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

I finally got around to coming up with a fix for Offece365 and OPenVPN problems, I have published a guide to fixing these problems here:

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

Hi all

This is my first time on this blog.  I too have had problems with Microsoft and PIA.  Two topics:

1. For a while I could not send emails from Outlook 2016 (with PIA connected).  PIA told me that they were going through a whitelisting process that would take some time (as I understand it, making sure all the big name email providers, eg google, yahoo etc) work with PIA.  Well that process DID take some time but now I am fine.  Apparently its all to do with SMTP etc.  I am a novice so apologies if this seems unclear. Bottom line though is for me at least I can (now again) use PIA when sending emails from Outlook 2016.
2. Login and auto save with Microsoft Onenote and Word.  Like many in this blog I too found I could not login/autosave etc with PIA connected (altough I should say that I used to be able to do so; things just stopped working on that for me a month or so ago).  Anyway, I just wanted to add my comment that I changed from UDP to TCP and all is fine again for me.  As I novice I have no idea of what TCP and UDP are or mean so I have today asked PIA to explain if there is any reason I should not change my default PIA setting from UDP to TCP (eg privacy integrity??).  

So my fingers are crossed that both of my above problems are now solved.  I see that others in this blog have found the Microsoft autosync problem re-emerge.  I hope that doesn't happen to me....but we will see.

Good luck to all with either or both of the above problems.  I hope my comments helped a bit.

Hi,

Outlook 365 will connect for me when using U.S. server(s) but when I use the Canadian server(s) (to be able to connect to Amazon, which is a whole other issue) I cannot login to Outlook.  I haven't tried to use any other servers (I live in the U.S.). This is really starting to be a pain as I prefer to use Outlook email client and do not care for webmail clients (GMail, etc.).

Just reporting back that I've had only limited success with adding the DNS manually.  In the end I gave up and contacted NordVPN support.  They don't have a fix but they at least told me why Office products think I am offline:

https://blogs.technet.microsoft.com/the_microsoft_excel_support_team_blog/2014/03/24/office-2013-reports-no-internet-connectivity-with-vpn-connection/

As I just mentioned they said they didn't have a fix but they said they are working on it.  We will see.  Microsoft seem to have come up with a very clunky way of testing for an internet connection, hopefully they will come up with a better solution.