I needed a way to have access to my work messages without getting stuck on any single platform or computer. A quick check in the internet revealed three ways to move the message from Outlook to Gmail.

The first one was extremely complicated and it requires shifting from Outlook to Outlook Express, then to Thunderbird and then using some software which will then forward the messages into your Gmail account. It required too many steps to do it, and you might get labeled as spam since you would be akin to mass emailing your old message. If like me, a short few months could easily meant a thousand email messages. In addition, you will lose the date stamp on each mail messages which sort of defeat the purpose of using Gmail for archiving your old mail.

The next method I found was provided by Google themselves, it was called a Google Email Uploader.

The Google Email Uploader, as explained by Google, is a desktop utility for Microsoft Windows that uploads email and contacts from other desktop email programs (like Microsoft Outlook) into your Google Apps mailbox. The Email Uploader has the feature to preserve information such as sent dates and sender/recipient data, as well as the folder structure used by the other email program. Looks good, so I went to their download page and tried it out.

http://code.google.com/p/google-email-uploader/

Unfortunately, after installing and trying it, I got an error message. Tried it a few more times, but to no avail, it did not work. In the end I did not bother to troubleshoot the problem because there was another easier and better way of uploading the mail messages.

If your email could support IMAP, all you got to do was set up the IMAP account in your email program and just simply move or copy over your messages to that account. The Outlook program has IMAP, and so does Outlook Express or in its latest incarnation, the Windows Mail, has this feature. I suppose any email program that supports IMAP would work.

After setting up your IMAP account and having it connect to Gmail, you can now proceed to copy or move your messages to the respective folder in Outlook or Windows Mail, eg Inbox to Inbox, Sent Items to Sent Mail, even your Drafts to Gmail Drafts folder.

Be warned, if your PC is slow and near obsolescence, and you have a lot of messages to transfer (say about 1000, which was what I had accumulated for the past 3 months of year 2008), you will need a lot of patience to move it over. Took me about 12 hours+ to move it over. I have to move the files a bunch of them at a time, moving about 10-20 messages for each transfer. Otherwise my Outlook will hang, sometimes taking along my desktop PC along with it. It was terribly slow, and decided there was no need to backtrack and upload the previous years messages.

Using IMAP with Gmail, any labels that you’ve created will show up as a subfolder in Outlook or Windows Mail. Handy for searching your messages. Plus you never need to delete any files with its big storage capacity.

However, the biggest advantage could also be the biggest drawback when using IMAP was that all your messages will be synchronized. Wouldn’t you think that was good? If your messages weren’t so many, yes. I tried it with my personal Gmail account which has about 8000+ messages, it took a long while to sync with Windows Mail in my house. Fortunately I was running on a new PC that could handle the data load. In my office, my old PC screamed and cried foul, and Office Outlook died barely touching a few hundred messages. Finally I gave up on the idea of using IMAP with my personal Gmail account. Perhaps I should clean out my Gmail account and delete the accumulated chain mails, spam and promotional messages. Well, maybe one day when I have nothing to do…