Mail search and “smart” mailboxes in Mac OS X Lion the biggest promise and the biggest letdown

Correction! Contrary to what I’ve ranted below, it turns out mixed logic is available in Mail search, for those willing to type it out (as it has always been for Spotlight searching). My error arose from the fact that it it is tricky enough to do (enough ways it can break) that it’s pretty easy for repeated efforts to fail, and so much of my discontent with Mail search remains: in particular, a mixed logic search cannot be saved, and there are no tokens available for some pretty major options.

I’ve already had a general rant about’s inadequacies and glitchiness. This is a very specific rant, about Mail’s new search features. The hope of improved searching of my vast mail archives was one of the best reasons I had for upgrading to Lion. I deal with a steady stream of customer inquiries all day long, every day. How easily I can locate old messages = surprisingly key factor in my sanity. It truly makes a difference to me!

Sadly, Lion’s Mail searching is still not particularly good. Improved, yes. Nowhere close to “great.”

The missing logic is illogical!

Most painful to me of all is that Mail remains incapable of mixed/nested boolean logic for either searches and/or smart mailboxes … a maddening limitation for a power user. Mixed logic really needs to be in more apps (not just Mail): the syntax can be invisible and harmless to beginners, but its absence is exasperating to those of us with the dazzling mental prowess required to understand:

something AND (this OR that)

AWOL logic options in the new Mail is all the more frustrating since Apple conceded the value and essential do-ability of nested logic by making it available to the illogical masses in iTunes quite some time ago. Arguably, nested logic is much more useful in Mail than it is in iTunes. It’s certainly welcome in iTunes, but I don’t need genuinely smart playlists to get through the working day.

But in Mail I actually need smart mailboxes showing me everything from both Peter or Paul and not Mary. Simple logic, still impossible in Mail — this is not the stuff of a major upgrade. Thus “smart” mailboxes continue to seem amazingly useless to me.

(Still) literally no logic at all when looking just for folks

No boolean logic at all is available via the search field when searching for people: the UI defaults to “all” searches, so if you search for “from:bob from:susan” you are only going to get messages from both of them — logically impossible, since messages can only have one sender — and there is nothing you can do to change the search to searching for mail from either of them … not just a typical goal in searching, but probably in the top five, maybe the top three. This seems so insultingly simplistic to me that I am inclined to dismiss Mail’s new “improved” search functionality as a joke right out of the box, despite a variety of other niceties.

Another consequence of this, and another weird failure to understand common usage patterns on the part of Apple engineers, is that there is also no way to search for all mail in a conversation: that is, all messages to and from a given person. A search token (to and from) representing that logic would have earned an appreciative whoop from me. Alas, no. When I realized that no such search was possible, I aimed an eye roll and a groan at Cupertino instead. Apple couldn’t anticipate that folks might want to search for all mail to and from certain people? That never came up in a meeting? Don’t they have spouses? Mothers?

Stranger still is that the same logical limitation applies to smart mailboxes, and it remains impossible in that context as well. I still can’t make a smart mailbox for all mail to and from my wife or parents, for instance.

A couple more miscellaneous eye rollers

Busted phrase search. Tragically, the new search also ignores standard phrase search syntax (placing search terms "in quotes" to indicate that you are search for those words in that order, and not just any occurrence of any of those words). So for instance: “subject:hello” finds a message with the subject “hello from typo girl” but “subject:"hello from"” does not! WTF, Apple? That is another particular disappointment.

Painfully missing “to” search. In a classic example of computers trying to be so helpful that they end up doing the opposite, “to” searches are mysteriously concealed from me as an option when I search a mixed “all mail” folder of messages to and from (a very important folder in Gmail), unless I explicitly type it. This doesn’t apply if I’m searching the “Sent” folder, where Mail helpfully and correctly (hey, a word of praise!) assumes that I am probably searching for something I've sent to someone. To do a “to” search of all mail, though, I have to start with “from” … and then tediously change it to “to”! For instance, if I start typing my surname, Mail quickly coughs up several “people” suggestions, starting with “sender contains ‘ingraham’”, but not “recipient contains”. The list also populates with matching names, but if I select one it defaults to a “from” search, and then I have to do precise work with a mouse to change it to a “to” search. So much for an improvement in usability and efficiency.


Search in is still not a bicycle for my mind. More like a unicycle.