Okay, now I’ve stopped giggling madly and rolling around on the floor in an equally insane manner, I’ll start again.

Exporting email, addresses and calendars from Outlook to a Mac is NOT a trivial exercise. It’s a pain in the arse.

And it’s a major failing for Apple. I read an article recently in The Age that said this and — I freely admit — that I thought “It can’t be so. Surely it can’t be that hard?”.

By the way, just on a related tangent, if mail crashes after an import,  go to <user>\Library\Mail\Mailboxes and delete the import folders. That’ll bring it back.

The issue is that the import folders can’t handle really huge import folders from Outlook. You’ve got to be a bit more reasonable about the size. For example, my friend had nearly 2,000 messages in their inbox. Mail (and Entourage for that matter) can’t handle the import or the firing-up of this size of folder. Spread the messages out a bit and you’re fine.

But back to my job for the weekend: moving email, contacts and calendar from Outlook to Mac. Easy?

Hah.

For the punters out there, here’s how I achieved this astonishingly difficult goal…in hindsight, I should have clicked the links in the above-mentioned article and bought a copy of 02M.

Now from the look of it, this whole thing could also have been done with a handy app called SyncWiz. Only I didn’t have the cash (am a bit broke at the moment, which is — ironically enough — the reason I’m doing this job).

Migrating the Mail

Part One: Get the mail into Mozilla Thunderbird.

Why? Because it has a “mbox” standard file structure. Outlook has a native system which nothing else on the planet can read, including — oddly enough — Entourage for Mac. You’d think by being the same company they’d talk to each other.

Perhaps not.

1. Download Mozilla Thunderbird and install.

2. Import Outlook mail to Thunderbird.

3. Tidy the folders so there are no more than 400 messages per folder. In my case, I was importing from a friend’s email account which in some cases had almost 2,000 messages in the inbox. A great big issue.

4. Copy the Thunderbird mail folders, found in the following path to your mac. I used an external drive because I couldn’t be arsed trying to network the two computers; I have only a certain amount of patience and time on the planet after all. Oh, here’s the path:

c:\Documents and Settings\YOUR USER\Application Data\Thunderbird\Profiles\<incomprehensible weirdness>.default\mail\Local Folders\

Nothing like having a clear, easy to find and understand folder path, eh?

Part Two: Get the files over onto the mac

Any way you can, get them over. Use a firewire drive or something fast.

Part Three: Import Into Mac Mail

A twist to the tale here is that you really have to remember to have made the mailbox folders have notalot of messages. 600 kept crashing mail. 500 did the same. 400 or less seems to work. Kind-of.

Oh, and it won’t import everything at once. So you have to remember how many messages are in each. Best to keep the original computer open and showing the folders to be honest, that way you’ve got a fighting chance of getting it done before the decade’s up.

If you’re importing to another application – say Entourage – then you won’t be able to import all the mail. Do it in stages, because Entourage’s import function dies if it’s got too much to import. But then again, so does Mail.

NOTE: This doesn’t import everything. For some untold reason the mailbox files don’t always have messages in them.

One possible alternative is to:

- add a “.mbox” extention to all the files that don’t have an extension already

- then drag and drop the files individually to the dock icon.

Part four: Import into Entourage (if you really have to)

My job was to get the messages into this monstrosity of an application. I don’t ask questions these days. Really best not to.

1. Close Mac Mail.

2. Open Entourage.

3. Resist urge to punch screen when Entourage plays it’s jolly little theme.

4. From the File Menu, choose Import.

5. In the Import wizard, choose “Import information from a program” and click the > arrow.

6. Choose “Apple Mail” and click the > arrow.

The import may well crash. Keep trying, it’ll usually work on the second try.

7. Tidy the Import folders so they’re meaningful and any crashed import folders are removed. They get numbered which is sorta nice, but it’d be nicer if the import didn’t die. Beggars can’t be choosers though.

8. Hope you’ve got some gin and lemons in the house. Whoops, did I say that?

And there you are. Welcome to my hell.

NOTE: This doesn’t import everything. For some untold reason the mailbox files don’t always have messages in them.

One possible alternative is to:

- add a “.mbox” extention to all the files that don’t have an extension already

- then drag and drop the files individually to the dock icon.

- click OK to import the file to the application.

Migrating the addressbook

Okay, you should do this from Thunderbird again. This is somewhat easier.

Part One: Export the addressbook from Thunderbird

1. In Thunderbird. click Address book.

2. Select the address book to export (in my case it happened to be the one with addresses in it. Don’t laugh).

3. From the Tools menu, choose Export.

4. Give the file a name and choose the appropriate folder, then

• If you’re exporting for Mac addressbook, choose LDIF
• If you’re exporting for Entourage, choose Comma Separated or tab separated.

5. Click Save.

Viola!

Get it onto the mac

Any way you can. This will be a far smaller file, so it’ll be easier.

Import it to addressbook (if you want to sync with another device)

1. Open Addressbook.

2.From the File menu, choose Import and LDIF.

And you’re done.

Import it to Entourage (if you want to use it here)

1. Open Entourage.

2. From the File menu, choose Import.

3. In the wizardy thing, choose Import information from a text file

4. Choose Import contacts from a tab- or comma- delimited text file.

5. Find the file, select it and click Import.

There you are.

Now for the calendar.

Migrate your calendar

Get it out of Outlook

You need a plugin for Firebird for this: Ligntning…

Once the plugin is working in Firebird…

1. Export your outlook calendar as CSV

2. Import the CSV into Lightening.

3. Export as iCalendar format.

Shift it to the mac

Enough said.

Get it into iCal

by the way, you might have noticed the language getting less and less formal. That’s because I’ve been at this all day and just want it to end. I’ve *really* earned this money. Not that I don’t usually of course.

1. Open iCal and from the File menu, choose Import.

2. Choose the .ics file and click OK.

Done.

Import into Entourage

Unbelievable. There’s no way to “import” this, but you can get it in.

1. Select the ics file.

2. Press the Apple (cloverleaf) key and the i key together (get Info).

3. Under “Opens With” select Entourage.

4. Double-click the file…

And you’re done.

For my next job I’ll be juggling snowballs through hell.