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Microsoft Exchange 2003 to Office 365 Migration

September 28, 2013 Leave a comment

System Notes: Microsoft Exchange Server 2003 Enterprise, Microsoft Office 365 E1

I have just recently completed a migration from a legacy on-premises Exchange 2003 e-mail server (running Exchange 2003 Enterprise; only one server/one mail database; 85 user mailboxes) to Microsoft Office 365 (cloud-based e-mail solution; using plan E1). Here are some of my personal observations and recommendations for this process:

  • I consulted with 3 different “migration” companies, but ultimately ended up doing this process myself with no outside help. The cheapest of the 3 companies was over $4K for assistance with the 85 mailboxes we had to migrate. The worst part of the migration process was converting each of the on-site Outlook 2010 clients to connect to Office 365, as it ended up taking the most time and being the most disruptive to the users. None of the companies offered to have someone on-site to help with this process, or wanted even more money specifically for that. Save yourself some grief and hire a temporary contractor for this portion of the project, as the rest of the actual migration is not hard at all, assuming you have a good plan in place.
  • We used the Exchange RPC interface to do a “cutover” migration from the Exchange 2003 server. Two notes on this process:

1. I was able to stop, restart, delete, and recreate the batch migration I set up as needed, with no duplication of users or any data in the user mailboxes. I was very worried about this initially, and could find no hard data on it online, so I decided I would just delete the mailboxes and re-migrate if duplication became a problem (which it did not).

2. Existing mailboxes that had the same username as those that were being migrated were blocked from migration and had to be completely deleted before they could be imported successfully. We have multiple domains set up on Office 365, and I had 5 test accounts set up with a domain that was different from the one I was migrating from Exchange 2003. However, the usernames were the same, and this is where I discovered the issue.

  • Do not just shut down your Exchange server once the migration is complete and you are running fully on Office 365. Even the older Exchange 2003 integrates extensively with Active Directory, and it must be uninstalled correctly or you are bound to have problems with Active Directory in the future. This is what I did:

1. Removed all mailboxes from the Exchange 2003 server.

2. Added a correct primary e-mail address that corresponded with the Office 365 e-mail address under the primary SMTP address field in Active Directory for each user. This is necessary for several Active Directory to Office 365 automation routines that we use, and may be required as well if you are using any of the directory synchronization routines that Microsoft provides.

3. Before uninstalling Exchange itself, I removed all supporting programs, including our Backup Exec Exchange agent, the Exchange User Monitor, and the Exchange Auto-Accept Agent.

4. If you get an error message when trying to uninstall Exchange 2003 from Add/Remove Programs, check out this link for a possible solution. We had one user account that the mailbox had been successfully removed from, but that still had the Exchange attributes attached in Active Directory. I was able to remove these via the Exchange user wizard. I did not have to remove the SystemMailbox from our Exchange environment, but I have seen others indicate they had to do this in their environments.

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Controlling local SMTP mail relaying with Exchange 2003

September 17, 2008 Leave a comment

The organization needed to enable a specific database server to send out e-mail confirmations to remote users after specific events have occurred. Simple, I thought, as I had previously configured just these options back when we first installed our Exchange 2003 Standard server over a year ago. I was wrong though, as the confirmations were not being sent, seeming to just disappear out into the void.

  1. First step was to run some simple tests using Bmail (which is a free command-line SMTP mailer, available here. Initial tests were run from my local workstation, and lucky for me, led me to the solution right off the bat.
  2. The Bmail tests from my workstation immediately produced SMTP 550 5.7.1 “Unable to relay” error messages. What? My workstation should be authorized to use SMTP…
  3. I then ran the exact same test from the server in question with the problem. Same result as my local workstation, SMTP 550 5.7.1 errors.
  4. Time for a Google search on the issue. This lead me to the Default SMTP Virtual Server Properties dialog box (Exchange System Manager -> Organization -> Administrative Groups -> First Administrative Group -> Servers -> Server01 -> Protocols -> SMTP -> Default SMTP Virtual Server). From the dialog box, I went to Access, then the Relay restrictions Relay button.
  5. As I previously indicated, I had not changed these options since I first set up our Exchange 2003 server. The list of server IP addresses under “Only the list below” was incorrect, and it contained IPs that were no longer in use, and was missing the address of the server with the mail relaying problem. It was simple to correct the list.

Additional Notes:
You have all kinds of options with the Relay Restrictions window. I strongly suggest sticking with the principle of least access, and only granting open relay access to those systems which really need it. Adding a domain name or a group of IPs to the list seems a very bad idea to me, since as indicated, this is not an area that is visited often. Also, assuming you are using Outlook clients with your Exchange 2003 server, make sure you leave the “Allow all computers which successfully authenticate to relay, regardless of the list above” option checked, or your Outlook clients will not be able to send outbound SMTP (Internet) mail. My local workstation system was unable to relay with Bmail because its IP address was not on the list, and I was attempting to send mail directly from the command line, outside of an authenticated Outlook session.

Categories: Exchange 2003, mail relay, SMTP