diff --git a/pkg/machine/machine_windows.go b/pkg/machine/machine_windows.go
index 921e1947de..552babc89f 100644
--- a/pkg/machine/machine_windows.go
+++ b/pkg/machine/machine_windows.go
@@ -128,7 +128,7 @@ func LaunchWinProxy(opts WinProxyOpts, noInfo bool) {
 func launchWinProxy(opts WinProxyOpts) (bool, string, error) {
 	machinePipe := env.WithPodmanPrefix(opts.Name)
 	if !PipeNameAvailable(machinePipe, MachineNameWait) {
-		return false, "", fmt.Errorf("could not start api proxy since expected pipe is not available: %s", machinePipe)
+		return false, "", fmt.Errorf("could not start api proxy since expected pipe is not available: %s (an existing proxy process like win-sshproxy or gvproxy may still be running from a previous machine session; try terminating it and retrying)", machinePipe)
 	}
 
 	globalName := PipeNameAvailable(GlobalNamedPipe, GlobalNameWait)
diff --git a/pkg/machine/shim/networking_windows.go b/pkg/machine/shim/networking_windows.go
index 0fec994c79..2359ed4d68 100644
--- a/pkg/machine/shim/networking_windows.go
+++ b/pkg/machine/shim/networking_windows.go
@@ -13,7 +13,7 @@ import (
 func setupMachineSockets(mc *vmconfigs.MachineConfig, _ *define.MachineDirs) ([]string, string, machine.APIForwardingState, error) {
 	machinePipe := env.WithPodmanPrefix(mc.Name)
 	if !machine.PipeNameAvailable(machinePipe, machine.MachineNameWait) {
-		return nil, "", 0, fmt.Errorf("could not start api proxy since expected pipe is not available: %s", machinePipe)
+		return nil, "", 0, fmt.Errorf("could not start api proxy since expected pipe is not available: %s (an existing proxy process like win-sshproxy or gvproxy may still be running from a previous machine session; try terminating it and retrying)", machinePipe)
 	}
 	sockets := []string{machine.NamedPipePrefix + machinePipe}
 	state := machine.MachineLocal