DKMS module not available

If the following command does not list any module after you installed wireguard-dkms,:

modprobe wireguard && lsmod | grep wireguard

or if creating a new link returns:

# ip link add dev wg0 type wireguard
RTNETLINK answers: Operation not supported

you probably miss the linux headers.

These headers are available in linux-headers or linux-lts-headers depending of the kernel installed on your system.

After installing the appropriate linux kernel headers,:

apt -y install linux-headers-$(uname -r)

just do:

dpkg-reconfigure wireguard-dkms

Configuration

To dump the WireGuard configuration, use:

wg showconf wg0-server

Connectivity

Running:

tcpdump -i wg0-server

in combination with an ICMP ping:

vagrant@tf-alice:~# ping 10.10.10.52

on both machines might tell you whether your packets are reaching the remote peer or if they're not getting through the tunnel.