest sources I could find were a few years old), and/or are there any ways to resolve the problem?

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  • The simplest case would be to throw these Ubuntu machines in their own VLAN, and exclude them, from the HTTPS inspection process. I am guessing that isn't a solution. What solution did your IT Administrator give you?
    – Ramhound
    Commented Nov 6, 2023 at 22:53

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