Outlook 2016 and vpn

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.

lorenkjr said:

I have outlook 2016 which is a vpn machine. Anyway, I try add any other account expect a Microsoft Outlook account; It will not recognize the password. Is there any possible fix? If not could someone tell me if there is an email reader that works with vpn?

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.

You might try Thunderbird. Not a graphical but it generally works and doesn't require as much support. I don't use with VPN so I can't comment on that piece.

Caledon Ken said:

You might try Thunderbird. Not a graphical but it generally works and doesn't require as much support. I don't use with VPN so I can't comment on that piece.

I've been considering TBird myself, Ken; in fact, I have it installed, but haven't gotten a lot further than that.

Every new app/program presents its problems, and so far, I haven't whupped it into shape yet.

lorenkjr said:

Thanks I will look into that idea. I would have expected better from Outlook. Next time probably use free email. I appreciate your help.

On that front, I have also tried the free Outlook.com app that comes with Windows 10 and get the same results as with Outlook.

I have a good friend who's an Outlook MVP that I'm going to contact today and will see what I can find out from her.

Stay tuned for (hopefully) further news.

@lorenkjr @Caledon Ken

I went to Slipstick.com owned by Outlook MVP Diane Poremsky and found the below thread. So far, it's not a complete answer to our problem, but does give some hints, etc. to follow. I will go back and re-read it, since I mostly scanned to see if it would give us any help.

How to create a new email with @Outlook.com | Outlook Forums by Slipstick.com

Here's the link to all of the Outlook Forums:

Outlook Forums by Slipstick.com

Great.

Do you know Diane?

I'm a member there. I recommend that site when Outlook gets real cranky.

Caledon Ken said:

Great.

Do you know Diane?

I'm a member there. I recommend that site when Outlook gets real cranky.

Yes, I know her. Not on a face-to-face personal level, but on a fairly interactive co-beta tester level. IOW, we've worked together on a few things.