diff --git a/pkg/machine/hyperv/machine.go b/pkg/machine/hyperv/machine.go
index d93febe3aa..473676a40d 100644
--- a/pkg/machine/hyperv/machine.go
+++ b/pkg/machine/hyperv/machine.go
@@ -178,6 +178,7 @@ func (m *HyperVMachine) Init(opts machine.InitOptions) (bool, error) {
 	// VSOCK-CONNECT:2 <- shortcut to connect to the hostvm
 	ready := `[Unit]
 After=remove-moby.service sshd.socket sshd.service
+After=systemd-user-sessions.service
 OnFailure=emergency.target
 OnFailureJobMode=isolate
 [Service]
diff --git a/pkg/machine/qemu/machine.go b/pkg/machine/qemu/machine.go
index e2d9c91e79..783f5cd368 100644
--- a/pkg/machine/qemu/machine.go
+++ b/pkg/machine/qemu/machine.go
@@ -334,6 +334,7 @@ func (v *MachineVM) Init(opts machine.InitOptions) (bool, error) {
 	ready := `[Unit]
 Requires=dev-virtio\\x2dports-%s.device
 After=remove-moby.service sshd.socket sshd.service
+After=systemd-user-sessions.service
 OnFailure=emergency.target
 OnFailureJobMode=isolate
 [Service]