Sharing iTunes Store purchased songs with brother

I used to easily be able to send my brother a song file, via email, and he could open it, because he was "authorized" on my account. Lately, when he enters my password, it won't open for him. I double-checked the password and it should work correctly.
Anyone know what else it could be? He should be authorized.

Are you serious? I thought I could have authorized people on my "list" who I can share it with.

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