Sidecar Not Working; "Unable to Connect to "[iPad Name Here]" & "The device timed out."

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Sidecar Not Working; "Unable to Connect to "[iPad Name Here]" & "The device timed out."

I updated to macOS Catalina, and I was excited to use Sidecar again--I had previously tested macOS Catalina Public Beta, but it ended up corrupting my hard drive--so I attempted to launch the operation, first wirelessly because it was an option, and it gave me the "The device timed out" message. I then tried it again with my USB-C to Lightning Connector cable, and got the same result. I don't know why this is, and I'm looking for input or people with the same problem. I'll leave some information on what devices I'm using below, and some visual evidence.

Mac:

2018 MacBook Air

macOS Catalina 10.15

iPad:

iPad Pro (2nd Gen.) Wi-Fi+Cellular

iPadOS 13.1.2

https://www.youtube.com/watch?v=Fx5g3VfmKoM

MacBook

Posted on Oct 13, 2019 8:06 PM

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Answer 1

chris_g1

Community Specialist

Oct 18, 2019 3:24 PM in response to Jonox9000

Hello Jonox9000,

Thanks for asking the Apple Support Communities for help with Sidecar.

1. I recommend restarting both devices.

Restart iPad - Apple Support

How to turn your Mac on or off - Apple Support

2. Toggle Handoff off and back on for both the source and destination devices. Then toggle Bluetooth off and back on for both the source and destination devices. This article will help: Use Handoff to continue a task on your other devices - Apple Support

3. Test with a wired and wireless connection. Use your iPad as a second display for your Mac with Sidecar - Apple Support

4. Reset user permissions: Resolve issues caused by changing the permissions of items in your home folder - Apple Support

5. Test in a newly created unmodified Mac admin test user: How to test an issue in another user account on your Mac - Apple Support

Be sure to configure the new user is set to use the same Apple ID as the original admin account.

If you need help after these steps, please let us know if you are receiving any alerts about 'iMessage or FaceTime Activation Failed', or if the connection worked wired or not, or if it worked in the test user. Thanks and have a wonderful day.

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Sidecar Not Working; "Unable to Connect to "[iPad Name Here]" & "The device timed out."

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