Windows 10: Outlook Keeps Asking for Password

Not there. *Banghead

 

Yep, that's pretty much a given, Ken.

I've opened a ticket with Windscribe, so we'll see where that leads me.

No masks that I know of, and I'm not sure about a logging tool. Simrick uses WS, so maybe she'll know. I do know they erase everything three minutes after a session ends.

 

Wynona, try to access Outlook with Windscribe's firewall set to off . It won't hurt your privacy. This is just in case your PC turns off and would reveal your real IP address to outside world, before windscibe kicks in...

This would eliminate one unknown...

@Wynona: while browsing MS forums I stumbled against one topic, similar to yours. While it won't show you any useful direction to solve your problem, it'll let you know, that you're not alone with it, and it may even give you a chance to smile (bitter sweet).

 

The problem is the Windscribe cert doesn't load into Outlook, probably because she's using Insider O365. It works if she shuts the "whole computer" VPN off, and only uses the browser extension. Tech support have to help her get the cert loaded properly into the Outlook email client. They also need to be made aware that this is a problem in Office Insider.





She does not have this cert showing in her client, and it needs to be there.

 

Simrick, and it's working with @ hotmail and @ live.... Don't think that's the main problem. Something on the outlook.com side have its share (or combination)

There are about 10 to 15 possible different reasons for such behavior (regarding to quick analysis). Some of them are fixed in latest version (1710)

Do you have the latest (stable) version Wynona?