I’ve been working on a case with Microsoft’s Office365 support for several weeks trying to find out why email sent *to* a particular user was not being journalled. All the other mail seemed to be journalled to the external recipient, email from the user was working, just not email to that user.

The experience was quite frustrating as Microsoft’s support were terrible at calling back and could not grasp the concept of email tracking. Their solution after making a change was to wait a day to see if it was fixed although it was quite apparent that the Microsoft servers were not even trying to send the email (by looking at the Trace Logs you can see what email was being sent and received).

After checking the connectors were setup, mail properly scoped, the user had no rules on their mailbox, Microsoft’s solution was to delete the mailbox and reset it up again.  Not so easy when the mailbox/user is federated with Active Directory and the user happens to be the owner of the company. That was not a conversation I was going to have with them!

The only thing that was different with this user was that in troubleshooting this issue we had set the user up to receive the journalling non delivery reports. I figured that if the emails were not being delivered, maybe sending him the errors would help. However no reports were being received either.  However, according to KB 2829319 this behaviour can be seen. Although I had removed the journal receipient in the web gui, the emails were still not being journalled until I added another external email address to the configuration using the powershell command set-transportconfig -JournalingReportNdrTo [email protected]

At this point, all the email started to be journalled.

Note that we only added the recipient into the mix when I was trying to work on the initial problem so it looks like this wasn’t the only fix.

The other thing we did was change the outboundconnector to be onpremises. Changing the setting in the GUI we then ran Set-OutboundConnector archivemymailconnector -routeAllmessagesviaonpremises $true.

These two combinations seemed to fix the issue.

One thing I also learnt was that it is really useful to send multiple emails between changes and keep the subject line starting the same. Use the date/time at the end of the email. That way you can sort the email logs by Subject and just pick out the ones you were working on. By having the subject start with zzz followed by Round X (ie zzz Round 1 – change connector – 1345pm and zzz Round 1 – change connector 1346pm ) then the results are likely to appear at the end of your mail logs if you sort by subject.  Sorting by Date was not always a good idea as mail flow could occur between mail coming into the server and mail leaving the server.