The device timed out- sidecar

I was facing the same problem and I tried following things and it seemed to solve the problem

1. Log out Apple ID from both the devices and restart
2. Reset settings in iPad and restared
3. Shared file using Airdrop from Mac to iPad and than iPad to Mac

After doing these three I was able to get it however it was not a very good experience.

Hello there!

I keep having this problem on and off, what I worked out fixed it was I send a photo through airdrop, then they "see" each other again and then the connection works. Sometimes I turn bluetooth off and on quickly on my mac first, but I don't usually need to! No big resets required! Hope this helps!

I finally decided to do a full restore to factory settings from iTunes then restored a backup and it works fine now. I was having other issues with my iPad and this seems to have fixed those as well.

I signed out of both devices and then signed in again. Did not work. However, I restarted my iMac and that did the trick.

It took me 24 hours with a combination of: juggling Apple TV settings allowing everyone to connect/resetting iPad Pro/restarting MacBook Pro. Had to repeat some of these steps. Have no idea why Apple TV should be involved but it is now working. (Apple TV off)

Wi-Fi connection still doesn't work for me, but the following seemed to work to get Sidecar work with my iPad Pro via standard lightning cable connection.

I tried dozens times to connect it via cable to my iMac and MacBook, and nothing worked. Then I tried to plug in a lightning cable ti iMac (or MacBook) first, and then to iPad, and it worked. It happened on both iMac and MacBook, and now works both ways.

This shouldn't be voodoo, Apple, but there you are.

Interesting continuing discussion. Since ensuring I am on the same network, Bluetooth on (relevant?), and that the VPN I am using is turned off there have been no issues. The VPN should not be an issue as it is configured to allow connections within the same network. Confusing.

I have the same problem, then realised I am using a VPN. Disconnect the VPN, and everything worked perfectly............

I have the same problem. Only extreme measures work. I have to reboot both my MacBook Pro (running the latest 10.15.1) and my iPad Pro (running the latest iOS 13.2.3). And then connect the cable, and finally hope and pray it works, which it then does 2 out of 3 times. It does not work on Wi-fi (I checked and double checked I was on the same network on both devices).

Sidecar was working fine until a few days ago, no hiccups -- I have no idea what broke it.

Apple, please take care of this asap. We should not have to reboot $4000 worth of hardware to get this to work in this day and age.

To resolve this just go into Settings, General, Reset all settings

Me too! I can only get it to work when they both are connected via cable. As soon as you try a WiFi connection the message of "device timed out" comes up.

I only reset the iPad once. So far it's still working properly. I think AirPlay may still a bit buggy, sometimes my iPad screen doesn't change when it should and I have to disconnect then reconnect.

I am having the same issues i will try sigining out and signing back in, resetting seems like a extreme solution

yes, to completely solve the problem is reset both your mac and iPad.

but, i decide to use ubuntu and leave mac os, and iPad.

Having similar issues...

MacBook Pro (15in) 2019 and iPad Pro (12.9in) 2018 does not connect over wifi or direct cable.

Also have a MacBook Pro (13in) and 2018 and iPad Pro(11in) 2018 that connected fine over wireless.

The settings are all the same per the requirements to have the devices connect.