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:

enter image description here

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.


I had this problem setting up a new computer. For me, what fixed it was going into Settings > Accounts > iCloud and checking KeyChain

It said I needed to update my account security and prompted me with a few security questions. This seems to have indirectly solved the problem; perhaps some minimum standard of security was not upheld and was causing quiet failure.

Unfortunately, I'm guessing that this won't solve everyone's problems as it seems to be a pretty generic message as mentioned above, just thought I'd add my solution to the pile for everyone who's going down the list and trying everything.

  • This was the only 'solution' that did the trick for me, thx a lot! – z00bs Feb 21 '20 at 15:15
  • I get fixed by following this instruction. Thank you! – Quar Feb 26 '20 at 3:38

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.

  • Can confirm that Turning off the VPN solves this isssue for me. – narayan May 14 '20 at 11:00

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? – anki Sep 30 '19 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 '19 at 17:26

I encountered the same hardware and issues. All I had to do was disconnect from VPN (not close) and it works.

  • No restart or anything special.
  • FortiClient as well.
  • Welcome to Ask Different!. Please refrain from adding comments in an Answer. The preferred way of saying 'thanks' around here is by up-voting good questions and helpful answers (once you have enough reputation to do so), and by accepting the most helpful answer to any question you ask (which also gives you a small boost to your reputation). Please see the About page and also How to Answer. - From Review – fsb Feb 12 '20 at 19:50

I had the same problem. I signed out from Apple ID in my Mac and signed back in, then tried to mirror the screen to iPad. Now the error was changed to Miscellaneous errors occurred. Then, restarting the Mac fixed the issue.

If the AirPlay icon itself is not displayed, Then we have to make sure below things in both iPad and Mac.

  • Bluetooth is On
  • Connected to same WiFi
  • Connected with same Apple ID account
  • Hand Off is enabled
  • +1 This solved the problem for me too. Didn't have to reboot. – Jarle Tufto Aug 14 '20 at 13:38

I had the same problem and here's what worked for me:

On the iPad go to

settings > wi fi

and then chose your wi fi connection and disable the private connection box.

  • iPadOS 13 doesn't support private WiFi connections but your answer may help people experiencing the same issue with iOS 14. – nohillside Dec 27 '20 at 13:35

Test turning off the Today View on the iPad.

Go to Settings then Display & Brightness or Home Screen & Dock and toggle off Keep Today View on Home Screen

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