January 26, 2012

8 Comments

Microsoft Office 365 has been tremendously successful so far, certainly from a sales
perspective (millions of subscriptions, although the exact number is kept under wraps),
but more importantly its also been successful from a technical perspective. There has
been no downtime for the last few months. My clients are ecstatic that I can set
passwords not to expire. Smaller businesses are being migrated from the older Microsoft
Online Services platform; my clients experiences have not been completely smooth but
no data has been lost and support for minor glitches has been readily available. Life on
Office 365 is good.
So although Im going to describe a technical issue, its a fairly insignificant one that has
affected less than a dozen people in my personal experience. Its an interesting and
tricky problem!

Basically, at random times Outlook pops up a box and asks for the password for the
Office 365 account. Its usually when Outlook starts but occasionally happens in the
middle of the day. Most people find that checking the box to remember my credentials

makes the prompt disappear for days or weeks but others have it popping up
frequently, as often as every few minutes. (Again, to be clear, most people dont see
this at all. This isnt widespread.)
Take a peek under the hood to understand why its not supposed to do that.
The prior Microsoft service, Microsoft Online Services (aka Business Productivity Online
Suite, aka BPOS) installed the Microsoft Online Services Sign In program, which ran at
startup and displayed its little blue icon continuously down in the lower right corner. Its
job was to log each person into the service and keep them logged in through thick and
thin. When Outlook occasionally became confused and displayed the above password
prompt, no password would satisfy it. The only answer was to shut down Outlook
completely and sort things out with the sign in program.
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. To Microsofts eternal shame, the new
program has an almost identical name, Microsoft Online Services Sign-in Assistant,
apparently to make this as confusing as possible. You can imagine how much fun it is to
advise people what to uninstall when the list in Control Panel looks like this.

The new sign-in program runs completely unseen. Its job is to get the Office 365
credentials from a user when the program is installed, then provide them to the Office
365 service whenever they are required, all completely invisibly. Youre 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.
Outlook is a special case. As I understand it, the sign-in assistant does not interact with
Outlook. 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 dont know that for sure.

FIXES FOR PASSWORD PROMPTS

In the last couple of weeks Ive gotten more reports than usual from people being
prompted repeatedly for their Office 365 passwords. I dont yet know the entire answer
but Ive got some clues, and Ive been doing some magic dances that seem to help.
POSSIBLE UNDERLYING CAUSE: SERVER CHANGES
There is reason to suspect that Microsoft is moving Office 365 mailboxes from one
server to another behind the scenes. Thats meant to be completely hidden! Outlook is
automatically updated with new server names deep in the mailbox settings. We dont
care whether the Microsoft server is named ch1prd0404.outlook.com or
pod51009.outlook.com.
In one perceptive forum message, though, WhiteKnight 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. Either Microsoft is making more changes than expected as they balance out the
Office 365 load, or theres an error in the way the servers are set up that causes them
to challenge users too often.
POSSIBLE FIX NO. 1: INSTALL OFFICE UPDATES
In my experience, the repeated password prompts are happening far more often with
Outlook 2007 than with Outlook 2010. In many cases the most recent service pack has
not been installed. Office 2007 Service Pack 3 is pushed as an Important update but not
automatically installed. Its a huge download and slow to install and frequently requires
a system restart.
A couple of days ago another update began to be pushed as an Important update,
called Update Rollup for Microsoft Online Services Sign-In Assistant. The KB article
describes users being repeatedly prompted for credentials. Looking deeper into it
makes me think that the update actually addresses a completely different problem and
does not affect Outlook but its a striking coincidence that an update for the Sign In
Assistant appeared at exactly the moment that I was looking for it.

POSSIBLE FIX NO. 2: SAVE CREDENTIALS AT THE OFFICE 365 PORTAL

Each time Ive gone to the Office 365 portal on the desktop of a user being prompted by
Outlook, Ive been prompted to put in the Office 365 password.

As I understand it, though, that prompt isnt supposed to appear. The sign-in assistant is
supposed to be providing the credentials so the portal is displayed immediately.
Click below the name where it says Sign in with a different user ID. Now you can sign
in and check the box to memorize the password again (Keep me signed in).

Again, this shouldnt change Outlooks behavior. Its unrelated. It seems to help! Maybe
its a placebo effect.
POSSIBLE FIX NO. 3: LOOK THROUGH WINDOWS CREDENTIALS
Windows 7 has an interesting Credential Manager. (Type in credentials in the upper
right corner of Control Panel.) Vista has a rudimentary version of the same thing look
in User Accounts for Manage Your Network Passwords.

My list above has a number of names that include RED001. Thats the indicator of the
old Microsoft Online Services, since my mailboxes have not yet been migrated to Office
365.
After the migration, all the references to RED001 should disappear and be replaced with
servers named xxxxxxx.outlook.com, the Office 365 servers. In one case I was able to
remove an old RED001 entry here and stop a persistent password prompt. In two other
cases Ive got Outlook prompting for the old RED001 server password even though the
migration to Office 365 happened months ago and all local references and DNS entries
have been thoroughly scrubbed.
After that, well, Im out of ideas. If you find a fix to the pestering password problem that
I havent mentioned, let me know!