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This one drove me ABSOLUTELY CRAZY!
I was responding to a customer complaint when I ran across this one. She said that every time she tried to buy an audiobook (or any thing else for that matter) from the iTunes store, she was getting the following error message:
Session Timeout
Your session has timed out. Please try this operation again from the beginning.
The iTunes message was almost immediate, so I knew that it wasn’t a REAL session timeout. It seemed very much like a glitch in the software. I thought about reinstalling the software, but I thought I would try a few other things before I resorted to a reinstall of iTunes.
I should probably mention right now that I was on a Mac Powerbook G4… Not a Windows PC.
So, I searched the web and found numerous articles, forum posts and Yahoo! questions that referred to the same “Session Timeout” error message.
Most of them mentioned a common problem with the time application, time synchronization, and the time zone. So, I tried all of these.
First, I confirmed the time was correct… It was.
Second, I changed the time to a few hours into the future, tried iTunes again, and then changed the time back to the correct time. Then, I tried iTunes again with no success.
Third, I confirmed the correct time zone was set. It was. But, I had also ran across a snippet on a website where someone claimed they found success in changing the time zone to A DIFFERENT time zone and then changing it back. I tried this, but it did not solve my problem.
Then, I got to thinking about what would cause an immediate “Session Timeout” in iTunes. The only other thing that I thought MIGHT be to blame (besides a broken application file somewhere) would be network settings.
All the network settings looked okay, but just for grins I decided to change the DNS settings to something else.
I used the OpenDNS servers:
208.67.222.222
208.67.220.220
Then, I tried the iTunes purchase again…
Eureka!!!!
This seemed to do the trick. I don’t know why the standard DNS server wasn’t doing the trick, but there was obviously some sort of malfunction, either at the ISP level or somewhere else along the way to iTunes.
So if you are getting the following error message:
Session Timeout
Your session has timed out. Please try this operation again from the beginning.
Try the time server and time-zone stuff, and see if it works. If it doesn’t, try changing the DNS settings before completely pulling your hair out.

