Q: iTunes Asks For My Password Every Time It Opens

I think I might have a solution for this as I have had the same issues after updating itunes and OSX.

Itunes is connected to Safari and when I opened Safari and cleared ALL cookies, history cache etc and then RESTARTED my computer and opened iTunes, I only had to log in once and had no issues.

I hope this helps.

For me this maddening issue seems to be connected with Safari cookies as others suggested. Whenever I go to Safari and "Clear History and Website Data" from the History menu or "Remove All Website Data" from the Privacy pane in Safari Preferences, iTunes asks me to login when I open it.

The problem is, it's also tied to Safari cookie preference, also on on the Privacy pane. I hate web cookies and don't accept them unless I need to log in to a web site, but I found I had to enable cookies, at least until I logged into iTunes, then I could disable them. Unfortunately I have to do this same song and dance everytime I clear my safari cache.

My answer to this annoying iTunes issue? Set Safari to accept cookies and then never use it for web browsing since I don't want to accept cookies.

I think its ridiculous that Apple requires me to accept cookies in Safari just so I can use iTunes. It's like some lazy third grader designed their software.

<rant>This is why I stopped using Safari in the first place: they don't have cookie prompting like every other legitimate browser in the known universe, and its current cookie preferences are inadequate to say the least. "Allow from current website only" doesn't do what it says because I always manage to get cookies set for ad trackers and other stalkerware so I just stopped accepting them altogether because I don't always want to accept cookies even from sites I visit. But, since Apple decided to link iTunes with Safari cookies, I can't do that so I stopped using Safari altogether. I would LOVE to take advantage of Safari's Keychain integration and password generation features, but I cannot accept a browser that doesn't allow me to control which sites I accept cookies from. They seem to have adopted a neurotic "dumbing down" mentality in the name of "user friendliness" the last few years, and this convoluted cookie management and iTunes integration is just one example.</rant>

I am going to have to agree.  This morning - without remembering these posts from last night - opened Fire Fox, the other browser I use in addition to Safari - then opened iTunes.   I did not have to sign in one time.  Amazing!  So I then went HMMMM.... So i closed fire fox, closed iTunes, then opened Safari.  I cleared out all cookies in Safari as I usually do (Fire Fox clears all cookies when closed) then opened iTunes.  I had to sign in SIX TIMES!   To go further, I closed Safari, iTunes and then reopened Fire Fox and iTunes.  Did not have to sign in ONCE.

Yep!  Definitely a Safari issue.   

Add me as well. Drives me crazy. I've also had an issue with iTunes Match not allowing me to play songs showing in my iCloud library. I always have to sign out of that and sign back in. Wondering if they are related.

I'm having the EXACT same issue.  iTunes asks me for my password 3x in a row.

Thanks to some previous posters who mentioned that this (really superfluous) issue is related to Safari cookies, I could easily fix it by using a cookie manager. I use Cookie by sweetpproductions.com but there are free ones out there as well in extensions.apple.com Once installed, all you gotta do is set apple.com cookies as favorites so they don't get deleted.

Many thanks, Axeman.

So far (holding thumbs) your remedy (via Get Info) has worked.

May it work for others suffering this annoying iTunes request.

Steve