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I seem to have a USB connection that's a little flaky and will address it.

When my iPhone, connected to my MacBook made that sound it does when it is first connected a few times in rapid succession, this message appeared.

I snapped a quick screen shot, unplugged my phone and clicked Not Now rather than Learn More, or check Activity Monitor, so I can say much more than "this is how it looked," and no matter how I wiggle the connection I can't reproduce it.

It looks vague and ominously non-Apple, for reasons I can't explain. Is this a standard thing to happen, or is it weird or even potentially dangerous?

enter image description here

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It looks legit, but was probably shown to you by mistake, triggered by the rapid connecting and disconnecting. If you are concerned, you could run MalwareBytes Mac to make sure you have no malware. But that message looks legit to me, unless it's a perfect replica of the real message it is emulating.

  • in what way exactly does it "look legit" to you beyond the fact that it doesn't have a Guy_Fawkes_mask on it? ;-) – uhoh Oct 13 '18 at 11:48
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    In the way that it is a real message from your computer, about your phone. ios.gadgethacks.com/how-to/… – l008com Oct 13 '18 at 11:49
  • okay that would be a good supporting link to add to your answer. Note that my message is unaware of the name of my computer or my phone A software update is required to connect to iPhone, whereas the one in your link contains a name. i.stack.imgur.com/WOSvT.jpg – uhoh Oct 13 '18 at 11:51
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    The context of the message showing up in that link is totally different than how it's showing up for you. I wouldn't worry about it. But like I said, run MalwareBytes if you are concerned. – l008com Oct 13 '18 at 11:53
  • You've convinced me. I've also added a supplementary answer with link and details. – uhoh Oct 13 '18 at 12:09
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I managed to reproduce it again after several tries.

This time I clicked Learn More and was sent to https://support.apple.com/en-us/HT208831

Interestingly, the quoted text there does not even agree with the image there

If your iPhone, iPad, or iPod touch has a newer version of iOS than is supported by your Mac, you may see this alert: "A software update is required to connect to your iOS device. Would you like to download and install this update now?"

Whereas the text in the image is

A software update is required to connect to iPhone.

So if Apple does not find this inconsistency alarming, perhaps I shouldn't either?

Or it may indeed be that the name of my iPhone is "iPhone"!

enter image description here

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    Why don't you check the name of your iPhone and change it to something individual and memorable? (Or have I just missed some sarcasm?) – Andrew Leach Oct 13 '18 at 14:30
  • @AndrewLeach yes, and self-depreciating sarcasm at that. Apparently I've never named my phone, nor needed to know that it could have had one. – uhoh Oct 13 '18 at 14:33

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