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

I have been doing fine with HotSpot Shield for about a month -- except now for the past five days it won't load many web pages and they say it's a known issue, though ironically it's continued to work absolutely perfectly all along with Outlook in Office 365 under Windows 7, when "almost" nothing else would.

I've now tried ExpressVPN with TCP and it took infinitely too long to load Outlook on multiple attempts so I stopped trying and gave up.

And I've now also tried PIA with TCP and I must say so far on two machines it's been working just fine with Outlook, with the only exception being it takes longer than normal to load Outlook but certainly not long enough to be a problem or be cause for concern.

For my money, I'll be staying with HotSpot Shield if they get this issue resolved of not loading many web pages and there's no issue revealed about their infrastructure having been compromised.

Windows 10 build 1803

THANK YOU. Both for identifying the fix, and for the step-by-step instructions on your blog. I shudder to think the time and risk you are saving us, to say nothing of the strain on data plans for those of us who've been over-relying on our personal phone hotspots.

This worked for me when none of the other solutions did. Thank you, thank you, thank you!

Well, I'm very glad so many here have resolved this. For the records, I'm still without a solution other than HotSpot Shield. I've tried most everything suggested here. The Mac Wheeler approach was also suggested to me by NordVPN tech support early on, until they eventually cited a forum thread showing many people who were never able to resolve this problem and told me it can't be done in my case.

And, to update my earlier post here saying PIA was working okay, it is not! It was for a time, but then, sure enough, hitting New email resulted in Not Responding for a very long time and essentially hung Outlook altogether, very similar to what I had been having with NordVPN previously.

It seems nothing using OpenVPN is working for me. I'm still running Windows 7, so maybe that's making the difference here, I don't know.

The only one that still works like a top for me with Outlook in Office 365 is HotSpot Shield -- although for a week now it's been having massive issues with not being able to load more than 50% of all websites, regardless of the country whose servers I choose, their tech support still acknowledges as a known issue and which I just have to assume is a massive undertaking for them to resolve and that they will be resolving it soon.