Sidecar does not connect when vpn enabled

I’m struggling with the same issue. I’m using Cisco AnyConnect VPN. As soon as I’m connected to the VPN side car stops working, the connection will keep on timing out. Soon as I disconnect the VPN side car works fine.

I'm also having the issue with Cisco AnyConnect VPN. I disconnect and it works fine.

As a further data-point:

• I use ProtonVPN, not ExpressVPN.
• Sidecar works fine when the Mac has a VPN running.
• Enabling the VPN on the iPad, though, prevents Sidecar from connecting, and disconnects sidecar if I enable the VPN while a Sidecar session is running.

It'd be nice to see a fix for this, but I'd much prefer portrait-mode support first. :P

In my experience, the sidecar disconnects once I connect using Cisco AnyConnect VPN. It never gave an error message. However, when I connect using the cable, it disconnects and shows..."Unable to Connnect to "iPad"; A miscellaneous error occurred (32002) then the iPad screen goes black.

Carrott1 - worked for me. And then when ExpressVPN updated I had to once again "disable network lock under preferences > general".

Haven't tried cable connection, but the problem is the same on wifi. Suspect the problem lies in the fact that Sidecar is a .prefpane not an application and it cannot be added to the Split Tunnel list.

Unless someone knows how… ?

If utilising VPN, its connectivity (and limitations thereof) will be greatly influenced by the VPN implementation - which will vary greatly.

If using a VPN App to control connectivity, in lieu of native iPadOS/iOS configuration options, you have little control over the VPN as to whether split-tunnelling is either enabled or inhibited - or the networking protocols/interfaces that are permitted.

Without attempting to delve into deep technicalities of VPNs, networking stacks and connectivity, suffice to say that network connectivity is much more complicated when using a VPN connection. Unless you have total control over the VPN connection (which is very difficult within iPadOS/iOS as very little is exposed via native settings) you are at complete mercy of the VPN App.

In summary, if something (such as Sidecar) works without VPN, but fails with VPN, then your support question must be addressed to your chosen VPN provider.

Without delving into the deep technicalities of how VPNs work, unless “split tunnelling” is enabled and appropriately configured, all VPN client Apps have the capacity to interfere with local network traffic.

Multiple network protocols and ports are utilised to provide Sidecar, Airplay and other functionality - and disruption to any one of the necessary protocols/ports will inhibit this (and potentially other system services).

If VPN software is installed - but is inactive - then local Apple services should operate and route network packets as expected. However, if the VPN software is active - and routing all traffic through the VPN tunnel - then local services (such as AirPlay and Sidecar) are unlikely to be available for the duration of the VPN session.

When VPN Apps are uninstalled, it seems that some fail to correctly restore the local network stack to its “normal” state - and consequently some network connectivity remains unexpectedly disrupted. Reset of the device Network Settings (Settings > General > Reset > Reset Network Settings) should restore nominal network connectivity; in extremis, and full device reset might be necessary.

For SideCar to operate as described, your Mac must be split-tunnelling its network traffic - traffic to your local network network being routed outside of the VPN. By contrast, your iPad VPN-client is evidently routing all network traffic to the VPN tunnel - and as SideCar relies upon the local network to carry traffic between the Mac & iPad, then, it cannot exchange traffic with the Mac - and SideCar breaks.

The “fix” is technically simple - in that the VPN-clients at both ends of the connection must be securely configured to permit split-tunnelling - with local network traffic (or at least, the necessary protocols and client addresses for SideCar clients) remaining outside the VPN tunnel.

Unfortunately, outside of Enterprise configurations/environments where a “profile” is built and installed upon the iDevice, most VPN commercial clients (that can be installed on the iDevice) lack this level of configuration control. Herein lies the fundamental issue; the VPN-client developer must expose these configuration elements to the end-user - and the VPN-client developer is constrained by Apple’s rules concerning Apps.

As such, whilst from a technical perspective the “issue” is easy to resolve, on a practical level it is considerably more difficult.

Can't comment on all VPN configs but sidecar works fine when I'm using my IPSEC VPN connection on my MacBook with or without the USB-C cable plugged into my iPad Pro.

Small issue I'm having on Catalina is the VPN disconnects every 8 minutes - that bug was resolved ages ago but seems to be back.

Have just tried NordVPN and that works fine. Looks like the problem is with ExpressVPN

I have exactly the issue on my Mac with ExpressVPN. Btw AirDrop also not working when VPN is connected.

I wonder is there a official solution from Apple too