"Device Timed Out" error in Sidecar

The new MacBook Pro and iPad Pro with fully updated systems - as many other users the iPad gives time-out when trying to connect it using sidecar.

Considering the costs of these devices I find this unacceptable, time to switch to different more reliable company ....

After struggling for the longest time, what helped mine work (both wired or wireless) was to make sure that both device's keychain access are turned on. From my experience, Mac is trying to connect to iPad, iPad is trying to verify mac, if mac does not have keychain turned on, (mine wasn't) then it enters an infinite loop, which will end up with "Device timed out". Hope this helps someone. Cheers

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?

Make sure that Handoff is not checked on both the iPad and the Mac.

To Disable Handoff on your devices

• iPad, iPhone, and iPod touch: Go to Settings , then tap General > Handoff.
• Mac: Choose Apple Menu > System Preferences > General, then turn off “Allow Handoff between this Mac and your iCloud devices.”

(From: Support.Apple)

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.

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.

I got this off a post on macreports: Please try the tips above. If nothing works, reset your network settings on your iPad by going to Settings > General > Reset > Reset Network Settings.

Tried the 10 other steps on that post before this, most of which are in this thread, to no avail. This last one was the only one that worked. Had to set up wifi networks again afterwards. New 2020 MacBook Pro, new iPad Pro, get your act together Apple and stop turning into Microsoft.

Not sure if the issue still remains for you. But in case others need solutions..

Enter in your password at System Preferences > Apple ID > Overview.

It will say that your Mac needs to update Apple ID settings in order to allow you to fully use iCloud(or Apple)'s services.

I can assume that Sidecar is definitely one of its services.

Hope this helps.

Hey cocarco,

Thank you for using Apple Support Communities!

I see that you're having issues with Sidecar timing out. I'd like to help out.

First, I'd like for you to restart both devices and confirm these steps are set up:

Restart your iPhone, iPad, or iPod touch - Apple Support

Use your iPad as a second display for your Mac with Sidecar - Apple Support

Cheers!

This totally did the trick for me. 2019 MBP 15in i7 and 12.9in ipad pro 2019. couldnt get it to connect after the first time. Tried signing in an out of apple id several time. turned off Today View and everything worked flawlessly.

No luck for me - MBP w/ Catalina 10.15.7, iPad Pro w/ iOS 14.5.1. Toggled bluetooth, handoff, restarted both, signed in / out of iCloud on both, same wi-fi, logged in w/ 2FA enabled. Still getting the 'Device timed out' error.

After trying every suggestion I found on the web, this solved my problem:

Go to iPad settings, at the top of the menu under your apple id, there is a warning which says ''update apple id settings''.

After clicking on it and following the instructions, sidecar worked for me, wirelessly.

Hope that helps

Restarted both iPad and MacBook. Both connected to same wifi, both bluetooth enabled, both running latest OS. Can see MacBook offering to connect to sidecar, just get device timed out error. Works with a cable though, but back to front if you know what I mean, uses the MacBook as secondary display. Works fine with my iMac. Any other ideas?

I've been following this thread for a while as I too was having the same difficulty. I'm not sure if you were ever able to figure this out, but I just discovered that if you are connected to a network via VPN, then you will get this error. As soon as I shut down my VPN connection, I was able to get my iPad to act as a secondary monitor.

Something related to the Today View must be causing the initial time out issue. I had "do not disturb" on, turned it off, and it connected to the iPad. Turned back on do not disturb and seems to be working at the moment. This was after signing out of iCloud on both devices, rebooting and signing back it ... and it still not working. Though before signout, the option to see the iPad didn't appear at all. After signing out and back it, at least the option appeared in the Display dropdown, but then the time out issue occurred. Messing with the Today View seemed to unhitch the problem for me.