diff --git a/ipn/ipnlocal/local.go b/ipn/ipnlocal/local.go
index ea5af0897..23d525a69 100644
--- a/ipn/ipnlocal/local.go
+++ b/ipn/ipnlocal/local.go
@@ -144,6 +144,29 @@ func RegisterNewSSHServer(fn newSSHServerFunc) {
 	newSSHServer = fn
 }
 
+// listenSSHFunc, if non-nil, is the implementation of ListenSSH provided by the
+// ssh/tailssh package via RegisterListenSSH.
+var listenSSHFunc func(net.Listener, *LocalBackend, logger.Logf) (net.Listener, error)
+
+// RegisterListenSSH lets the conditionally linked ssh/tailssh package register
+// an implementation of ListenSSH for use by tsnet.
+func RegisterListenSSH(fn func(net.Listener, *LocalBackend, logger.Logf) (net.Listener, error)) {
+	listenSSHFunc = fn
+}
+
+// ListenSSH wraps the given listener with an SSH server that authenticates
+// connections using Tailscale peer identity. The returned listener's Accept
+// yields net.Conn values that are *tailssh.Session.
+//
+// If the ssh/tailssh package has not been linked (e.g. via
+// _ "tailscale.com/feature/ssh"), ListenSSH returns an error.
+func (b *LocalBackend) ListenSSH(ln net.Listener, logf logger.Logf) (net.Listener, error) {
+	if listenSSHFunc == nil {
+		return nil, errors.New("SSH support not available; import _ \"tailscale.com/feature/ssh\"")
+	}
+	return listenSSHFunc(ln, b, logf)
+}
+
 // watchSession represents a WatchNotifications channel,
 // an [ipnauth.Actor] that owns it (e.g., a connected GUI/CLI),
 // and sessionID as required to close targeted buses.
diff --git a/ssh/tailssh/listen.go b/ssh/tailssh/listen.go
new file mode 100644
index 000000000..04fa14d87
--- /dev/null
+++ b/ssh/tailssh/listen.go
@@ -0,0 +1,136 @@
+// Copyright (c) Tailscale Inc & contributors
+// SPDX-License-Identifier: BSD-3-Clause
+
+//go:build (linux && !android) || (darwin && !ios) || freebsd || openbsd || plan9
+
+package tailssh
+
+import (
+	"errors"
+	"net"
+	"net/netip"
+	"sync"
+
+	"tailscale.com/ipn/ipnlocal"
+	"tailscale.com/tempfork/gliderlabs/ssh"
+	"tailscale.com/types/logger"
+)
+
+func init() {
+	ipnlocal.RegisterListenSSH(listenSSH)
+}
+
+// listenSSH wraps rawLn with an SSH server that resolves Tailscale peer
+// identity for each connection. The returned listener's Accept yields
+// *Session values (as net.Conn).
+func listenSSH(rawLn net.Listener, lb *ipnlocal.LocalBackend, logf logger.Logf) (net.Listener, error) {
+	hostKeys, err := getHostKeys(lb.TailscaleVarRoot(), logf)
+	if err != nil {
+		return nil, err
+	}
+	signers := make([]ssh.Signer, len(hostKeys))
+	for i, k := range hostKeys {
+		signers[i] = k
+	}
+
+	sl := &sshListener{
+		rawLn:    rawLn,
+		sessions: make(chan net.Conn, 16),
+		done:     make(chan struct{}),
+	}
+
+	sshSrv := &ssh.Server{
+		HostSigners: signers,
+		Handler: func(sess ssh.Session) {
+			srcAddr := sess.RemoteAddr().String()
+			ipp, err := netip.ParseAddrPort(srcAddr)
+			if err != nil {
+				logf("listenSSH: bad remote addr %q: %v", srcAddr, err)
+				sess.Exit(1)
+				return
+			}
+			node, userProfile, ok := lb.WhoIs("tcp", ipp)
+			if !ok {
+				logf("listenSSH: WhoIs failed for %v", srcAddr)
+				sess.Exit(1)
+				return
+			}
+
+			done := make(chan struct{})
+			s := newSession(sess, PeerIdentity{
+				Node:        node,
+				UserProfile: userProfile,
+			}, done)
+
+			// Send the session to the listener. If the listener is
+			// closed, drop the session.
