We are in the migration process from 2010 to 2013. We have installed 2013 and have tested moving mailboxes and all is well except for our transport rules.
We have several rules where groups of users have any outgoing email with attachments have to have them approved by managers due to HIPAA compliance.
After the initial install of 2013 we immediately had issues where managers had to approve the emails two or more times before they would go out. We read where transport rules didn't translate well in the upgrade so we deleted the rules on the old server and recreated them on the new to no change. Currently most senders have to have their email approved twice. My email, since I'm the one guinnea pig that moved my mailbox to the new server, won't go out at all, it is stuck in a loop where it keeps going to my manager seemingly forever.
I'm hesitating to migrate actual user mailboxes till this is settled, but this might also go away when we retire the 2010 server so I'm torn.
I find little written about transport rule troubleshooting, but I did run a delivery report on an email I sent and found the message sent to an approver, approved, sent to an approver, approved, sent, etc. I'll paste it below my signature.
Any assistance or insight is appreciated.
Jim
Delivery Report for David.Simpson@wiXXXXXX.com
Submitted
3/26/2014 11:27 AM OPT-EXCH1
The message was submitted to opt-exch1.local.xxx.com.
Pending
3/26/2014 11:27 AM opt-exch1.local.xxx.com
Message was received by opt-exch1.local.giftrapcorp.com from opt-Exch1.local.xxx.com.
Failed
3/26/2014 11:27 AM opt-exch1.local.xxx.com
The message was rejected by a rule set at the organization level. For more information, check your organization's Transport rules.
Pending
3/26/2014 11:27 AM opt-exch1.local.xxx.com
The message was sent to a moderator. Messages sent to this address must be approved by a moderator before delivery.
3/26/2014 11:32 AM mail01.local.xxx.com
The message was approved by the moderator.
3/26/2014 11:32 AM mail01.local.xxx.com
The message was sent to a moderator. Messages sent to this address must be approved by a moderator before delivery.
3/26/2014 11:32 AM mail01.local.xxx.com
The message was approved by the moderator.
3/26/2014 11:32 AM mail01.local.xxx.com
The message was sent to a moderator. Messages sent to this address must be approved by a moderator before delivery.
3/26/2014 11:33 AM mail01.local.xxx.com
The message was approved by the moderator.
3/26/2014 11:33 AM mail01.local.xxx.com
The message was sent to a moderator. Messages sent to this address must be approved by a moderator before delivery.
Failed
3/26/2014 11:34 AM mail01.local.xxx.com
The moderator has rejected this message.
Jim Tall