diff --git a/internal/vm/libkrun/instance.go b/internal/vm/libkrun/instance.go
index 3814c6b..7ce33e6 100644
--- a/internal/vm/libkrun/instance.go
+++ b/internal/vm/libkrun/instance.go
@@ -246,10 +246,19 @@ func (v *vmInstance) Start(ctx context.Context, opts ...vm.StartOpt) (err error)
 		return fmt.Errorf("failed to get cwd: %w", err)
 	}
 	socketPath := filepath.Join(v.state, "run_vminitd.sock")
+	// Compute the relative socket path to avoid exceeding the max length on macOS.
 	socketPath, err = filepath.Rel(cwd, socketPath)
 	if err != nil {
 		return fmt.Errorf("failed to get relative socket path: %w", err)
 	}
+	// When the socket path exceeds macOS max length, it appears as if the VM
+	// didn't start properly. There's no easy way to figure this out as the
+	// only log is: "Timeout while waiting for VM to start". Thus, return an
+	// error preventively here.
+	if runtime.GOOS == "darwin" && len(socketPath) >= 104 {
+		return fmt.Errorf("socket path is too long: %s", socketPath)
+	}
+
 	if err := v.vmc.AddVSockPort(1025, socketPath); err != nil {
 		return fmt.Errorf("failed to add vsock port: %w", err)
 	}