There is no easy solution to this problem currently, but there is a solution: build your own Exchange server.
If you’ve found your way here, you probably understand the problem: when trying to import an Outlook .PST file into gmail, instead of the original sender, “unknown sender” shows up in its place. There are a few kludge solutions to this problem. One article I read suggested building a Windows Server infrastructure complete with your own Exchange server as a work around. Thanks to fast SSD’s, my patience was up to the task, but hopefully yours will not be quite as tested as mine was.
We’ll build two VM’s: one running Windows 7 with Outlook 2010, and a second running Windows Server 2008 R2 SP1, which will serve as a DC and the Exchange box.
Exchange has changed a bit since I last used it professionally, and it is not plug and play. Here are some tips to get you up and running quicker than I was.
Building the Exchange Server/DC
1. If you’re using a cloned install, run SYSPREP before cloning. Usually, you can get away with cloned machines and duplicate SID’s. No so with Exchange. If you don’t, here’s what you can expect when you try to launch the Exchange management console. Not fun.
Unexpected error [0x145AAC30] executing command ‘Get-LinkedRoleGroupForLogonUser’
2. Use the Enterprise edition of Windows Server 2008 R2 SP1. The Standard edition won’t work.
3. Stick with Windows Server 2008 R2 SP1 for now. I tried the Windows 2012 RC released a couple of days ago, and it was flaky on VirtualBox.
4. The easiest way to go is to just install Exchange and DC functionality on the same box. There were problems getting the Exchange Management Console to start when I tried separate server installs. This is a single-purpose install, not a production infrastructure.
5. After you make your server a domain controller, perform Windows Update through to completion.
Shortcut: Paste this into PowerShell (for a Typical Exchange install — others have different requirements):
Add-WindowsFeature NET-Framework,RSAT-ADDS,Web-Server,Web-Basic-Auth,Web-Windows-Auth,Web-Metabase,Web-Net-Ext,Web-Lgcy-Mgmt-Console,WAS-Process-Model,RSAT-Web-Server,Web-ISAPI-Ext,Web-Digest-Auth,Web-Dyn-Compression,NET-HTTP-Activation,Web-Asp-Net,Web-Client-Auth,Web-Dir-Browsing,Web-Http-Errors,Web-Http-Logging,Web-Http-Redirect,Web-Http-Tracing,Web-ISAPI-Filter,Web-Request-Monitor,Web-Static-Content,Web-WMI,RPC-Over-HTTP-Proxy -Restart
7. Now, install Exchange 2010 SP2 with a Typical install. If you do receive any error messages, read them carefully and don’t give up.
8. Once Exchange is installed and you’ve rebooted, create a new user, and create a new mailbox for that user.
9. Verify IMAP4 is enabled for the user in user Properties.
10. Enable Basic authentication for IMAP4, then restart the Microsoft Exchange Server IMAP4 service using services.msc.
Congratulations. You’ve configured the exchange server on your DC. Now… on to the Outlook box.
The basic idea is to use Outlook to attach to your Exchange server and copy all of your desired .PST email archives to your new mailbox. Then, delete Outlook’s default Exchange connection in Control Panel and replace it with an IMAP connection to the Exchange server instead. Add another IMAP connection to gmail.
Once that’s done, you can use Outlook to move the mail from your Exchange mailbox to gmail, and the “unknown sender” problem will be gone. Here’s how I did it:
1. Add the FQDN of the domain controller to the local HOSTS file on the Outlook box.
2. Through Control Panel, add an Exchange connection for the account you created on the DC/Exchange box.
3. Make an IMAP connection for your gmail account. Use SSL for the IMAP connection and Auto for SMTP. Here are the current gmail required settings according to Google:
|Incoming Mail (IMAP) Server – requires SSL:||imap.gmail.com
Use SSL: Yes
|Outgoing Mail (SMTP) Server – requires TLS:||smtp.gmail.com (use authentication)
Use Authentication: Yes
Use STARTTLS: Yes (some clients call this SSL)
Port: 465 or 587
|Account Name:||your full email address (including @gmail.com) Google Apps users, please enter username@your_domain.com|
|Email Address:||your full Gmail email address (firstname.lastname@example.org) Google Apps users, please enter username@your_domain.com|
|Password:||your Gmail password|
4. Once you have both accounts configured, you’re in business. Copy your mail from the .PST to the Exchange mailbox in Outlook.
5. Then, exit Outlook and remove the Exchange account connection in Control Panel.
7. Launch Outlook, and copy your mail from your exchange mailbox to the gmail folder of your choice.
8. Verify your gmail folder, and congratulate yourself for an heroic solution to a simple problem that would make Rube Goldberg proud.
Fun? It was kind of a PITA for me — but maybe if I had this guide to start with, it would have been ALMOST fun. Let me know if you get it to work.