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I have a Windows 7 computer at home with Outlook 2010... I have outlook working with my office 365 account, however each time I login the "Windows Security" box comes up and I'm prompted for my password. I do have the Sign on Assistant installed. On the Windows Security box, if I do click "Remember my credentails" it will not prompt me for my password.
I don't think this is the correct way for the Sign On Assistant to work is it?
Before moving on, I would like to confirm the current situation.
You have installed Microsoft Online Sign-In Assistant and connect Outlook 2010 to the Office 365 account. When you open Outlook 2010 each time, the prompt message about typing credential occurs until you check “Remember my credentials” box. Is it correct?
Moreover, does this issue persist now when you login each time after restart Outlook 2010 or rebooting computer?
From my understanding, No. It makes sense. Microsoft Online Sign-In Assistant is mainly to allow common applications, such as Microsoft Outlook and Lync, to authenticate to Microsoft Online Services.
For detailed information about Microsoft Online Services Sign-In Assistant, please refer to Overview section of the following link.
I'm writing to follow up my previous reply.
If you need further assistant on this issue, please feel free to post back.