I’ve recently been struggling with an issue where iTunes repeatedly prompts for the iTunes store password. There are some forum threads out there that address the issue, but in my case it went beyond the common solutions. I wanted to call out the steps to look for.

This was particularly troubling to me, since I have arthritis; typing any more than I need to can be very painful at times. Also, secure passwords can be a bit awkward to type, since they aren’t normal words.

• Cookies
• Keychain
• Multiple Accounts

So, one of the first things to check is your cookie preferences in Safari. iTunes shares the same cookie storage as Safari and the same restrictions, so if you don’t accept cookies, then you’re going to have trouble. Open up Preferences > Privacy and make sure that your cookie preferences are set to anything other than Always.

Your keychain could be corrupt. Open up Keychain Access, then bring up preferences and “Reset my default keychain”. This will blow away a bunch of saved passwords, so you might want to think about this one first.

Finally, the issue that was causing my trouble. I had purchases under multiple iTunes account. I used Doug’s “Track Down Purchases” applescript to identify what was under my old account and see if it was worth really hanging on to. In my case, it wasn’t, so I purged the files from my old account. Depending on what you have, you can also see about using iTunes match to switch files you own over to your other account. Get iTunes match under your current account, make sure the files from your old account are matched, delete them then download them from iCloud. Bonus is that you’ll probably get better quality copies without DRM.

Good luck!