Password doesn't work the very next time!

I set up my CEO's Apple ID password, but it didn't work the very next time.  (No, he did not change it.)
I reset the CEO's password and created a new one, but it is not working, this, the very next time.  (No, he did not change it.)
Also, posting to this board was unbelievably difficult - I got those spinning gray planks and only briefly saw what appeared to be an input box that referred to a font family and size.  20 minutes of trying everything and I'm finally entering a discussion.

BTW, correct password hint is there, just doesn't access computer.

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