Office 365 And Outlook “Trying To Connect”

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Microsoft has been upgrading Office 365 subscribers to new servers during 2013, with improved webmail and a completely overhauled dashboard for users and the latest versions of Exchange Server and other server platforms on the back end. The upgrades haven’t all gone completely smoothly but it seemed like good news all around once the migration was complete.

For more than a month, though, Outlook users have been dealing with connection issues. Every so often, Outlook will switch from “Connected” to “Trying To Connect” and sit there helpless for a while – anywhere from a few minutes to several hours.

The reports I got were sporadic and scattered. It would hit one person in a business, but not everyone on the same subscription; a week would go by without any reports, then two or three people would contact me about it. I tried a variety of troubleshooting tips – toggling Outlook’s “work offline” switch, or repairing the email account in Control Panel, or creating a new mail profile. Occasionally one of those would seem to work, although now I think that was a coincidence and Outlook would have reconnected by itself.

It turns out there has been an ongoing problem with Microsoft’s servers that has caused the problem. This is the most active forum thread about the disconnects, with the first post from Microsoft tech support on June 28:

“We are actively investigating intermittent connectivity issues that are affecting some Outlook users on our Office 365 service. The symptoms of this problem are the "Trying to Connect" or "Not Connected" messages reported by the Outlook client. The issue is intermittent and, in most cases, is automatically resolved within a few minutes.”

Since then, there have been updates every few days with no details, but filled with promises that engineers are installing updates and working on fixes “diligently” and “with the highest priority” and “as if their lives depended on it.” There are also several hundred comments from angry users and IT support people who can’t believe this has been going on so long.

They haven’t fixed it yet. It’s better, but they haven’t fixed it yet. Until this is finally fixed, you might still have Outlook occasionally lose its connection to the Exchange server. There’s no way to guess if it will be over tomorrow or next month.

This too shall pass. Outages happen.

Three things to keep in mind.

  –  This isn’t happening very often. Most people are not ever having this problem.

  –  Use webmail if you need to while Outlook is disconnected. Outlook Web App is not affected by this bug.

  –  Outlook will reconnect by itself. Don’t go nuts trying to do repairs. The problem is not at your end.

I’ve had no reports and no personal experience with the problem this week. I’m crossing my fingers that we’re near the end of it. Let me know if I can help by commiserating or sounding guilty if it happens to you.