Dropbox and VPN Issue. Won't upload files when VPN is disconnected.

Hey there!

Sorry for the late response - are you still having issues?

I have the same problem in Mac OS X, when the Dropbox is syncing I lost the VPN connection.

i've been running private internet access vpn for a couple of years, no problem.. in the last week, dropbox has stopped connecting when the VPN is turned on. any suggestions on a way around this?

I am having the same VPN related issue.  Startup laptop (Win 7), dropbox is syncing fine.  Connect to work VPN, dropbox is syncing fine.  Disconnect from work VPN, dropbox is not syncing.  Pause and resume, no luck.  Exit dropbox and restart, still no luck.  Reboot laptop, dropbox is now syncing. Very annoying.

I have the same problem on OS X. Dropbox is working fine with the OpenVPN client (which is set to tunnel all network traffic), until the computer enters standby and VPN client disconnects. When resuming from standby, Dropbox is no longer connected and will not connect, regardless of VPN status.

If I "pkill -9 Dropbox" and restart it, it works fine again.

I presume Dropbox is initiating some connections outside the VPN (or rather VPN connection is established only after Dropbox connects), so after wake-up Dropbox connections no longer works.

Unrelated, Dropbox leaves a lot of connections in CLOSE_WAIT state - "lsof -i4tcp | grep Dropbox" consistently shows ~10 Dropbox connections left unclosed.

I'm having the opposite issue. Dropbox only syncs when my VPN is disconnected. Other Internet access is uninterrupted. Any ideas?

It seems Dropbox remains in a "Connecting" state indefinitely whenever the traffic switches between the network adapters (VPN is turned off or on). One workaround I found is to manually pause and resume syncing, from the quick menu. It fixes the problem every time, annoying as it is.

Same issue. Dropbox was syncing fine with PIA enabled until a couple weeks ago. Beginning around the time I did the El Capitan OS X upgrade I think it got wonky. Now I have to disconnect the VPN and kill/restart Dropbox to get it to sync. Anyone have any ideas? 

Is your Vpn compression set to on? Dropbox may notice that ALL local files are reading with a distinct variation that can't be . I'd hope dropbox would test this if given the suspicion, maybe by checking if what is sent down to you is not matching bit for bit when uploaded a moment later. I'd hate to have compressed originals or compressed updates destroying the database

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