"Device Timed Out" error in Sidecar

So...trying to setup Sidecar for my supervisor (brand new MacBook Pro updated to Catalina, newest 12.9" iPad Pro updated to the latest version of iPad OS 13), and even though the same Apple ID is on both machines, and even though 2FA is on, we keep getting the same error: "The Device Timed Out." Any suggestions?

MacBook Pro with Touch Bar

Posted on Oct 8, 2019 10:28 AM

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Posted on Jun 2, 2020 5:09 AM

Apart from the list mention in https://support.apple.com/en-us/HT210380

Make sure you don't have any VPN software running and connected to a VPN. Took some time to realised that i had connected to my company vpn on my mac and a private vpn on my ipad. once I turned both off. everything started working.

86 replies

Mar 27, 2020 2:33 PM in response to Kbouressa

A VPN is a private network that I am guessing your child need for access to the college network. If this was a request by the school, they usually can help you set it up, basically it will require:


a) internet connection

b) software provided by the college, if that’s the case

c) username and password to connect to their private network


once that’s done, she will be able to access her math test.


about the brightness, it depends which device you’re on; if you’re using a mac, I usually change the screen’s brightness from the control bar on top of the keyboard. It must be also in the settings.


I hope that helps. Please let me know if you have any other questions.

Apr 29, 2020 6:33 AM in response to cocarco

I'm having this issue too and it's getting a little ridiculous. I have a 2019 16-inch MacBook Pro running MacOS Catalina 10.15.2 trying to sidecar an iPad Pro 12.9 inch (ML0G2LL/A) running iPadOS 13.4.1.


Here's what I've tried and nothings has worked, I still get the same timeout error:

  • Turned on bluetooth for both devices
  • Made sure both devices are on the same wifi
  • Made sure neither device is signed into VPN
  • Restarted both devices
  • Signed out and signed back into iCloud on both devices
  • Turned off Keep Today View on iPad Home Screen
  • Turned off Do Not Disturb on both devices
  • Set both device's display settings to Light mode (and turned off Night shift just in case)
  • Tried turning handoff on and off for both devices and various combinations


At this point, should I start randomly trying other settings to see if any of them make a difference? Any other ideas?


May 2, 2020 8:23 PM in response to cocarco

Here we go, yet another annoying, months old, unfixed bug from Apple as we watch them turn into Microsoft. Brand new 2020 MacBook Air, out of the box today, Sidecar fails. None of these workarounds fixes it. Getting very tired of Apple workarounds anyway. They seem to think that letting users fend for themselves and share bizarre, obscure workarounds that may or may not work counts as some kind of customer service for their (very) premium priced products. Sidecar was a nice idea but the execution is appalling. Generally have to run it on a 5 Ghz wifi or it stumbles - oh yes, another bizarre workaround found from another suffering user. I guess Apple has better things to do.

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"Device Timed Out" error in Sidecar

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