Mails stuck in queue when Automatic Replies are enabled

Question

We have a new Exchange 2013 server and moved a few pilot users from the 2010 environment to it.
Everything seems to work OK but we just encountered a strange issue. One of the users turned on his automatic out of office replies and when people send E-mail to his mailbox they receive a 'Delivery delayed' e-mail. All mails to this account seem to be
stuck in the queue (shown in the Exchange Toolbox – Queue viewer) but they DO actually arrive in his Outlook.
The error message in the queue for his messages is: Recipients:  [email protected];3;3;[{LRT=};{LED=432 4.2.0 STOREDRV.Deliver; Agent transient failure during message resubmission[Agent: Mailbox Rules Agent]};{FQDN=};
 After turning off his out of office replies, the queue emptied instantly, and no duplicate mails arrived in his mailbox. After turning it back on the queue started filling up again with new mails.
Other pilot users have the same issue.
Has anybody seen this issue before? I checked space on the drives and there seems to be no issue there (so no back pressure issue).
thanks!

Answer 1

We opened a case with Microsoft support. It took a few weeks for them to find what was causing this issue. I will just copy/paste the summary they gave us.
Reason:
So the error was thrown by the Transport Service when we are trying to submit the mail.
We also compared the difference between earlier version and CU5 and found “XORIGFROM=[email protected]” is the difference, we started using XORIGFROM verb from CU5.
We did further analysis and found During SMTP Session, we check if the XOrigFrom argument is allowed according to EHLO, capabilities and permissions. 
While checking this permission, we check if the session has permission to accept organization headers, and this is where we are failing. 
# we checked the effective permission for "Mailservername" on Default receive connector and found that we had "deny" permission on: Accept Organization headers
# We also found that the security group "Exchangelegacyinterop" had deny permission for "accept organization headers" on the default receive connector 
# We found that the Exchange server "Mailservername" was a member of "Exchangelegacyinterop"
# So we removed the "Exchangelegacyinterop" and added the "Mailservername"
# we gave "Allow" permission on "Accept organization headers"
# we restarted the MSExchange Transport service
# We sent an test email to the OOF enable mailbox 
# we found that we got the OOF reply and also the email did not stuck in the queue
# Issue resolved