diff --git a/ssh/tailssh/incubator.go b/ssh/tailssh/incubator.go
index 1a277d63e..a0e79011e 100644
--- a/ssh/tailssh/incubator.go
+++ b/ssh/tailssh/incubator.go
@@ -452,7 +452,7 @@ func (ss *sshSession) launchProcess() error {
 		return ss.startWithStdPipes()
 	}
 	ss.ptyReq = &ptyReq
-	pty, err := ss.startWithPTY()
+	pty, tty, err := ss.startWithPTY()
 	if err != nil {
 		return err
 	}
@@ -461,10 +461,13 @@ func (ss *sshSession) launchProcess() error {
 	// dup.
 	ptyDup, err := syscall.Dup(int(pty.Fd()))
 	if err != nil {
+		pty.Close()
+		tty.Close()
 		return err
 	}
 	go resizeWindow(ptyDup /* arbitrary fd */, winCh)
 
+	ss.tty = tty
 	ss.stdin = pty
 	ss.stdout = os.NewFile(uintptr(ptyDup), pty.Name())
 	ss.stderr = nil // not available for pty
@@ -544,17 +547,16 @@ func resizeWindow(fd int, winCh <-chan ssh.Window) {
 }
 
 // startWithPTY starts cmd with a pseudo-terminal attached to Stdin, Stdout and Stderr.
-func (ss *sshSession) startWithPTY() (ptyFile *os.File, err error) {
+func (ss *sshSession) startWithPTY() (ptyFile, tty *os.File, err error) {
 	ptyReq := ss.ptyReq
 	cmd := ss.cmd
 	if cmd == nil {
-		return nil, errors.New("nil ss.cmd")
+		return nil, nil, errors.New("nil ss.cmd")
 	}
 	if ptyReq == nil {
-		return nil, errors.New("nil ss.ptyReq")
+		return nil, nil, errors.New("nil ss.ptyReq")
 	}
 
-	var tty *os.File
 	ptyFile, tty, err = pty.Open()
 	if err != nil {
 		err = fmt.Errorf("pty.Open: %w", err)
@@ -568,7 +570,7 @@ func (ss *sshSession) startWithPTY() (ptyFile *os.File, err error) {
 	}()
 	ptyRawConn, err := tty.SyscallConn()
 	if err != nil {
-		return nil, fmt.Errorf("SyscallConn: %w", err)
+		return nil, nil, fmt.Errorf("SyscallConn: %w", err)
 	}
 	var ctlErr error
 	if err := ptyRawConn.Control(func(fd uintptr) {
@@ -615,10 +617,10 @@ func (ss *sshSession) startWithPTY() (ptyFile *os.File, err error) {
 			return
 		}
 	}); err != nil {
-		return nil, fmt.Errorf("ptyRawConn.Control: %w", err)
+		return nil, nil, fmt.Errorf("ptyRawConn.Control: %w", err)
 	}
 	if ctlErr != nil {
-		return nil, fmt.Errorf("ptyRawConn.Control func: %w", ctlErr)
+		return nil, nil, fmt.Errorf("ptyRawConn.Control func: %w", ctlErr)
 	}
 	cmd.SysProcAttr = &syscall.SysProcAttr{
 		Setctty: true,
@@ -642,7 +644,7 @@ func (ss *sshSession) startWithPTY() (ptyFile *os.File, err error) {
 	if err = cmd.Start(); err != nil {
 		return
 	}
-	return ptyFile, nil
+	return ptyFile, tty, nil
 }
 
 // startWithStdPipes starts cmd with os.Pipe for Stdin, Stdout and Stderr.
diff --git a/ssh/tailssh/tailssh.go b/ssh/tailssh/tailssh.go
index e15d4d991..18a2f5a7a 100644
--- a/ssh/tailssh/tailssh.go
+++ b/ssh/tailssh/tailssh.go
@@ -28,6 +28,7 @@
 	"strings"
 	"sync"
 	"sync/atomic"
+	"syscall"
 	"time"
 
 	gossh "github.com/tailscale/golang-x-crypto/ssh"
@@ -811,6 +812,7 @@ type sshSession struct {
 	stdout io.ReadCloser
 	stderr io.Reader // nil for pty sessions
 	ptyReq *ssh.Pty  // non-nil for pty sessions
+	tty    *os.File  // non-nil for pty sessions, must be closed after process exits
 
 	// We use this sync.Once to ensure that we only terminate the process once,
 	// either it exits itself or is terminated
@@ -1087,6 +1089,7 @@ func (ss *sshSession) run() {
 	}
 	go ss.killProcessOnContextDone()
 
+	var processDone atomic.Bool
 	go func() {
 		defer ss.stdin.Close()
 		if _, err := io.Copy(rec.writer("i", ss.stdin), ss); err != nil {
@@ -1104,8 +1107,11 @@ func (ss *sshSession) run() {
 		defer ss.stdout.Close()
 		_, err := io.Copy(rec.writer("o", ss), ss.stdout)
 		if err != nil && !errors.Is(err, io.EOF) {
-			logf("stdout copy: %v", err)
-			ss.cancelCtx(err)
+			isErrBecauseProcessExited := processDone.Load() && errors.Is(err, syscall.EIO)
+			if !isErrBecauseProcessExited {
+				logf("stdout copy: %v, %T", err)
+				ss.cancelCtx(err)
+			}
 		}
 		if openOutputStreams.Add(-1) == 0 {
 			ss.CloseWrite()
@@ -1124,7 +1130,12 @@ func (ss *sshSession) run() {
 		}()
 	}
 
+	if ss.tty != nil {
+		// If running a tty session, close the tty when the session is done.
+		defer ss.tty.Close()
+	}
 	err = ss.cmd.Wait()
+	processDone.Store(true)
 	// This will either make the SSH Termination goroutine be a no-op,
 	// or itself will be a no-op because the process was killed by the
 	// aforementioned goroutine.