+			select {
+			case sl.sessions <- s:
+			case <-sl.done:
+				sess.Exit(1)
+				return
+			}
+
+			// Block until the consumer is done with the session.
+			select {
+			case <-done:
+			case <-sess.Context().Done():
+			case <-sl.done:
+			}
+		},
+	}
+
+	go func() {
+		if err := sshSrv.Serve(rawLn); err != nil {
+			// Serve returns when the listener is closed. Only log
+			// unexpected errors.
+			select {
+			case <-sl.done:
+			default:
+				logf("listenSSH: Serve error: %v", err)
+			}
+		}
+		sl.Close()
+	}()
+
+	return sl, nil
+}
+
+// sshListener is a net.Listener that yields *Session values from its Accept
+// method. It wraps a raw TCP listener with an SSH server.
+type sshListener struct {
+	rawLn     net.Listener
+	sessions  chan net.Conn
+	done      chan struct{}
+	closeOnce sync.Once
+}
+
+// Accept returns the next SSH session as a net.Conn. The returned value can
+// be type-asserted to *Session.
+func (l *sshListener) Accept() (net.Conn, error) {
+	select {
+	case s, ok := <-l.sessions:
+		if !ok {
+			return nil, errors.New("listener closed")
+		}
+		return s, nil
+	case <-l.done:
+		return nil, errors.New("listener closed")
+	}
+}
+
+// Close closes the underlying raw listener and signals all pending sessions
+// to terminate.
+func (l *sshListener) Close() error {
+	var err error
+	l.closeOnce.Do(func() {
+		close(l.done)
+		err = l.rawLn.Close()
+	})
+	return err
+}
+
+// Addr returns the address of the underlying raw listener.
+func (l *sshListener) Addr() net.Addr {
+	return l.rawLn.Addr()
+}
diff --git a/ssh/tailssh/session.go b/ssh/tailssh/session.go
new file mode 100644
index 000000000..d88df1455
--- /dev/null
+++ b/ssh/tailssh/session.go
@@ -0,0 +1,210 @@
+// Copyright (c) Tailscale Inc & contributors
+// SPDX-License-Identifier: BSD-3-Clause
+
+//go:build (linux && !android) || (darwin && !ios) || freebsd || openbsd || plan9
+
+package tailssh
+
+import (
+	"context"
+	"errors"
+	"io"
+	"net"
+	"time"
+
+	"tailscale.com/tailcfg"
+	"tailscale.com/tempfork/gliderlabs/ssh"
+)
+
+var errNoDeadline = errors.New("tailssh.Session: deadlines not supported")
+
+// Signal represents an SSH signal (e.g. "INT", "TERM").
+type Signal = ssh.Signal
+
+// Pty represents a PTY request and configuration.
+type Pty struct {
+	// Term is the TERM environment variable value.
+	Term string
+
+	// Window is the initial window size.
+	Window Window
+
+	// Modes are the RFC 4254 terminal modes as opcode/value pairs.
+	Modes map[uint8]uint32
+}
+
+// Window represents the size of a PTY window.
+type Window struct {
+	Width        int
+	Height       int
+	WidthPixels  int
+	HeightPixels int
+}
+
+// PeerIdentity contains the Tailscale identity of the connecting SSH peer.
+type PeerIdentity struct {
+	Node        tailcfg.NodeView
+	UserProfile tailcfg.UserProfile
+}
+
+// Session wraps a gliderlabs ssh.Session with Tailscale peer identity
+// information. It implements net.Conn so callers that only need Read/Write/Close
+// can use it directly. Callers that need SSH-specific functionality can
+// type-assert from the net.Conn returned by the listener's Accept.
+type Session struct {
+	// sess is the underlying gliderlabs SSH session.
+	sess ssh.Session
+
+	// peer is the Tailscale identity of the remote peer.
+	peer PeerIdentity
+
+	// done is closed when the session handler should return,
+	// unblocking the gliderlabs handler goroutine.
+	done chan struct{}
+}
+
+// newSession creates a new Session wrapping the given gliderlabs session and
+// peer identity. The done channel is closed by the session consumer to signal
+// that the handler goroutine may return.
+func newSession(sess ssh.Session, peer PeerIdentity, done chan struct{}) *Session {
+	return &Session{
+		sess: sess,
+		peer: peer,
+		done: done,
+	}
+}
+
+// Read reads from the SSH channel (stdin from the client).
