diff --git a/client/ssh/client.go b/client/ssh/client.go
index 7c0e90fbd..2775c8304 100644
--- a/client/ssh/client.go
+++ b/client/ssh/client.go
@@ -81,7 +81,8 @@ func (c *Client) handleSessionError(err error) error {
 	}
 
 	var e *ssh.ExitError
-	if !errors.As(err, &e) {
+	var em *ssh.ExitMissingError
+	if !errors.As(err, &e) && !errors.As(err, &em) {
 		// Only return actual errors (not exit status errors)
 		return fmt.Errorf("session wait: %w", err)
 	}
@@ -89,6 +90,7 @@ func (c *Client) handleSessionError(err error) error {
 	// SSH should behave like regular command execution:
 	// Non-zero exit codes are normal and should not be treated as errors
 	// The command ran successfully, it just returned a non-zero exit code
+	// ExitMissingError is also normal - session was torn down cleanly
 	return nil
 }
 
@@ -116,12 +118,14 @@ func (c *Client) ExecuteCommand(ctx context.Context, command string) ([]byte, er
 	output, err := session.CombinedOutput(command)
 	if err != nil {
 		var e *ssh.ExitError
-		if !errors.As(err, &e) {
+		var em *ssh.ExitMissingError
+		if !errors.As(err, &e) && !errors.As(err, &em) {
 			// Only return actual errors (not exit status errors)
 			return output, fmt.Errorf("execute command: %w", err)
 		}
 		// SSH should behave like regular command execution:
 		// Non-zero exit codes are normal and should not be treated as errors
+		// ExitMissingError is also normal - session was torn down cleanly
 		// Return the output even for non-zero exit codes
 	}
 
@@ -210,10 +214,14 @@ func (c *Client) handleCommandError(err error) error {
 	}
 
 	var e *ssh.ExitError
-	if !errors.As(err, &e) {
+	var em *ssh.ExitMissingError
+	if !errors.As(err, &e) && !errors.As(err, &em) {
 		return fmt.Errorf("execute command: %w", err)
 	}
 
+	// SSH should behave like regular command execution:
+	// Non-zero exit codes are normal and should not be treated as errors
+	// ExitMissingError is also normal - session was torn down cleanly
 	return nil
 }
 
diff --git a/client/ssh/client_test.go b/client/ssh/client_test.go
index dd8642cf4..bd5e4c38c 100644
--- a/client/ssh/client_test.go
+++ b/client/ssh/client_test.go
@@ -613,7 +613,7 @@ func TestSSHClient_PipedCommand(t *testing.T) {
 	// Test with piped commands that don't require PTY
 	var pipeCmd string
 	if runtime.GOOS == "windows" {
-		pipeCmd = "echo hello world | findstr hello"
+		pipeCmd = "echo hello world | Select-String hello"
 	} else {
 		pipeCmd = "echo 'hello world' | grep hello"
 	}
@@ -1112,9 +1112,9 @@ func TestBehaviorRegression(t *testing.T) {
 				command string
 			}{
 				{"simple echo", "echo test"},
-				{"current directory", "cd"},
-				{"list files", "dir"},
-				{"system info", "systeminfo | findstr /B /C:\"OS Name\""},
+				{"current directory", "Get-Location"},
+				{"list files", "Get-ChildItem"},
+				{"system info", "$PSVersionTable.PSVersion"},
 			}
 		} else {
 			testCases = []struct {
@@ -1231,9 +1231,9 @@ func TestSSHClient_NonZeroExitCodes(t *testing.T) {
 			name    string
 			command string
 		}{
-			{"findstr no match", "echo hello | findstr notfound"},
-			{"exit 1 command", "cmd /c exit 1"},
-			{"dir nonexistent", "dir C:\\nonexistent\\path"},
+			{"select-string no match", "echo hello | Select-String notfound"},
+			{"exit 1 command", "throw \"exit with code 1\""},
+			{"get-childitem nonexistent", "Get-ChildItem C:\\nonexistent\\path"},
 		}
 	} else {
 		testCases = []struct {