To Microsoft’s eternal shame, the new program has an almost identical name, “Microsoft Online Services Sign-in Assistant,” apparently to make this as confusing as possible.
Instead, Outlook relies on its built-in ability to memorize credentials (assisted by Windows).
My gut tells me something is done on the server side as well to avoid challenging Outlook very often but I don’t know that for sure.
That was never clearly understood by end users so Microsoft reworked the process for Office 365.
A different program is installed for Office 365 and the old sign in program is removed.
In one perceptive forum message, though, “White Knight” found that every time one of his users was prompted for a password, the underlying server had changed for the mailbox.
He reports Office 365 mailboxes that have gone through seven different servers.
You’re not supposed to have to put your Office 365 password when you click into the Office 365 portal or Outlook Web Access or Sharepoint portal.
Behind the scenes the sign-in assistant is taking care of that for you. As I understand it, the sign-in assistant does not interact with Outlook.
(Again, to be clear, most people don’t see this at all.
This isn’t widespread.) Take a peek under the hood to understand why it’s not supposed to do that.
It’s usually when Outlook starts but occasionally happens in the middle of the day.