I have tried the Google migration tool, Thunderbird import, translation to MBOX, and a few other semi-automated tools but encountered the "unknown sender" issue. The strongest solution seems to be with an Exchange server in what is essentially a two-step process.
- Copy emails from PST to Exchange mailbox (will mirror in IMAP4 mailbox)
- Copy emails from IMAP4 mailbox to Gmail mailbox
I was able to follow those guidelines using the pre-configured VHD of Exchange Server 2007 SP1 (evaluation version) and Virtual PC 2007 (free).
MS Virtual PC 2007 SP1
http://www.microsoft.com/en-us/download/details.aspx?id=24439
MS Exchange Server 2007 SP1 VHD
http://www.microsoft.com/en-us/download/details.aspx?id=14901
Besides using Microsoft Outlook 2007 to move emails from PST to an Exchange mailbox (will mirror in IMAP4 mailbox), I also found it helpful to use Thunderbird to move emails from the IMAP4 mailbox to Gmail. It worked fine when I tested with Outlook but I prefer the Thunderbird interface and it also helped keep things straight.
Below is the short-hand detail, with many thanks to the posts and references that others provided along the way:
Host PC Desktop -> Start -> Control Panel -> Network Connections -> Properties -> Install -> Virtual Machine Network Services
Virtual PC -> Edit -> Settings -> Networking Settings -> Adapter 1 -> Select the desktop network connection that you just updated
Virtual PC -> Edit -> Settings -> Shared Folders -> to copy any data or installation files on your host desktop
Virtual PC Desktop -> Start -> Control Panel -> Network Connections -> Properties -> TCP/IP -> Obtain IP + Obtain DNS
Exchange Management Console -> Organization Configuration -> Hub Transport -> New Accepted Domain
Exchange Management Console -> Organization Configuration -> Hub Transport -> E-mail Address Policies -> Edit -> Add -> Select accepted domain + Set as Reply
Exchange Management Console -> Organization Configuration -> Hub Transport -> Accepted Domains -> + Set as default
http://exchangeserverpro.com/change-business-email-domain
Exchange Management Console -> Server Configuration > Client Access > POP3 and IMAP4 -> Authentication -> Plain text logon (optional if you are running into issues logging in later)
http://exclusivelyexchange.com/how-to-connect-pop-and-imap-clients-to-exchange/
Administrative Tools -> Domain Controller Security Policy -> Account Policies -> Password Policy -> Set preferred requirements (Ex. Disable complexity)
Administrative Tools -> Domain Security Policy -> Account Policies -> Password Policy -> Set preferred requirements (Ex. Disable complexity)
Administrative Tools -> Services -> Microsoft Exchange IMAP4 -> Start + Automatic
Exchange Management Console -> Recipient Configuration -> Mailbox -> New Mailbox -> User Mailbox -> Create mailbox for new user + Select mailbox database
http://technet.microsoft.com/en-us/library/ff406204%28v=exchg.80%29.aspx
Exchange Management Console -> Organization Configuration -> Add Exchange Administrator -> Select user + Exchange Organization Administrator role
http://technet.microsoft.com/en-us/library/aa998008%28v=exchg.80%29.aspx
Install Outlook on virtual hard drive (not recommended in general but works for transfer to Gmail)
Copy PST file to virtual hard drive
Add Exchange account (uncheck cached Exchange mode)
Add PST file
Add IMAP4 account to connect to your Exchange mailbox through IMAP (see account details below)
Add Gmail account
[email protected]
LITWAREINC/user
IMAP: EX07SP1.LITWAREINC.COM:993 (SSL)
SMTP: EX07SP1.LITWAREINC.COM:587 (STARTTLS)
Test Account Settings -> Should log onto incoming mail server but may not successfully send test e-mail message (not necessary for transfer)
Copy from PST to Exchange mailbox (will mirror in IMAP4 mailbox)
Copy from IMAP4 mailbox to Gmail mailbox (I tested this successfully with Outlook but used Thunderbird for the mass transfer)
Note: My trial version expired (incorrectly) and would sometimes restart. Occassionally, I had to restart Microsoft Exchange services.
Administrative Tools -> Services -> Microsoft Exchange Active Directory Topology Service -> Restart
Administrative Tools -> Services -> Microsoft Exchange Information Store -> Restart