Windows security asks user login and password for Outlook repeatedly

This problem has reached a critical point. I have spoken with several MS techs and gotten nowhere. I am hoping for a miracle that maybe someone here has seen this before and has an idea I have not yet tried.

The User has a Surface Pro 4. Windows 10 Pro OS, Office 365 with all the latest Updates.
The only thing that is not 100% as it should be is that she uses a local account rather than a Microsoft account on the system. But it has been this way for years and only in the past 4 or 5 months have things gotten so far out of hand.

It has finally reached the point where the Login Box for Outlook will come up if she goes from her home to the office. For a while it was something that only occurred when she traveled. Hotels, airports, etc. But now it is almost a daily occurrence if the laptop changes from one network to another.
I have tried removing all the Windows generic credentials but while they do recreate for Outlook, they don't fix the problem

The worst times are when it refuses to accept even her correct Outlook Password. This often happens and she is forced to use the Web Portal version of Office which Always seems to work fine. No problems with passwords there. Only when she uses Desktop Outlook (which is what she prefers to use)

If anyone has any suggestions, I would appreciate hearing them. I thought i had already tried everything out there but maybe there is one i don't know about yet.

It has crossed my mind that MAYBE MS is creating the problem because she doesn't want to use a Windows Account on her system. She prefers to stay with a Local Account only on the system. Could it be that simple? Just because she is not using a MS Account on a MS Surface Pro.

Or Maybe the Windows Security center that runs under Windows 10 Pro works differently that under Windows Home. Only this one person in our company has this problem and of course, she is the owner,

Hi to all. I am glad i waited for all the comments. So: Others had this happen too? And a LOT?
I spent the whole weekend just now with that Surface Pro and about wish I had never seen one.
If you want to find out MORE than you really want to know, try the latest version MS Support and recovery Assistant (SARA).

Choose the Advanced option for All of Outlook and you will find out every tiny quirk about Outlook Except For: The answer to the problem. Tons of places in the registry that might be off by a tweak or missing shortcuts or you name it. But nothing that specifically ties to anything that could cause this Odd behavior. I am starting to believe it is an issue where the system loses contact with the Microsoft exchange servers and cannot find its way back to the correct server. In other words, a problem with the "auto-discover" routines in some way.

As this ONLY happens to this one person and She happens to have a Surface Pro, i began looking at how that might tie in. To the one person (I believe it was Captain?) who responded they had that same problem for a while do you mind telling me if you had either a surface Pro or another system with a Marvell Avastar WiFi chip-set? The only other possibility is the version of windows on a Surface Pro is Windows 10 Pro.

She does Not have or use MFA for those who asked, Nothing Multi- Login or anything not 100% plain vanilla. Same as all the other employees. I have checked all the normal things and many Abnormal ones but this has almost become a problem with her name on it. The Marvell Wi-Fi is used on almost all Surface Pro and other Surface laptops. It was widely reported last month that the firmware i this chip had been the subject of a widely announced 'Bug' so i am wondering now about that.

If her WiFi connection is unstable and causes the auto-discover routines to lose contact with the correct exchange server, this is pretty much what one would expect to happen. I also found out today that i can let the system sit for a while and the connection to the MS Exchange servers will finally "fix itself". I wish she had a Dell like everyone else.

Nice Try Calendon Ken. But .. a few small problems with it.

1: She already pulled that off a few months back. Microsoft offered a swap on almost every SP4 sold to anyone who complained about the "Screen wiggle" issue.
The one she has is technically only 4 months old. And to be honest, I am on thin ground blaming the Wi-Fi chip at this point. I am just grasping at straws!
2: Her Original purchase is now well past any kind of warranty. The "screen jiggle" effect was one exception where MS allowed almost anyone to get an exchange.


I think she should just get a new laptop and this time go with Anything But a MS product. Vote with your wallet. Works every time. I am not a big fan of Dell but I swear every other system we have is a Dell and it seems they never have issues like this.

By the way, all the time spent with the SARA tool apparently DID do some good. She isn't having the problem nearly as much now but it COULD be that MS exchange server was having hiccups and got better ?

No. And deeper into the rabbit Hole I go.

Here is the latest offering i can give. I’m pretty close to proving the case but not quite there.
I read that Microsoft Office on the Web has recently starting using Direct-connect as its main connection method. And as a “coincidence” Office web-portal ALWAYS works on these systems. In addition, their cellphones or iPad etc. (which also don't use Auto-discover) also always work.

Only devices that would be using the "auto-discover" services of windows 10 will fail.
I have found numerous reports about cases where it appears that the Direct Connect features used by the Web-portal service can cause problems with windows auto-detect.
The problem with this idea is that the only working solution i have found is to allow the systems to connect to the web-portal copy of office First. And Then try to connect the desktop version. In almost every case, this appears to solve he connection issue.

Office 365 Desktop only uses Auto-discover which was already my prime suspect in this issue.
The Marvell chip-set used in Surface Pro laptops is unstable at best, Unreliable much of the time.
The two people who have this problem BOTH have a surface pro.
Out of 40+ employees, no one else has a surface pro and no one else has this problem.
The problems only occur when the users are in unusual locations such as airports or hotels.
Never as far as i can remember when they were either at home or at the office.
BUT
There is ONE exception: If they have been on the road, when they first come back to the office or home
they sometimes do have it. But once they connect to their local networks the problem is gone and does not recur until they leave again, And these two spend more time on the road(in the air) then they do at home by far.

If they then go out to eat or elsewhere even locally where they are required to connect to a public WiFi, the problem recurs,