iPhone app updates always fail

This morning iTunes told me an update was available for the SportsTap application. I downloaded the update, then set my iPhone in its cradle for syncing. As I expected, the update failed with a message to the effect that the installation of SportsTap on the phone had failed (I forgot to take a screenshot of the error message).

This happens every time an app is updated. I first noticed it with OmniFocus and thought the problem was part of OmniFocus’s teething pains. But now, with a few more weeks of experience under my belt, I see that it’s an iPhone/App Store problem, not an OmniFocus problem.

This bug makes updating an app a four-step process:

  1. Download the update in iTunes.
  2. Sync the iPhone and get the “installation failed” error message.
  3. Uncheck the app in the iPhone’s Applications tab in iTunes and resync to uninstall the app.

  4. Recheck the app in the iPhone’s Applications tab in iTunes and resync to reinstall the app.

Since I know the update is going to fail, it would be nice if I could bypass Step 2. Unfortunately, the iPhone has to be connected to do Step 3, and because I prefer to have my iPhone set to sync when connected, the failed sync of Step 2 happens automatically.

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