I had to fill in a PDF form using Adobe’s Reader and had problems with the file. My copy of the Reader application complained it was older than what the document was intended for so I decided to update the app. Here’s how not to implement software updates. I guess this could be called a “install a Reader Update Game”.

1. Started up Reader 6.0, updater pops up and tells me to update to 6.0.6
2. After installing the update, Reader starts up and tells me I should install update to 7.0
3. 7.0 installer wants to quit some applications while it updates. After it’s done, I get recommended I should install updates to versions 7.0.5, 7.0.7, 7.0.8 and 7.0.9. I now have 6.0.6 and 7.0 installed.
4. Instead of installing all the updates, the 7.0.5 installer creates a new Reader copy named Reader 7.0.5.app and stops the update process. I now have versions 6.0.6, 7.0 and 7.0.5 installed.
5. Updater now recommends I install critical security updates to versions 7.0.7, 7.0.8 and 7.0.9.
6. After the update, the application’s name is still Reader 7.0.5, Finder also claims it’s that version but Reader thinks it’s 7.0.9. The updater application still wants to install the “full” 7.0.7, 7.0.8 and 7.0.9 updates. Trying to update the software fails since the updates aren’t compatible with the semi-updated installation.
7. Decided to give up and go to adobe.com to download the latest version which turned out to be version 8!
8. Downloaded the downloader which fired up a Reader Download Manager which fired up the installer.
9. Reader 8.0.0 installed, just one update left anymore. I now have Reader 8.0.0 with Language Support. Threw the three old versions to trash. Reader now actually works and is pretty fast.

The question remains, why didn’t the first update notification tell me version 8 was available? In my view the process took seven (long) steps too many.