+func (s *Session) Read(p []byte) (int, error) {
+	return s.sess.Read(p)
+}
+
+// Write writes to the SSH channel (stdout to the client).
+func (s *Session) Write(p []byte) (int, error) {
+	return s.sess.Write(p)
+}
+
+// Close signals the session handler to return and closes the underlying channel.
+func (s *Session) Close() error {
+	select {
+	case <-s.done:
+	default:
+		close(s.done)
+	}
+	return nil
+}
+
+// RemoteAddr returns the net.Addr of the client side of the connection.
+func (s *Session) RemoteAddr() net.Addr {
+	return s.sess.RemoteAddr()
+}
+
+// LocalAddr returns the net.Addr of the server side of the connection.
+func (s *Session) LocalAddr() net.Addr {
+	return s.sess.LocalAddr()
+}
+
+// SetDeadline is not supported and returns an error.
+func (s *Session) SetDeadline(t time.Time) error {
+	return errNoDeadline
+}
+
+// SetReadDeadline is not supported and returns an error.
+func (s *Session) SetReadDeadline(t time.Time) error {
+	return errNoDeadline
+}
+
+// SetWriteDeadline is not supported and returns an error.
+func (s *Session) SetWriteDeadline(t time.Time) error {
+	return errNoDeadline
+}
+
+// User returns the SSH username.
+func (s *Session) User() string {
+	return s.sess.User()
+}
+
+// PeerIdentity returns the Tailscale identity of the remote peer.
+func (s *Session) PeerIdentity() PeerIdentity {
+	return s.peer
+}
+
+// Environ returns a copy of the environment variables set by the client.
+func (s *Session) Environ() []string {
+	return s.sess.Environ()
+}
+
+// RawCommand returns the exact command string provided by the client.
+func (s *Session) RawCommand() string {
+	return s.sess.RawCommand()
+}
+
+// Subsystem returns the subsystem requested by the client.
+func (s *Session) Subsystem() string {
+	return s.sess.Subsystem()
+}
+
+// Pty returns PTY information, a channel of window size changes, and whether
+// a PTY was requested. The returned types use this package's Pty and Window
+// types rather than the internal gliderlabs types.
+func (s *Session) Pty() (Pty, <-chan Window, bool) {
+	gPty, gWinCh, ok := s.sess.Pty()
+	if !ok {
+		return Pty{}, nil, false
+	}
+	p := Pty{
+		Term: gPty.Term,
+		Window: Window{
+			Width:        gPty.Window.Width,
+			Height:       gPty.Window.Height,
+			WidthPixels:  gPty.Window.WidthPixels,
+			HeightPixels: gPty.Window.HeightPixels,
+		},
+	}
+	if gPty.Modes != nil {
+		p.Modes = make(map[uint8]uint32, len(gPty.Modes))
+		for k, v := range gPty.Modes {
+			p.Modes[k] = v
+		}
+	}
+
+	// Convert the gliderlabs Window channel to our Window type.
+	winCh := make(chan Window, 1)
+	go func() {
+		defer close(winCh)
+		for gw := range gWinCh {
+			winCh <- Window{
+				Width:        gw.Width,
+				Height:       gw.Height,
+				WidthPixels:  gw.WidthPixels,
+				HeightPixels: gw.HeightPixels,
+			}
+		}
+	}()
+
+	return p, winCh, true
+}
+
+// Signals registers a channel to receive signals from the client.
+// Pass nil to unregister.
+func (s *Session) Signals(c chan<- Signal) {
+	s.sess.Signals(c)
+}
+
+// Exit sends an exit status to the client and closes the session.
+func (s *Session) Exit(code int) error {
+	err := s.sess.Exit(code)
+	s.Close()
+	return err
+}
+
+// Stderr returns an io.Writer for the SSH stderr channel.
+func (s *Session) Stderr() io.Writer {
+	return s.sess.Stderr()
+}
+
+// Context returns the session's context, which is canceled when the client
+// disconnects.
+func (s *Session) Context() context.Context {
+	return s.sess.Context()
+}
diff --git a/tsnet/example/ssh-game/ssh-game.go b/tsnet/example/ssh-game/ssh-game.go
new file mode 100644
index 000000000..a1b07e50c
--- /dev/null
+++ b/tsnet/example/ssh-game/ssh-game.go
@@ -0,0 +1,91 @@
+// Copyright (c) Tailscale Inc & contributors
+// SPDX-License-Identifier: BSD-3-Clause
+
+// The ssh-game server demonstrates how to use tsnet's ListenSSH to build
+// a custom SSH application. It runs a simple "guess the number" game.
