iOS not displaying "Trust this device" alert

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iOS not displaying "Trust this device" alert

Our organisation, up until recently, has not had a need to allow devices to pair with any hosts for file transfers (videos), and so we have an MDM policy in place that prevents this from happening.

We now have a requirement to do this, but have no Macs on site (all of our infrastructure, including clients, is Windows based). Therefore creating an MDM policy with a host certificate for host pairing is not available (as far as I can tell, you can't do this for Windows machines).

Didn't think this would be too much of an issue since when connecting an iOS device to a machine, our experience had been up to this point that an alert is displayed to trust the device. If you select to do this, you have to enter the passcode before that device can then access the files on the iOS device.

Unfortunately, it now appears that in order for this prompt to be displayed, the machine has to have iTunes installed. If it's not, there is simply an allow/don't allow prompt being displayed on the iOS device which then doesn't require a passcode to confirm.

Is anybody aware of why this is the behaviour that's being observed? It's been tried on multiple Windows machines with multiple iOS devices. Obviously we can't control which machines these devices are allowed to host with (as per previous comment about no Macs on site) and want to put in place as much risk mitigation as possible for these files.

Any help on this would be greatly appreciated.

Thanks

iPad (6th gen) WiFi

Posted on Jun 27, 2019 3:12 AM

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Answer 1

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Demo

Level 10

166,747 points

Jun 27, 2019 3:35 AM in response to Community User

I can't speak from experience, but according to the Apple KB article, one of the troubleshooting steps to take if you don't see the Trust dialog is to make sure that you are running the latest version of iTunes. The text that I copied below is from the KB article.

About the 'Trust This Computer' alert on your iPhone, iPad, or iPod touch - Apple Support

If you tap Trust or Don't Trust but iOS doesn't accept your answer, or if the Trust alert won't appear, follow these steps. Try again after each:

Make sure that your computer has the latest version of iTunes.

Disconnect and reconnect your iOS device from your computer.

Restart your iOS device and your computer.

Reset your Trust settings.

If the above steps don't help, go to Settings > General > Reset and tap Reset Network Settings. This also resets Wi-Fi networks and passwords, cellular settings, and VPN and APN settings that you’ve used before.

If you downloaded iTunes for Windows from the Microsoft Store, make sure that iTunes Mobile Device Helper is enabled as a startup item.

If you still need help, contact Apple Support.

This indicates to me that having iTunes is necessary.

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Answer 2

Jun 27, 2019 4:04 AM in response to Demo

I've seen that KB article, but as I said in my post - there's no way of controlling whether or not any device that is not in our organisation has iTunes installed on it or not. These are the devices that we are concerned about as the trust alert doesn't display but instead the allow/don't allow prompt displays instead.

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Answer 3

Jun 27, 2019 4:10 AM in response to Community User

It would seem to be a rather large security flaw if the only thing not stopping an iOS device from sharing its files with a host machine is the lack of an iTunes installation on that host machine.

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iOS not displaying "Trust this device" alert

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