Eudora to Mac OS X Mail.app Import

I’ve finally made the move over from Eudora to Mac OS X’s built-in Mail application.

I put it off for a couple of years, but in the end I was getting more and more fed up with Eudora’s “clunkiness” and general operational slowness compared to the rest of the OS (I presume due to it being a legacy Carbon application, as opposed to it being written in Cocoa specifically for OS X). Oh, and Mail looks prettier too!

What finally inspired me to take action was discovering Eudora Mailbox Cleaner, a great little freeware application from Andreas Amann to help import mailboxes and filter rules from Eudora to Mail.app.

The Mail application can do this itself, but gives less than satisfactory results because, as Andreas says:

Eudora mailboxes do not adhere to a standard format which makes importing into other applications somewhat of a pain - the default import function for Eudora mailboxes of most mail client thus exhibit some problems, namely:

Most HTML and rich-text messages are not imported properly (you see all formatting tags instead of the properly formatted message)

All messages are imported as “unread,” i.e., the original message status flags are ignored

Attachments in the messages are lost

Sent messages might lose their original date and show the date of import instead

There is no straightforward way for importing Eudora’s nicknames into the MacOS X Address Book

There is no option for importing Eudora’s filters

I’d be lying though if I said everything went smoothly. I rebuilt my Eudora mailboxes as advised before starting, but Eudora Mailbox Cleaner stopped responding half way through the import, and after leaving it for a few minutes to see if it found its feet, I finally had to cancel the operation.

Unfortunately that meant I didn’t know what had been imported and what hadn’t. I should stress that I suspect the shear amount of mail (including some damaged) was most likely the cause, not Eudora Mailbox Cleaner (although a log would have helped).

I doubt the average user would experience the same problems, but it’s worth noting just in case.

I probably have over a hundred mailboxes and thousands of messages going back some seven years to when I first started using Eudora. I think the largest single mailbox has over 9,000 messages in it (I need to do some serious cleaning!).

In the end I decided the best course of action would be to delete the entire “Import” folder in Mail along with all the mailboxes that had been successfully imported before the process stalled, and start over. This time though I’d split the job into several chunks, by separately importing each of top level folders in my old mailbox hierarchy.

I deleted the Import folder, clicked to confirm I wanted to remove it along with all its mailboxes, and then emptied Mail’s trash. I then quit Mail again, and set about re-importing my mailboxes

Everything went fine (as I thought) and on importing the last of the mailboxes, I finished by importing my Eudora filters (a major reason for resisting moving, because currently Mail can’t import these at all).

I ran the scripts included by Andreas to rebuild imported mailboxes and activate the imported filters.

But when I went back into Mail, the Import folder I had deleted before was back again along with all the new Import-n folders!

I deleted it, quit, re-launched, and it was gone. Only to come back after I quit and re-launched again!

I went into the mail folder in ~/Library/Mail, renamed the Envelope Index file as “xEnvelope Index” and launched Mail again, forcing the rebuilding of the original file.

That appeared to work. The old import folder didn’t appear again after that.

Relieved, I then went to check my imported filters. Everything seemed fine, except that all the filter rules to move mail to other mailboxes (99% of them) were missing the destination mailbox.

“Oh well …” I thought, “This is still better than having to do the rules over from scratch.” And I proceeded to step through the long list (I have around 160 filters I think), editing each filter.

After doing about 50 or so, I started coming across quite a few filters that were no longer relevant. Scrolling down to the bottom, I saw the ones there were important, so I started working up from the bottom.

That would have been fine except for one thing.

Unknown to me, I had 2 sets of my filters in there. They had actually been imported twice. Initially with the failed Eudora mail folder import, and then again alone.

Being a job that had stretched on until long after I had intended to be fast asleep in bed, it took several, “Didn’t I just map a filter to this folder?” thoughts before I finally realised something really wasn’t right, and discovered the duplication!

So, I go through and delete all the duplicate filters that I’ve not yet edited. That would have been simple enough, except that I had now done some at the top and some at the bottom (ok, and a few in the middle!) and they all look much the same in that long list …

Anyway, I’m just about finished, and having totally deleted a couple of rules by mistake, it suddenly occurs to me that I could have just deleted the filters file and re-imported the whole lot. Duh!

I quit Mail, located the MessageRules.plist in ~/Library/Mail, renamed the filter file and its backup by prefixing them with an x (incidentally, this is what I always do — much easier than unnecessarily copying backups to the desktop). Then I ran Eudora Mailbox Cleaner again, but just to import the filters.

Open mail. Great! The filters are there, AND pointing to the right mailboxes. At last!

Maybe not …

Afer quitting and re-launching Mail, I find the filter rules are again showing no destination mailboxes as being set!

I’ve had enough. It’s time to get my hands dirty.

I open the MessageRules.plist text file and discover that the file paths to all the mail folders are prefixed with “Import/” I suspect this is the problem, so I do a quick search and replace to delete every occurrence and re-save the file.

With baited breath I launch Mail. Thank God! Everything is sweet, and I can collapse into bed….

There are a couple of things I miss from Eudora though. Namely the filter report that tells me what mailboxes have had new mail filtered into them after a mail-check, and the ability to label messages (e.g. I used to be able to locate all emails with download links by searching for the label “download links”).