Flex ID

I’ve ignored updating a bunch of the apps I’ve downloaded to my iPhone for some time. Most are free apps, and a few I’ve paid for. So, iTunes says I’m now up to 21 “free” updates to install, and I finally decided to download the updates. What did I get? This lovely dialog:

How many things can you count that are wrong?

1. The headline is crazy long.
2. The detailed description is exactly the same as the headline.
3. That’s terrible writing. “Can not.” Really? And “…you have not owned the major version…” Huh? Hire a writer.*
4. There are no choices offered – just “OK.” But it’s not okay; can’t you offer me a choice to resolve the problem?
5. Not only is the dialog not offering to fix the problem, it doesn’t even give me enough information to fix it myself. Which app is it that I can’t update?
6. Because there was one offending app, iTunes didn’t update any of them.

This is pure stupidity, and surprisingly common. Why is it that software usually stops everything at the first sign of trouble and refuses to proceed until each problem is resolved?

I had a similar problem with copying files from my Mac to my PC recently – whenever Windows had trouble copying an individual file, everything just stopped and I was presented with a non-specific error dialog. I forgot to get a screenshot, but the gist of it was: ‘There was a problem copying some file, but I’m not going to tell you which one, and I’m just going to stop copying the rest of the files. OK?’ I was trying to copy a large number of files, and so each time this happened, I had to manually compare the file lists to figure out where the problem was, and manually restart the copy (starting with the next file in the list). Totally obnoxious.

So, here’s my advice for how your software should handle batch operations:

• If you can quickly assess problems at the start, do that. But (a) report the specific problems, (b) provide options to fix the problems if you can or at least specific instructions on what to do if you can’t, and (c) provide an option to skip the problem areas/files and proceed with the rest of the operation.
• If you can only identify problems along the way: (a) skip the problems as they arise, (b) proceed with the rest of the operation, (c) present a message at the end with a specific list of all the problems you encountered, and preferably (d) provide options and/or specific instructions to fix the problems. Alternatively, report the problems as they crop up, but proceed with the rest of the operation in the background.

* OK Apple, some free advice on how to at least fix the writing in this dialog:

• Headline: There was a problem downloading one of the updates
• Details: You cannot download the update for [app name] because you haven’t purchased the most recent major version.
• Checkbox (checked by default): Don’t remind me again for this version of [app name]
• Buttons: Learn about the latest version; OK

I got this message when I recently ran the software update (while iTunes was running) to go from iTunes version 8.1 to 8.1.1.

Unfortunately, the developers weren’t smart enough* to figure out how to do an update gracefully (in the background, without quitting iTunes, and more importantly without forcing me to do the work). I know this is possible, because anything is possible with software (that, and the Firefox developers have figured it out). I’m sure it’s hard, and it would be boring work for the team, but is that really my problem? If there’s a choice to make between developers doing more work or users doing more work, I think the developers should have to do the work. A handful of developers would only have to do the work once, but instead they have passed the buck to tens (hundreds?) of millions of unsuspecting iTunes users.

The really galling thing about this dialog box is that the text clearly shows that they know exactly what needs to happen but they are unwilling to assist me. For some reason I have to read some annoying message, go quit iTunes on my own (and wait for it to close “completely” – how am I supposed to know what that means?), return to this dialog box to click Continue, wait for the update to finish, then relaunch iTunes. Just throwing the word “please” in there at the beginning doesn’t make it polite to order me around like this. Even if Apple can’t do a graceful update, couldn’t they at least do all that stuff when I click Continue?

* I don’t really think that their developers aren’t smart enough to figure this out, but someone at Apple is to blame. I imagine “graceful updating” is on a long backlog of features to implement, but it never bubbles up as a high priority because there’s a workaround.