Hi douggoss,

I’m no expert on importing Outlook messages to Gmail — in the past, I’ve only used the IMAP method.

I did a bit of digging and I found decent tutorials on both the IMAP method and an alternative, using a port to Thunderbird and from Thunderbird to GML and from there to Gmail. I’m not sure if either will work for you, but the links are below. Let me know how it works out!

GML – http://www.wikihow.com/Import-Archived-Outlook-Email-Into-GMail-Using-GML

IMAP – http://www.labnol.org/internet/email/export-outlook-email-to-gmail-pst-backup/1938/