+//
+// Usage:
+//
+//	go run ./tsnet/example/ssh-game
+//
+// Then from another Tailscale node:
+//
+//	ssh -p 2222 <hostname>
+package main
+
+import (
+	"bufio"
+	"fmt"
+	"log"
+	"math/rand/v2"
+	"net"
+	"strings"
+
+	_ "tailscale.com/feature/ssh"
+	"tailscale.com/ssh/tailssh"
+	"tailscale.com/tsnet"
+)
+
+func main() {
+	s := &tsnet.Server{
+		Hostname: "ssh-game",
+	}
+	defer s.Close()
+
+	ln, err := s.ListenSSH(":2222")
+	if err != nil {
+		log.Fatal(err)
+	}
+	defer ln.Close()
+	log.Println("Listening on :2222")
+
+	for {
+		conn, err := ln.Accept()
+		if err != nil {
+			log.Fatal(err)
+		}
+		go handleGame(conn)
+	}
+}
+
+func handleGame(c net.Conn) {
+	sess, ok := c.(*tailssh.Session)
+	if !ok {
+		fmt.Fprintf(c, "unexpected connection type\n")
+		c.Close()
+		return
+	}
+	defer sess.Exit(0)
+
+	peer := sess.PeerIdentity()
+	target := rand.IntN(100) + 1
+	scanner := bufio.NewScanner(sess)
+
+	fmt.Fprintf(sess, "Welcome, %s from %s!\r\n",
+		peer.UserProfile.LoginName,
+		peer.Node.ComputedName())
+	fmt.Fprintf(sess, "I'm thinking of a number between 1 and 100.\r\n")
+	fmt.Fprintf(sess, "Can you guess it?\r\n\r\n")
+
+	for attempts := 1; ; attempts++ {
+		fmt.Fprintf(sess, "Your guess: ")
+		if !scanner.Scan() {
+			return
+		}
+		line := strings.TrimSpace(scanner.Text())
+		var guess int
+		if _, err := fmt.Sscanf(line, "%d", &guess); err != nil {
+			fmt.Fprintf(sess, "Please enter a number.\r\n")
+			continue
+		}
+		switch {
+		case guess < target:
+			fmt.Fprintf(sess, "Higher!\r\n")
+		case guess > target:
+			fmt.Fprintf(sess, "Lower!\r\n")
+		default:
+			fmt.Fprintf(sess, "Correct! You got it in %d attempts.\r\n", attempts)
+			return
+		}
+	}
+}
diff --git a/tsnet/tsnet.go b/tsnet/tsnet.go
index 4a116cf34..57cd5a004 100644
--- a/tsnet/tsnet.go
+++ b/tsnet/tsnet.go
@@ -1074,6 +1074,33 @@ func (s *Server) Listen(network, addr string) (net.Listener, error) {
 	return s.listen(network, addr, listenOnTailnet)
 }
 
+// ListenSSH listens on the Tailscale network for SSH connections at the given
+// addr (e.g. ":2222"). The returned listener's Accept method yields net.Conn
+// values that are actually *tailssh.Session, providing access to the
+// connecting peer's Tailscale identity, PTY information, signals, and more.
+//
+// Basic applications can use the returned connections as plain net.Conn
+// (Read/Write/Close). Applications that need richer SSH semantics should
+// type-assert to *tailssh.Session.
+//
+// SSH support must be linked into the binary by importing
+// _ "tailscale.com/feature/ssh". Without that import, ListenSSH returns an
+// error.
+//
+// If s has not been started yet, it will be started.
+func (s *Server) ListenSSH(addr string) (net.Listener, error) {
+	rawLn, err := s.Listen("tcp", addr)
+	if err != nil {
+		return nil, err
+	}
+	sshLn, err := s.lb.ListenSSH(rawLn, s.logf)
+	if err != nil {
+		rawLn.Close()
+		return nil, err
+	}
+	return sshLn, nil
+}
+
 // ListenPacket announces on the Tailscale network.
 //
 // The network must be "udp", "udp4" or "udp6". The addr must be of the form