Is it normal for an iPad or iPhone to ask you “do you trust this computer” every time one connects to it? This is happening to me, and while it’s a minor annoyance, it is an annoyance nonetheless.
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Should only happen the first time.
That’s what I thought. I’m going to try to reset location/privacy data and see if that straightens this out. Thank you.
Please report back if you find out what settings were causing that to happen, I have similar problems with my phone and also with visiting icloud.com! 
I’ve seen this happen from time to time. Sometimes flipping the icloud keychain switch on the iPad fixed the issue. (don’t ask me why, it’s iCloud :-))
It seems that resetting location and privacy fixed the problem for me. I’ll keep my eye on it over the next few days and report back if I start seeing the trust dialog again. If so, I’ll also try @JKoopmans suggestion.
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