My macOS Dropbox desktop app is stuck "reconnecting".

Hi NoteWriter​ and welcome back to the Dropbox Community! I’m so pleased to hear your Dropbox app is finally reconnected and thank you for coming back to share your update. It’s always helpful when someone follows up, especially with trickier Mac connection issues like this ✨.

I’m Theresa 👩‍💻, one of the Community Managers here. Now that everything’s up and running again, I’d love to know... do you have a favourite Dropbox feature that helps you stay organised or makes your Mac experience smoother?

Looking forward to hearing from you,

T 😺 (Dropbox Community Manager)

Hi from me as well, NoteWriter! In general, the desktop app should be automatically updated to the latest version indeed. 

In case you face similar issues in the future (especially after the next app version is released), please let us know and we’ll investigate this further.

Yes, this helped. 

Any idea why wasn't the app updating itself to the latest version automatically? I've found no "Check for updates" button anywhere.

Thanks!

Actually, the issue seems to be about iCloud Private Relay. 

Since this has never been a problem before, it can only be that a recent update to the Dropbox app doesn't like that. I will stop using the Dropbox desktop app until I receive news that this has been solved. 

I'm sorry but I will not downgrade the security of my internet connection just to use this app.

Hey NoteWriter, thanks for the heads up! 

I was also going to suggest that you try signing out of the app and then sign back in. You can follow these steps in order to achieve that. 

Uninstalling the app isn't necessary for the time being, but if you want to go for it you can always see the steps here. 

Let me know if this helps! 

Hey Megan, thank you for your prompt reply.

It has been a couple of days, maximum a week. I've just checked on the website version of Dropbox and the file has been correctly uploaded there. It seems just to be the app that is staying greyed out in the macOS menu bar. 

I have no VPN (apart from iCloud Private Relay, but that has never caused any issue to Dropbox so far), no 3rd-party antivirus and no ISP/router settings that I could be aware of (it is using the factory settings and then I am using a public DNS (Cloudflare)). 

Internet is globally working perfectly fine, with only Dropbox exhibiting any issue. Is there any log I could share or something else that could help diagnose? Or perhaps log-out / log-in from within the app? Uninstalling / reinstalling?

Thank you!

Hey NoteWriter​, let's jump right into this! 

How long has the app been like that?

Did you make sure that this is not caused by a security software on your computer or your network settings? Do you have any proxy, VPN, security software, or even ISP/router settings that could be restricting traffic to the following Dropbox domains?

Also, it might sound trivial but have you tried restarting your modem/ internet router by any chance?

Let me know more, and we'll take it from there!