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I have been trying to use Sidecar in the public betas of macOS Catalina and iPadOS 13.

I have a 2019 Macbook Pro, and a 3rd generation iPad Pro, so I know I have supported devices.

Both devices are on the same Wifi network, and both have Bluetooth enabled.

Both devices are logged into iCloud with the same AppleID.

Both devices have two-factor authentication enabled.

I have tried this both with and without a USB-C cable connection between the two devices.

The Sidecar preference pane in System Preferences does appear, and when I go into it I can see in the "Select Device" dropdown that my Mac can "see" my iPad Pro.

However, when I try to connect to it, I get the following after a pause:

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I keep watching this page for troubleshooting tips, but none have been useful for me thus far.

FWIW, I have been a "good citizen" and reported my problems to Apple via the Feedback Assistant apps on both devices, so in case this is a temporary bug, I've reported it. I'm just asking here in case someone else has encountered this issue.

Edit: Eventually, Sidecar started working for me (sometimes) after some of the later public betas came out. I'm not sure exactly which version(s) of Catalina and/or iPadOS made the difference for me. So far it has worked without any timeouts in the final versions. I didn't need to downgrade and then re-upgrade as the submitted answer suggests, although I'm glad that has worked for some.

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I had a same problem and I have just solved the problem. Just reinstall the iPadOS13.1 after downgrading to iOS 12.4.

Here is the guide for downgrading. Remember to backup your files, then install ipadOS 13 normally in Settings -> General -> Software update.

  • Hi, welcome and thanks for the answer! Setting up previous major release.. is it straightforward? Could you link something on how to do it please? – ankii Sep 30 at 11:01
  • gottabemobile.com/how-to-downgrade-from-ipados-13-to-ios-12 Here is the guid. Remember to backup your files, then install ipados13 normally and.. that's all – EnvyVu Sep 30 at 17:26
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I suspect that this is a very generic error message and that not everyone who is experiencing it is encountering the same root cause.

I just experienced this error after successfully using Sidecar all day long at work.

After I came home, I logged onto my work's VPN to check on something and, after some amount of time, Sidecar disconnected. When I tried to reconnect it, I got the same "The device timed out" message.

On a hunch, I disconnected from the VPN (in the FortiClient app that my employer requires for VPN access) and Sidecar worked again.

Bottom line: using a VPN can cause this symptom.

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