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Dropbox "Connecting..." with VPN

Been using Dropbox for many years. Normally DB is connected and status is "up to date". And it had been then when I started VPN to the office, that DB would lose connection (not surprising) and would then re-establish the connection. But for the past few updates, the DB icon in the tray is grayed out and the status stays "Connecting...". Sometimes it will even sync any changes that get made (say I upload a picture via my phone), but not always. Proxy is set to AUTO.

Definitely didn't have this problem in earlier versions - just not sure exactly when it started (currently running v127.4.4265 on Windows).

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dhayduk

Oh, should have mentioned that if I disconnect from the VPN, then Dropbox will successfully connect after a few seconds.

Also, if VPN is connected and I completely kill dropbox and restart - then it will connect successfully. But then when I disconnect VPN, it will stay in "Connecting..." mode.

So basically, it doesn't like having the network endpoint changed while it is running (and doesn't seem to actually retry the connection)...

Megan

Hi @dhayduk, how are you today?

Sorry to hear about this issue - can you try locating the Dropbox icon and menu from the system tray ?

Then, try right-clicking on the icon to access the Dropbox desktop application menu and click on the gear icon in the Notifications panel.

Select "Preferences" from the Dropbox menu. Select the "Proxies" submenu or tab and from there "No proxy".

Can you give it a go, and let me know how it goes?

dhayduk

I changed to "No Proxy" but Dropbox still didn't connect (we do use proxies at VPN, so that's why I've used auto-detect in the past and it correctly detected "no proxy" when off VPN and "proxy" when on VPN)...

I did notice this morning that Dropbox had connected overnight. Hours after the initial VPN gets established - Dropbox is finally able to connect.

I'll check again tomorrow (VPN connect gets reset every 24 hours; currently connected for 4.2 hours).

Megan

Happy Monday @dhayduk!

I'm here to check how things are for you now. Could you also check your DNS settings?

Also, feel free to let me know your ISP location, please.

Vas V.

I am also having issues with dropbox refusing to connect while a VPN is active. This started up within the last month, when I switched AVG VPN from OpenVPN to Mimic VPN protocols. I have to exit the application and re-launch it to connect, but if the net goes out at any point, the application can't reconnect till it has been restarted.

dhayduk

Yeap - exit and relaunch does allow the connection to succeed. So it is just something about connection being twiddled while Dropbox is running...

alturic

After 2 years, nothing has been fixed with this issue?

Jay

Hi @alturic, according to our info, there isn't an issue as such, since we would have many reports of the same nature.

Does your VPN have any settings that could be restricting traffic to the following Dropbox domains?

dhayduk

I'm still seeing this with 181.4.5678.

Boot computer and dropbox connects. Start VPN and dropbox is stuck in "syncing" (next local change just stays at "uploading" forever). Restart dropbox and everything is happy. Disconnect VPN and dropbox gets stuck in "syncing" again.

dhayduk

And "pausing" and then resuming syncing doesn't fix it either.

Sometimes I can toggle the proxy setting from auto to direct and then back to auto and then it might work. But that's successful maybe 30-50% of the time and so I usually just restart dropbox entirely.

alturic

Yep, exact same problem here.

Using OpenVPN.

alturic

@Jay Thoughts?

Conditions to reproduce

Be connected to OpenVPN (unsure if this affects other VPNs or not)

Be connected to DropBox

Lose Connection/Reconnect to VPN

DropBox loses internet connection and never regains it.

In my case, it's even crazier DropBox thinks it lost connection to the internet because I don't use my VPN connection for any internet traffic outside of connecting to corporate servers. Pausing/unpausing does nothing, I have to close DropBox and reopen it and it's happy again.

Megan

Hi @alturic, I hope you're doing well!

A VPN can cause issues with the connection of the desktop app, one way or another. Maybe not at first, but initially it will.

Now, connection problems usually mean there is a proxy, firewall, antivirus or other type of security program in the way. Can you check that?

Moving forward, the best way for you to get assistance might be to reach out to the company that makes your VPN for support, and ask them about this too.

alturic

Megan,

I don’t believe my ISP or VPN provider can tell us why Dropbox loses connection when connecting to a VPN (although as a developer I can understand vaguely why) NOR would they be able to tell me why Dropbox can never reconnect after it loses connection, outside of closing and reopening Dropbox.

We’ve provided reproducible steps on how your team can track down why Dropbox has this issue, so we will have to wait until Dropbox provides a fix.

JP25

I have the same issue and use ProtonVPN. Dropbox icon remains grayed out until I restart the app or disable VPN.

alturic

Still no resolution to such a simple issue. Sad. I prefer DropBox to all of the other file management solutions out there too - all of which work completely fine with connecting/disconnecting to VPNs.

And again, in my situation, my VPN is strictly routing a few IP's through it. Anything and everything related to DropBox is always routed through the default LAN connection.

AtlasJustice

I have this issue. Using ProtonVPN. Annoying that i have to restart Dropbox on my Mac. Disruptive when i forget to manually restart Dropbox and then my local files don't sync with my partners. Please fix!

alturic

You know, I came here to give an update about how I thought it was a specific provider I was trying out at the time, but after reading my comments I was (and still am) using OpenVPN and while I am using the OpenVPN GUI and not their normal app (which is what I was using at the time), I haven't had this issue since.

So it's possibly it's something with the way the actual underlying "app" that performs the connections is doing. I'd suspect that some of the apps (unless they all inherently have to of course) potentially cut all connectivity when it connects/reconnects and that trips up Dropbox.

Like I said, I'm currently using OpenVPN GUI and I haven't had the issue with Dropbox since. Absolutely nothing else has changed on my end since.