iOS VPN On Demand with multiple VPNs I have 2 VPNs that I have created on demand profiles for. One is for an OpenVPN server that connects when my iPad is on cellular and disconnects otherwise. The other one automatically connects only on my school's wifi and is an AnyConnect server (only protocol usable at school).

Both of them connect and disconnect fine, but only when their respective VPNs are selected in the VPN settings. However, I have to manually switch them when switching networks--if the cellular VPN was in use, it will disconnect when I connect to school wifi but the school wifi VPN won't connect until I change the current VPN in the settings, which kind of beats the point.

Is there any way to have them switch automatically? Right now I have the settings in two separate profiles, would combining them make a difference? Or am I out of luck?
No, as of iOS 10.3, the VPN won't connect on demand, if it isn't selected in the VPN settings. Obviously, a non-selected VPN setting is meant to be completely inactive, including its on demand configuration. 

I experience the same problem, and am hoping for this feature to be in a coming iOS version, but I am not too positive about it.

However, this answer applies to multiple VPNs of the same type. It seems that if they are of different types, multiple VPNs can be active and even connected at the same time, as described in this question.