Outlook: Cannot open this item. Outlook has already begun transmitting this message

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We had a strange one this morning:


A couple of messages were stuck in the Outbox.

This site has some good troubleshooting tips:

However, after running through all of the steps Outlook eventually did step up and send the messages. Though, that happened when Outlook was _in_ Offline Mode.

It turns out that we now know why the Send/Receive process is being hung up:


Our Office 365 account was stuck?


Apparently there were no issues? Hmmm…

We tried to add the O365 account to a different system’s Outlook and we hit this:


Using Men&Mice’s awesome freebie online DIG tool we checked to make sure that AutoDiscover was indeed set up (which it was when we configured things back when).


So, at least at this point it is looking like the service is indeed having an issue.

And finally, after a huge pause Outlook’s Send/Receive coughed up an error:


With the volume of e-mail we have flowing about right now having Outlook getting hung up on one of the mailboxes during Send/Receive is outright frustrating! :S

We removed the O365 account and sure enough Outlook has started sending and receiving without a hiccup.

Philip Elder
Microsoft Small Business Specialists
Co-Author: SBS 2008 Blueprint Book

Chef de partie in the SMBKitchen
Find out more at

Windows Live Writer

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