Due to the gravity of the situation this one warrants its own post. Thanks in no small measure to my best friend ‘Sheer, Dumb Luck’, I stumbled across a solution for my problem last night.

And somehow I suspect this solution might just be general enough in nature that it might help other folks affected by this or similar issues as well. Here’s a brief summary of the problem:

Single or multiple devices running OS X or iOS are no longer able to purchase (or download for free) items (apps, music, etc.) from Apple’s iTunes Store. Before being able to complete any transaction, the respective user is always asked to verify his credit card information (usually a missing security code) only to get stuck in an endless loop somewhere along this dialog. More detail available in this post.

Following my one hour long conversation with Apple Support yesterday, I had an epiphany. Oh alright, maybe ‘epiphany’ is a bit strong of a word — how about ‘a moment of sudden revelation or insight’ instead?

Somewhere along the line of the conversation, Jay the friendly Apple Support employee had mentioned something to the tune of: “It (iPhone 4) is no longer trusted, that’s why you are getting this error”.

After explaining this, he had me sign out of my iTunes account on the iPhone, delete my credit card info from within the copy of iTunes running on my desktop machine, and then made me sign out there as well (a Mac Pro running Mac OS X 10.6.4).

Thereafter, with no credit card on file and signed out on all devices (iPhone 4 and desktop Mac), he made me sign back in on the iPhone and then attempt to download an application upgrade from within the App Store app. Lo and behold, that worked — partial success!

I then made him stay on the line with me while I re-entered my credit card info using iTunes on the Mac Pro. After having done that, I tried the iPhone again and the error loop was back — ACK! At that point Jay pretty much gave up on me, or the iTunes Store, depending on how you look at it, and we hung up soon thereafter.

A few hours later, it struck me … “Your iPhone 4 is no longer trusted, that’s why you are getting this error” … well, what could I possibly do to get the iTunes Store to trust my iPhone again?

Enter the credit card information directly on the untrusted device — Eureka!

Thus, I proceeded as follows:

  1. Remove whatever credit card info you have on file in the iTunes Store (‘iTunes Store’ > ‘View my Account’ > ‘Edit Payment Information’ > ‘None’), so that under ‘Payment Information’ it says ‘No credit card on file’.
  2. Once you have removed the credit card information, sign out on all your devices (OS X: Menu ‘Store’ > ‘Sign Out’, iOS: ‘Settings App’ > ‘Store’ > ‘Sign Out’)
  3. The following may not be strictly necessary, but it is what worked for me so I suggest you take this step, too — it can’t hurt anything: Reboot all your devices
  4. On the ‘untrusted’ device (for me: the iPhone 4), sign back in to your account (‘Settings App’ > ‘Store’ > ‘Sign In’).
  5. Still using the ‘untrusted’ device, tap/click in ‘View Account’
  6. Again, still using the ‘untrusted’ device, re-enter your credit card info.
  7. Lastly, sign back in on all your other devices, computers, etc.

Voilà, this did the trick for me — I have been able to download items from the iTunes Store with my iPhone 4 ever since.

Three cheers for epiphanies!!

OS X, make sure iTunes displays this before signing out

iOS, make sure Settings app displays this before signing out

I hope this’ll help you as well. Feel free to ask any questions you might have in the comments, I’ll be happy to help if I can.

Update: Make sure you take a peek at Berko1’s comment below. Apple changed the store policies again, and you’ll have to agree to the changes as outlined by Berko1