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Since I've had the same problem for a month or more, I asked the manager in an Apple Store. The answer: "It's a security feature. Apple changed it on purpose."

I doubt that. It's clearly a bug.
 

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Finally, they fix this issue with 9.0.3:).

Version 9.0.3:

Provides a number of important bug fixes, including:

* iTunes no longer ignores your "Remember password for purchases" setting.
* Addresses problems with syncing some Smart Playlists and Podcasts with iPod.
* Resolves a problem recognizing when iPod is connected.
* Addresses issues that affect stability and performance.
 
This is a huge PITA. But not only here. I have a podcast subscription that requires a password. Every two to three weeks I have to re-enter the damned password. What a pain!
 
I'm having a problem that I think is the same thing. I get most of my TV Shows from iTunes store and subscribe to seasons for some of it. Used to be I could get the shows to download automatically when they were available - now I have to click the "Check for Available Downloads" button every time - and it prompts me to type my iTunes store password twice. It never did this before the last month or so. Very annoying - feedback sent to Apple.
I'm thinking they created some kind of session timeout that's started to bite people.
 
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