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This is such an odd issue it's difficult to describe, so please bear with me.

I have a client ([email protected]) who has purchased Hosted Exchange services from Rackspace. He has no problems sending email to anyone except ONE person ([email protected]).

The facts:

Why would email addressed to the alias go through no-problem, but email addressed to the primary account ([email protected]) seemingly vanish into the ether?

BastianW
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user177410
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  • Check your junk mail folder? – Michael Hampton Jan 10 '15 at 18:22
  • How is the "alias" set up? There are lots of ways to do that in exchange (add additional email address to existing mailbox, create a DL, create a mailbox with a forwarding rule, etc.). The method used is diagnostically relevant. – briantist Jan 10 '15 at 19:40
  • MS' mail services are known for hiding mails from it's recipients. – sebix Jan 10 '15 at 20:46
  • Michael... yes, that was done. Also checked other folders in case a rule or filter was diverting it to a different folder. – user177410 Jan 10 '15 at 21:43
  • Brianlist... I asked the administrator of the receiving account how the alias was set up. His response... "The alias is set up as a traditional alias". I don't think there's anything special going on here in terms of alias creation. – user177410 Jan 10 '15 at 21:47

2 Answers2

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You didn't give a lot of information about tools you're using to troubleshoot this, so I'll describe the approach I take when I encounter a problem like this. Hopefully this will help you find the solution:

Since you've established that email can be delivered between the two Exchange orgs in general, I would run a message trace in O365 against the recipient's primary address (not the alias). This will tell you what, if any, transport rules were hit on the way through. Most importantly, it will tell you the final delivery status.

If the delivery status is anything other than delivered, I would look at any transport rules hit and the final status to identify what was done with the email (dropped, quarantined, redirected, etc.). If that doesn't get to the bottom of the issue, I would (reluctantly) create a service request with MSOL support.

If the message has a status of Delivered, I would be looking at mailbox related things. I always use OWA for this because I can verify that the mail exists in the mailbox before checking any clients that could potentially have communication or offline copy issues. I would be looking at inbox rules, junk mail, "Clutter" (the new feature), deleted items, recoverable deleted items.

john
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  • Very helpful. I'll forward this along to the person who's administrating the O365 account and will report back with results. Thanks! – user177410 Jan 11 '15 at 17:11
  • John, See my note below for the solution. I did reach out to the person administering the O365 account. He ran it through the paces with Microsoft and they could find no problems on their end. So then I turned to Rackspace's administers. It took a bit of doing but they finally produced a log of sent email confirmations. Within that log was the hint that led to the eventual "ah ha!" moment. Thanks. – user177410 Feb 16 '15 at 21:39
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I'm reporting back here in case anyone else encounters this.

It turned out that [email protected] actually had used Rackspace (via a reseller) before he switched email services over to Microsoft's Hosted Exchange. The Rackspace reseller with whom Mike was dealing apparently never completely deleted Mike's account from their Control Panel. So when my client (Kirby) tried to send email to Mike, the message never made it out of Rackspace's datacenter. As far as Rackspace was concerned, they were delivering the message correctly to an email account that still existed on their servers.

The Rackspace technician "hinted" that perhaps I should contact Mike's prior Rackspace reseller to have them fully remove Mike's account from their reseller Control Panel (Rackspace was kind enough to suggest the name of the reseller). After the reseller fully removed Mike's account from their reseller account the original problem went away.

And they lived happily ever after.
The End

user177410
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