How to sanely migrate email messages from Apple's Mail.app to Google Apps' GMail

January 18, 2009 5:34 PM

How do I move around 2000 messages from Apple's Mail.app (10.4) to a Google Apps (Premier) GMail account quickly and efficiently?

Maintaining the received dates and any miscellaneous attachments is a must.

I'm helping a company move their 35 employees with traditional POP download-it-to-your-hard-drive-then-delete-it-from-the-server accounts to Google Apps-based GMail accounts. They opted for the Premier ($) version of Google Apps.

I know about enabling the GMail account's IMAP service, then adding the IMAP account to Mail.app, and then dragging in your messages. When I tried that, it took hours upon hours to move very few messages, often timed-out for no good reason, and even with the activity window open, didn't give very detailed feedback about the progress of the operation. The company has a "business-class" DSL line. Speedtest.net reports that they're getting 300 kbps upstream from their office to San Francisco. (I assume Google's servers are somewhere in San Francisco.)


I'm willing to convert the mailboxes to some other format (mbox, etc.) and use a PC tool. Google themselves provide a tool to suck in messages from an existing IMAP server (which doesn't help directly), or Google Email Uploader, which only seems to work with Outlook, Outlook Express, or Thunderbird. I've also heard about IMAPSync, but I'm not certain it will do what I want.

I do have a PC available, if needed. For the Mac, I do have Emailchemy available.

posted by Wild_Eep to computers & internet (8 answers total)

Can't you used Emailchemy to convert Mail.app to Thunderbird, and then use the Email Uploader? It sounds like you have all the tools you need.
posted by Blazecock Pileon at 6:17 PM on January 18, 2009

Gmail Loader? "The application works by reading your existing mail files, and forwarding them to GMail. It does not delete the mail from your local computer. Email can be set to arrive at GMail in either your 'Inbox' or 'Sent Mail'."
posted by _Mona_ at 6:31 PM on January 18, 2009

Google Apps Premier is supposed to come with email migration tools.
posted by Good Brain at 7:48 PM on January 18, 2009

GMail Loader doesn't preserve the dates properly.
posted by Wild_Eep at 9:20 PM on January 18, 2009

I've only ever done this with a free Gmail account. I used the copy-to-IMAP folder method, and it worked flawlessly.

You might be looking at some Apps For Your Domain bizarreness here. Perhaps you might try setting up a dummy free Gmail account and seeing whether IMAP upload works any better to that; if it does, you should then be able to use Gmail's own IMAP slurper to copy everything to your live account before emptying and deleting the dummy one.
posted by flabdablet at 9:22 PM on January 18, 2009

I'll be honest, all the email conversion tools do a consistently poor job with metadata other than sender and recipient (dates, flags, other header information). Your most reliable and consistent bet is to figure out what the bottleneck is with IMAP transfer and fix that.
posted by Blazecock Pileon at 9:29 PM on January 18, 2009

Far and away, the best option I've found is Emailchemy. Not free, but in my testing, it has been fantastic. Windows, Mac OS X, and Linux versions. Very responsive developers. Highly recommended for us Mac folk who have boat-loads of POPed mail to upload to Google.
posted by Wild_Eep at 1:42 PM on January 27, 2009 [1 favorite]

I should note that when I wrote the question, I was unaware that Emailchemy had added a dedicated GMail upload component. I was only aware that it would take Mail.app mailboxes and turn them into true mbox files.
posted by Wild_Eep at 1:51 PM on January 27, 2009 [1 favorite]