How to Copy All Email From MS Outlook to Gmail

I have been hosting my own Microsoft Exchange Server from my home for the past five years. Recently the hard drive went south on the only Domain Controller I had in my network. As luck would have it this occurred on the day before a two week family vacation. After several failures attempting to restore Active Directory I quickly decided to host our email on Gmail. I pointed DynDNS to Gmail's servers and voila! After returning from vacation I got around to bringing the Exchange Server back up. For now I decided I would stick with Gmail (yes I drank the Kool-Aid).

So Google has a neat tool  Google Email Uploader that does the trick (Contacts & Email). The only thing now is my calendar (I have lot's of birthdays, anniversaries, and other recurring appointments)...

One major downside for me with the whole process was having to go through and fix many of the tags. Google doesn't use folders; instead the concept of a "tag" is used. The app converts each folder to a tag but if you have folders inside folders, the entire folder path becomes the tag. For example: "Employment\Benefits\401K\" was one tag. I flattened this structure by creating three tags, "Employment", "Benefits", and "401K", and then assigned all three tags to the emails in the folder. The process led me to simpliify my filing structure as well.