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EDIT: I've noticed this only occurs when I have hotspot enabled!

Often, when I connect my iPhone7 to my MacBook Pro 2018 (using a new AppleStore-supplied USB cable), the iPhone prompts "Trust this computer?". I tap "Yes", and then have to enter my six digit pass code on the iPhone.

It's happening more than 50% of the time, probably 60-80% from eyeballing.

i.e. Not every time. It's not 100% repeatable. But I've just tried disconnecting and reconnecting 10 times and 7 times I got this prompt.

This is beginning to infuriate me. Is there any step I can take towards diagnosing?

EDIT: It is worth noting that the cable does work. I am able to transfer data between the computer and phone. So it appears the issue is not related to the cable.

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Most likely lint.

The lightning connector is prone to collecting dust and dirt, which can keep the phone from getting a clean signal from the cable (a faulty or not-to-spec cable can have the same effect). Take a toothpick or anything else that's thin and non-conducting and get that dust bunny out.

Never believe anyone telling you to reboot all devices and reinstall all operating systems in your house.

  • A good suggestion. I tried this (by jamming tissue paper in and wiggling it around) but just made it worse -- the phone then wouldn't respond to the cable. I took it to the repair shop who cleaned it out properly. Now everything works again. However the issue persists. – P i Sep 2 at 14:05
  • Small paperclip with (or without) tissue should get all debris out that affects the connector. So should compressed air. If the issue persists, check the cable connections. Try a different cable. I've had this happen with my desktop stand (the Apple one). Over time, i.e. many months, the lighting cable in the back of the stand managed to become loose. Pull all cables and plug them back in. That did it for me. – leclercdumombasin Sep 5 at 4:25

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