diff --git a/hostinfo/hostinfo.go b/hostinfo/hostinfo.go
index 9ca8418ef..2280c6a5a 100644
--- a/hostinfo/hostinfo.go
+++ b/hostinfo/hostinfo.go
@@ -7,8 +7,10 @@
 
 import (
 	"bufio"
+	"bytes"
 	"io"
 	"os"
+	"os/exec"
 	"runtime"
 	"runtime/debug"
 	"strings"
@@ -434,3 +436,12 @@ func etcAptSourceFileIsDisabled(r io.Reader) bool {
 	}
 	return disabled
 }
+
+// IsSELinuxEnforcing reports whether SELinux is in "Enforcing" mode.
+func IsSELinuxEnforcing() bool {
+	if runtime.GOOS != "linux" {
+		return false
+	}
+	out, _ := exec.Command("getenforce").Output()
+	return string(bytes.TrimSpace(out)) == "Enforcing"
+}
diff --git a/ipn/ipnlocal/local.go b/ipn/ipnlocal/local.go
index efa4088ec..330f2a8c2 100644
--- a/ipn/ipnlocal/local.go
+++ b/ipn/ipnlocal/local.go
@@ -4,7 +4,6 @@
 package ipnlocal
 
 import (
-	"bytes"
 	"context"
 	"encoding/base64"
 	"encoding/json"
@@ -18,7 +17,6 @@
 	"net/netip"
 	"net/url"
 	"os"
-	"os/exec"
 	"os/user"
 	"path/filepath"
 	"runtime"
@@ -2583,7 +2581,7 @@ func (b *LocalBackend) checkSSHPrefsLocked(p *ipn.Prefs) error {
 		if distro.Get() == distro.QNAP && !envknob.UseWIPCode() {
 			return errors.New("The Tailscale SSH server does not run on QNAP.")
 		}
-		checkSELinux()
+		b.updateSELinuxHealthWarning()
 		// otherwise okay
 	case "darwin":
 		// okay only in tailscaled mode for now.
@@ -4705,12 +4703,8 @@ func (b *LocalBackend) sshServerOrInit() (_ SSHServer, err error) {
 
 var warnSSHSELinux = health.NewWarnable()
 
-func checkSELinux() {
-	if runtime.GOOS != "linux" {
-		return
-	}
-	out, _ := exec.Command("getenforce").Output()
-	if string(bytes.TrimSpace(out)) == "Enforcing" {
+func (b *LocalBackend) updateSELinuxHealthWarning() {
+	if hostinfo.IsSELinuxEnforcing() {
 		warnSSHSELinux.Set(errors.New("SELinux is enabled; Tailscale SSH may not work. See https://tailscale.com/s/ssh-selinux"))
 	} else {
 		warnSSHSELinux.Set(nil)
@@ -4722,7 +4716,7 @@ func (b *LocalBackend) handleSSHConn(c net.Conn) (err error) {
 	if err != nil {
 		return err
 	}
-	checkSELinux()
+	b.updateSELinuxHealthWarning()
 	return s.HandleSSHConn(c)
 }
 
diff --git a/ssh/tailssh/incubator.go b/ssh/tailssh/incubator.go
index a0e79011e..4de3e2b88 100644
--- a/ssh/tailssh/incubator.go
+++ b/ssh/tailssh/incubator.go
@@ -34,6 +34,7 @@
 	"golang.org/x/exp/slices"
 	"golang.org/x/sys/unix"
 	"tailscale.com/cmd/tailscaled/childproc"
+	"tailscale.com/hostinfo"
 	"tailscale.com/tempfork/gliderlabs/ssh"
 	"tailscale.com/types/logger"
 	"tailscale.com/version/distro"
@@ -120,10 +121,18 @@ func (ss *sshSession) newIncubatorCommand() (cmd *exec.Cmd) {
 		if isShell {
 			incubatorArgs = append(incubatorArgs, "--shell")
 		}
-		if isShell || runtime.GOOS == "darwin" {
-			// Only the macOS version of the login command supports executing a
-			// command, all other versions only support launching a shell
-			// without taking any arguments.
+		// Only the macOS version of the login command supports executing a
+		// command, all other versions only support launching a shell
+		// without taking any arguments.
+		shouldUseLoginCmd := isShell || runtime.GOOS == "darwin"
+		if hostinfo.IsSELinuxEnforcing() {
+			// If we're running on a SELinux-enabled system, the login
+			// command will be unable to set the correct context for the
+			// shell. Fall back to using the incubator to launch the shell.
+			// See http://github.com/tailscale/tailscale/issues/4908.
+			shouldUseLoginCmd = false
+		}
+		if shouldUseLoginCmd {
 			if lp, err := exec.LookPath("login"); err == nil {
 				incubatorArgs = append(incubatorArgs, "--login-cmd="+lp)
 			}