For as long as I’ve been using OS X, Apple has included a set of productivity apps that meet the basic requirements of most users. Power users often bitched about these apps—“I had a contact manager on my Palm Pilot in 1998 that could do things Address Book still can’t”—and a community of third-party developers created plug-ins and pro apps that added the features missing from Mail, iCal, and Address Book. Most users, though, happily used the built-in apps from Apple; they have had a limited feature set, but what they did they did well.

That changed with Lion. Messages, a new app, couldn’t stay in sync, refused to deliver messages on time, and often bungled the message order. Address Book lost its three-pane view, making groups of contacts difficult to deal with. And iCal hid its calendar list, slowed down the navigation between months, and stylized its day numbers to the point where they were difficult to read.1 Mac users bemoaned these regressions and blamed it on unwarranted iOSification.

With the introduction of Mavericks, Apple said all the right things and seemed to be making corrections. The former Address Book and iCal have kept their new iOS-inspired names2 but have returned to a more Mac-like look and function. Messages improved, too, although I suspect that had more to do with backend improvements than with the Messages program itself.

Mail, though, took a nosedive. First, there was its problem with GMail and certain folder settings. I never experienced this because I don’t use those folder settings on my MacBook Air, and I didn’t upgrade my iMac (my main work computer) until well after Mail had been updated. Some people sympathized with Apple on this matter because what Google calls IMAP isn’t real IMAP, and there are booby traps in implementing a mail client that uses it. Even though I didn’t experience the GMail problem, I thought Apple’s failure to work well with what is probably the most popular email service in the world was inexcusable.

Then came the “no retrieval” problem characterized by Apple this way:

For some email providers, new email messages in Mail may only appear to arrive when Mail is first opened. No new email arrives until Mail is quit and reopened.

This one did bite me and is still a problem. And the problem isn’t just with receiving mail. I’ve often found that mail I’ve “sent” hasn’t actually left my computer; I usually don’t notice until much later that the message is stuck in my Outbox. You could argue that the badge on my Outbox is a clear indication that something is wrong, but I’m not in the habit of checking the Outbox. Twenty-plus years of using mail clients that actually send when I hit the Send button has conditioned me to expect behavior that Mavericks Mail somehow doesn’t provide.

Apple’s resolution—which is a workaround, not a resolution—is laughable:

1. Choose Mailbox > Take All Accounts Offline.
2. Choose Mailbox > Get All New Mail.

They want me to manually check my mail throughout the day.3 Like an animal.

So I’m using a mail client that can’t be trusted to send or receive mail. Can it get worse? Yes. I learned this past week that searching doesn’t work, either. Or at least not consistently.

I was cleaning up my Inbox, searching for a client’s name and moving the found messages to a project mailbox, when I realized that many of the messages from that client weren’t being found. In some cases, messages from that client that were visible in the message list didn’t show up in the search results. Relaunching Mail didn’t help; I had to scroll through my Inbox to find the messages by hand. Again, like an animal.

I ran some tests to see if that was some sort of fluke. One of my project mailboxes has over 600 messages in it. The project is an investigation of, among other things, a broken bolt, and I would guess that at least 100 of the emails in that mailbox include the word “bolt.” When I searched for “bolt” in that mailbox I got no hits. Not a one.

The search problem is so bad I suspect there’s something corrupt in a settings file. But I can’t just Trash some plist file in the hope that it’ll solve the problem—I’ll end up destroying something important by mistake. On the other hand, I can’t live with a non-working Mail.

I suppose I’ll end up switching to MailMate, even though my email needs are fairly modest and a working version of Mail would be sufficient.

That, in fact, is the most annoying thing about this mess. Apple has broken the covenant. The deal was that I get a mail client that isn’t fancy but works, and in return I don’t complain about a lack of features I’ll never use. It’s a simple arrangement that’s worked for nine years, and now it’s all this.

Update 2/17/14
Reader John Marshall suggested I rebuild the Mailboxes to get search working. I tried that when I got into work this morning, but nothing changed. Then I rebooted the computer and tried the bolt search again. At first, there were no hits. Then I toggled the search target between Entire Message and Subject. Soon the number of hits for Entire Message was 3, then it changed to 182, and eventually settled on 197. This is, by the way, a mailbox that’s on my local computer, so network lag isn’t the reason for the delay.

While I’m happy to finally get results that make sense, the way it happened doesn’t inspire confidence. I don’t know whether it was the rebuild, the reboot, or the combination of both that did the trick, and the gradual change in the number of matches is disturbing. Maybe there’s some database work going on in the background that will settle itself out in time. Computers are deterministic systems, aren’t they?

1. iCal’s leather, stitching, and torn paper got most of the bad publicity, but it wasn’t just the look of iCal that went downhill. So did its usability.

2. Thanks to Ricky Mondello for reminding me that the renaming was done in Mountain Lion.

3. I’ve written an AppleScript that selects these two menu commands, and I’ve set up a Launch Agent to run the script periodically. I haven’t had it running long enough to know that it works, but when I feel confident in it I’ll post it here.