Windows 10: Outlook 2016 and vpn

Thanks everyone. I will give Thunderbird a try. This seems like a pretty sticky problem. But who knows, as will try the outlook suggestions too.

Wynona said:

I have Outlook 2016 also, Loren, and have the same problem you do. I have a lifetime subscription to VPN Unlimited, and had that problem. So, I "dumped" it and got a lifetime subscription to Windscribe. Same thing happened with Windscribe too, so it's obviously a failing with Outlook, but so far, I haven't seen a solution to the problem itself.

Fact: I have installed Windscribe on my desktop computer and in the browsers I use; Firefox and Chrome. I haven't tried to install it in Edge yet, because I only test when a new Windows Insider Program Build is released.

The one workaround I have found so far is that I can turn the desktop version of Windscribe off, run Outlook and get my emails. Another thing I have found is that the desktop version of Windscribe doesn't seem to email addresses I had before, such as at Hotmail, at live.com, etc. Just the ones at outlook.com.

Wynona, I went to gmail settings for legacy, turned that on and what do you know; it now works gmail. Now if only I find legacy settings for the other two.

Caledon Ken said:

Hi lorenkjr. Welcome to the TenForums @lorenkjr

Very similar problem as this one.

Outlook Keeps Asking for Password

I would contact the VPN supplier and investigate whether a Certificate has to loaded in Outlook to work.

Thanks Ken, I went to gmail settings for legacy, turned it on and it now works for gmail only. I am still instigating the other two.

I found the answer, you need to turn on legacy apps in gmail. Sorry I do not have link but, I can now do gmail. Don't have the other two yet but, I will continue searching.