diff --git a/os/windows.go b/os/windows.go
index e3a62ee9..95f157ec 100644
--- a/os/windows.go
+++ b/os/windows.go
@@ -177,11 +177,46 @@ func (c Windows) CommandExist(h Host, cmd string) bool {
 	return h.Execf("where /q %s", cmd) == nil
 }
 
-// Reboot executes the reboot command
+// Reboot triggers an immediate forced restart by scheduling a SYSTEM-context
+// one-shot task that runs 'shutdown /r /f /t 5', then immediately triggering
+// and deleting it within the 5-second countdown window.
+//
+// Running via a scheduled task bypasses the filtered Administrator token used
+// by WinRM sessions (e.g. AWS EC2) which lacks SeShutdownPrivilege. Issuing
+// 'shutdown /r' directly in the WinRM session is silently ignored in that
+// context.
+//
+// /sc onstart is used instead of /sc once to avoid schtasks writing a
+// stderr warning about the start time being in the past, which rig treats
+// as an error. The task is deleted immediately after triggering (while the
+// 5-second timer counts down) so it does not re-fire on subsequent startups.
 func (c Windows) Reboot(h Host) error {
-	if err := h.Exec("shutdown /r /t 5"); err != nil {
-		return fmt.Errorf("failed to reboot: %w", err)
+	const taskName = "RigReboot"
+	// Create a SYSTEM-context ONSTART task that runs 'shutdown /r /f /t 5'.
+	// The 5-second delay gives us time to delete the task before the OS
+	// actually executes the reboot, preventing it from firing again on the
+	// next startup.
+	create := fmt.Sprintf(`schtasks /create /tn "%s" /tr "shutdown /r /f /t 5" /sc onstart /f /ru SYSTEM`, taskName)
+	if err := h.Exec(create); err != nil {
+		return fmt.Errorf("failed to create reboot task: %w", err)
 	}
+	run := fmt.Sprintf(`schtasks /run /tn "%s"`, taskName)
+	if err := h.Exec(run); err != nil {
+		// Tolerate connection-level errors; the OS may kill WinRM as it starts
+		// rebooting before the run command returns.
+		errMsg := err.Error()
+		if !strings.Contains(errMsg, "connection") && !strings.Contains(errMsg, "closed") && !strings.Contains(errMsg, "EOF") {
+			return fmt.Errorf("failed to run reboot task: %w", err)
+		}
+	}
+	// Delete the task immediately while the 5-second shutdown timer is still
+	// counting down. This prevents it from re-firing on subsequent startups.
+	del := fmt.Sprintf(`schtasks /delete /tn "%s" /f`, taskName)
+	// Best-effort: ignore delete errors — if the task fires before we can
+	// delete it, the caller is expected to delete it after reconnecting.
+	_ = h.Exec(del)
+	// Allow Windows time to complete shutdown before waitForHost begins polling.
+	time.Sleep(15 * time.Second)
 	return nil
 }
 
diff --git a/winrm.go b/winrm.go
index e7eb3928..8ad58f5e 100644
--- a/winrm.go
+++ b/winrm.go
@@ -197,17 +197,8 @@ type Command struct {
 }
 
 // Wait blocks until the command finishes
-func (c *Command) Wait() (err error) { //nolint:nonamedreturns // needed for panic recovery
-	defer func() {
-		if r := recover(); err == nil && r != nil {
-			if strings.Contains(fmt.Sprint(r), "close of closed channel") {
-				log.Debugf("recovered from a panic in Command.Wait: %v", r)
-			} else {
-				panic(r)
-			}
-		}
-	}()
-
+// Wait blocks until the command finishes
+func (c *Command) Wait() error {
 	defer c.sh.Close()
 	defer c.cmd.Close()
 
@@ -215,9 +206,9 @@ func (c *Command) Wait() (err error) { //nolint:nonamedreturns // needed for pan
 	c.cmd.Wait()
 	log.Debugf("command finished")
 	if c.cmd.ExitCode() != 0 {
-		err = fmt.Errorf("%w: exit code %d", ErrCommandFailed, c.cmd.ExitCode())
+		return fmt.Errorf("%w: exit code %d", ErrCommandFailed, c.cmd.ExitCode())
 	}
-	return err
+	return nil
 }
 
 // Close terminates the command
@@ -319,26 +310,19 @@ func (c *WinRM) Exec(cmd string, opts ...exec.Option) error { //nolint:cyclop
 		}()
 	}
 
+	var errors []string
+
 	wg.Add(1)
 	go func() {
-		// ignore channel close panics
-		defer func() {
-			if r := recover(); r != nil {
-				log.Debugf("recovered from a panic while reading stderr: %v", r)
-			}
-		}()
 		defer wg.Done()
 		if execOpts.Writer == nil {
 			outputScanner := bufio.NewScanner(command.Stdout)
-
 			for outputScanner.Scan() {
 				execOpts.AddOutput(c.String(), outputScanner.Text()+"\n", "")
 			}
-
 			if err := outputScanner.Err(); err != nil {
 				execOpts.LogErrorf("%s: %s", c, err.Error())
 			}
-			command.Stdout.Close()
 		} else {
 			if _, err := io.Copy(execOpts.Writer, command.Stdout); err != nil {
 				execOpts.LogErrorf("%s: failed to stream stdout: %v", c, err)
@@ -346,19 +330,10 @@ func (c *WinRM) Exec(cmd string, opts ...exec.Option) error { //nolint:cyclop
 		}
 	}()
 
-	var errors []string
-
 	wg.Add(1)
 	go func() {
-		// ignore channel close panics
-		defer func() {
-			if r := recover(); r != nil {
-				log.Debugf("recovered from a panic while reading stderr: %v", r)
-			}
-		}()
 		defer wg.Done()
 		outputScanner := bufio.NewScanner(command.Stderr)
-
 		for outputScanner.Scan() {
 			msg := outputScanner.Text()
 			if msg != "" {
@@ -366,11 +341,9 @@ func (c *WinRM) Exec(cmd string, opts ...exec.Option) error { //nolint:cyclop
 				execOpts.LogErrorf("%s: %s", c, msg)
 			}
 		}
-
 		if err := outputScanner.Err(); err != nil {
 			execOpts.LogErrorf("%s: %s", c, err.Error())
 		}
-		command.Stderr.Close()
 	}()
 
 	wg.Wait()