Office 365 cloud features do not work when using a privacy VPN

Windows 10 1803, Private Internet Access (PIA) using their app, Office365 Personal, OneNote desktop version.

Notable: For part of the time I was connected, Windows was showing the warning symbol on the Network icon and hovering showed I was connected but "No Internet Access" on both - browsers worked fine, OneNote did not.

I tried switching from UDP to TCP in the advanced settings, and that didn't seem to make any real difference. However, at some point in there Windows started to see an Internet connection, and at that point OneNote was able to sync. I've since changed back to UDP and it's still syncing correctly.

Edit: after a quick experiment, it seems like what made a difference was disconnecting the VPN, getting OneNote to authenticate (clicking on my name and waiting for the generic person icon to change to my initials), then reconnecting to the VPN. After that, I was able to force a notebook sync even with the VPN connected.

On a technical basis, I'm wondering if something about this is similar to an issue early on with Windows Subsystem for Linux - it was pulling incorrect DNS servers from the registry and populating those into the Linux instance, so Linux wasn't able to properly connect to the Internet. (https://github.com/Microsoft/WSL/issues/2694) Is something about the network detection pulling information about an incorrect network interface and all the disconnecting, changing parameters and VPNs and reconnecting just sometimes causing it to change which interface it grabs first?

I have the same problem, can't save when connected via my Cisco VPN, this is a **** Microsoft Office 365/One Drive crapware problem.

Hi all,

Came across the thread as I was having the same issue with NordVPN: Office365 wouldn't recognise it was connected to the internet when the VPN was active, and OneDrive wouldn't sync either. Tried the TCP/CyberSec thing and no luck for me.

Then I came across this article:

https://www.macwheeler.com/windows-10-office-365-cannot-connect-over-openvpn-fixed/

which seems to have fixed it for me.

BUT...I have a question as to whether there are any security issues or similar in using this solution?

Thanks all.

Hi,

Indeed it seems that adding a default gateway of some kind is what's required.

In terms of your question I'm no security expert though I'd have thought a VPN is secure by nature coupled with all traffic being encrypted already.

I use NordVPN and Office 365. I found that the instructions at the below URL worked. In summary, go to your TAP Ethernet adapter and while maintaining DHCP, click the advanced button and add your local network gateway to the list.

https://www.macwheeler.com/windows-10-office-365-cannot-connect-over-openvpn-fixed/