While most sensible Mac users were looking forward to cool new features in Leopard like Cover Flow, Quick Look, and Time Machine, I was sitting on the edge of my seat, itching to try out iCal and Mail.app's new to-do list integration. I agree with Merlin's approach to using a bunch of single-purpose applications that are very good at what they do instead of a bloated piece of do-everything-ware like Outlook--"a series of super-sharp paring knives over one monstrous Swiss Army Knife"--as he put it, but I looked forward to a little bit of teamwork between two of the applications I use the most. And boy, am I disappointed.

I've professed my love for iCal here repeatedly, but the biggest reason I like it is that I can manage my entire pile of stuff within its colorful, round-cornered confines. I keep my projects and responsibility lists there, my someday/maybe items, all of my next actions. I litter the calendar with reminders and subscribe to my favorite teams' schedules.

I never felt the need for super-tight integration with my email before; if something important came via email, I usually banged out a corresponding to-do item, and filed the message away where I could find it later. I start to get twitchy when I have to look in too many different places for my stuff, which is why I've always turned away from high-powered task managers like OmniFocus. To me, what I have to do consists of my calendar and my to-do list, and I want that all in one place.

That being said, I was intrigued by Leopoard Mail.app's new ability to create to-do items directly out of an email, partly because I have a fetish for that stuff, and sadly, because it looked cool. So the first thing I did after installing Leopard was try it out. That's where the problems began.

The To-Do Two-Step

The initial import of my context calendars and to-do items from iCal seemed to be static. If I made changes to them either in Mail or iCal, nothing synced between the two. If I created a new item it worked, so I chalked it up to an upgrade issue, but I noticed later that to-do items I created solely on local iCal calendars wouldn't disappear from Mail's list if I deleted them from iCal.

Next, I tried creating a to-do item from one of my emails, which, forgive me for being slow, was confusing at first. I thought I could just select a message, click the to-do button, and assign a description. This is at least the way I've thought about email tasks in the past, something like "Call Joe to talk about Mary's email," which refers me to said message, not necessarily a specific sentence in it.

Instead, to create a to-do from Mail, you have to select a piece of text from your message, which then becomes your task description. This is all fine and dandy if it was easy to edit that text to suit your needs. But how often does someone email you a perfect explanation of what to do? Right. So once I figured this part out, I tried editing the description, but Mail would repeatedly skip back to the beginning and replace what I typed with the original text. Sometimes it took me two or three tries to get it right.

I believe this has something to do with my Mail set up. I pipe everything through a Gmail account, which I now check via IMAP. In this arrangement, Mail actually stores the to-do items as messages in your mail account. In fact, every time you sync you Gmail account, Mail writes a new version of the message. I didn't realize this until I looked at my Gmail archive and saw seven copies of each to-do.

I did some unscientific testing by watching the activity window in Mail, and I think that when I started to create a to-do item out of a message, Mail immediately synced with Gmail. If I tried editing the description before it finished, it replaced my text with the original version, now living on the server. I realized I could prevent this from happening by waiting a few seconds to edit, but c'mon, that isn't why I use a Mac. The same thing happened if I created a new to-do item in iCal and tried to make a quick change.

To make matters worse, Mail seems to get confused about discrepancies between the local and server versions of these to-do "messages" very easily. A dialog box asking me if I wanted to keep the local or server version popped up repeatedly, and would loop endlessly unless I chose the server version.

Calendars, Calendars Everywhere

Another problem I encountered is how Mail and iCal allocate their calendars. Like many GTD-centric iCal users, I make separate calendars for different to-do lists. But Mail doesn't see these calendars; instead, you have to create separate ones that live within the mail account.

I tried to get around this limitation by creating mail to-do's in a temporary calendar then moving them to my main ones, but if you move a to-do item from one calendar to another with a different name, it breaks the link to the mail message, which defeats the whole purpose of this tortuous exercise. The only workaround I see is to create duplicate sets of calendars in both iCal and your mail account. If you move to-do's between calendars with the same name, the link is preserved, but again, I use a Mac so I don't have to do shit like that.

These special mail calendars also can't sync with iPods through iTunes. Maybe the forthcoming Leopard version of Missing Sync for Blackberry, Palm, and Windows Mobile PDA users will tackle this, but there's no reason they should have all the fun. I know the iPod's PIM features don't exactly get people rioting on the streets, but on that mythical day when the iPhone gets a to-do list and syncs it through iTunes, one would hope that this gets fixed.

As useful as they might be when you can actually create one, to-do's with attached mail messages also screw up my new favorite trick, the aforementioned "Ass Pocket of iCal." If you print your to-do list, and any of the items have attached messages, iCal tosses either a messy local URL or huge block of ASCII gobbledegook in the notes field. This is a cosmetic problem that irritates a particular sore spot for me, I know, but it's just another item in a long list of disappointments.

Do Over

I won't go so far as calling Mail.app's to-do functionality half-assed, but it also appears to be tacked on as an afterthought. I might have complicated matters by throwing an IMAP account into the mix, but I can't imagine that Apple doesn't have software testers on staff who think about this kind of stuff. But then again, maybe I'm asking them to cater to too specific a need. Mail does offer some nifty hooks into iCal, like recognizing dates and times and letting you create a new event, but the rest of its integration is just confusing and messy.

By itself, Mail's to-do's work fine, and if you feel the need to liberate lots of actions from messages, maybe you should consider doing most of your work there. But if you're a heavy iCal user like me, or find yourself thinking about getting some hot Mail-on-iCal action going, you need to wait for Apple to try again.