How to fix itunes error -206?

Whenever I search, try to buy, or attempt to log in to the iTunes Music Store, I get an error -206 with no detailed text. Many times, lets say about 25% of the time, I get a message saying the store is too busy. I have been getting that for two weeks now, so I think there is a problem in iTunes connecting to the store. Everytime I try to search the Music Store, I get this error. The worst part is if I buy a song or album, I get the -206 error and am unable to download the songs, but I paid for them. I need to go to another machine to download them. I have deleted all iTunes preferences as advised in some forums but nothing seems to help. One more wierd thing I notices is when I try to update the metadata of the files in my library on an external drive, I get teh same -206 error. It pissed me off.

If I try to add the artwork manually I don’t see the error however the artwork does not seem to get set. Googling reveals a few people have various problems with iTunes 10.2 and artwork. I came to the point of understanding that this error is due to an internet connection issue between the iTunes and the music store. Finally, I figured out I get the same error when I am using the Internet through a Proxy. When I checked “Help > Network diagnostics” it reported no errors as if the internet connection to the store is fine but I get the (-206) error when trying to search or play from the iTunes Store. I got rid of the problem by disabling anonymous proxying so that the proxy would pass all header info to the iTunes Store. Before that the proxy would only pass Host, Authorization and Cookie header information. I suspect that there are specific Apple headers which need to be passed through the proxy server otherwise iTunes won’t work properly. So, finally I got rid of that dreading iTunes error -206.

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