I decided to write a series of blog posts about moving the tens of thousands of emails from years of life online in my local email into Google's cloud. This is Part 2. Read Part 1.

In the last blog post, I was just getting started and formulating a strategy to migrate tens of thousands of old email messages from Apple Mail into Gmail. I'm far from finished, but I did get off to a good start so I wanted to post an update.

As I wrote, the main challenge, aside from the sheer volume of emails, is maintaining the meta-data of each message from years of using MailTags. What I've found out is that there is no automated way to make this happen, so I've been formulating my own solution. This is the approach I'm taking:

1. Activated IMAP for my Gmail account; created the corresponding IMAP account in my Apple Mail app.
2. Synched up. This took the better part of two days for around 30,000 messages, which got me about 75% there before labeling.
3. Created labels in Gmail that match my Smart Mailboxes in Apple Mail. Note that my Smart Mailboxes are all managed with MailTags meta-data, so this is the solution to not being able to migrate the old messages in an automated fashion.
4. Drag the messages in each Smart Mailbox to their matching label in the IMAP account in Apple Mail. Wash, rinse, repeat. This will upload and label the messages. The pitfall here is that I'm bound to duplicate some emails that are already in Gmail.

So that's where I'm at. I have about 12,000 messages to go in around 50 Smart Mailboxes. This represents just about all of the old emails I've been managing for years and years. Once that manual work is done, it's time to check for orphans in Apple Mail -- emails that I want to take with me, but that I may have miscategorized or failed to categorize at all.

Then I need to figure out a Gmail search that will allow me to identify and delete duplicates, if this is even possible. Finally, with all my messages stored in the cloud, I have to clean up my Gmail inbox, currently around 13,000 emails, which to this point has basically been a dumping ground for all incoming messages since I signed up to use Google Apps for my personal email in June 2007.

Yep, it's a process. More to come...