diff --git a/docs/wsl1.md b/docs/wsl1.md
new file mode 100644
index 0000000000000..1a29ed015a247
--- /dev/null
+++ b/docs/wsl1.md
@@ -0,0 +1,49 @@
+# Running Tailscale on WSL1
+
+WSL1 (kernel `4.4.0-*-Microsoft`) emulates Linux syscalls on the NT kernel
+and needs two deviations from a stock Linux deployment of Tailscale.
+
+## tailscaled must be built with cgo
+
+Symptom of a non-cgo build: every Tailscale SSH command execution
+(`ssh host cmd`, scp, sftp) hangs, and a `tailscaled be-child ssh ...`
+process spins at 100% CPU until the client disconnects. Interactive login
+shells still work, because they go through `/bin/login`, which changes
+users on its own.
+
+Cause: WSL1's `tgkill` is missing real Linux's same-thread-group exception
+in its signal permission check. The SSH incubator drops privileges with
+Go's `syscall.Setuid`, which without cgo applies the syscall on the calling
+thread first and then signals every other OS thread (`AllThreadsSyscall`).
+After the first thread transitions root -> user, WSL1 rejects the signals
+to the remaining root threads with EPERM; the Go runtime ignores the
+error and spin-waits forever. glibc's setuid signals sibling threads
+*before* transitioning, so a cgo build — which dispatches `Setuid` to
+glibc — works.
+
+Build both binaries release-style, with only cgo flipped on:
+
+    TS_USE_TOOLCHAIN=1 CGO_ENABLED=1 ./build_dist.sh tailscale.com/cmd/tailscaled
+    TS_USE_TOOLCHAIN=1 CGO_ENABLED=1 ./build_dist.sh tailscale.com/cmd/tailscale
+
+Notes:
+
+- The resulting binaries are dynamically linked against glibc, so build
+  them on (or for) the machine that runs them.
+- cgo needs the Linux UAPI headers (`/usr/include/linux`); on Slackware
+  install the `kernel-headers` package first.
+- WSL1 has no TUN device; run tailscaled with
+  `--tun=userspace-networking`.
+
+## TS_OS_SPOOF_WINDOWS
+
+`version.OS()` reports `windows` on Linux only when
+`TS_OS_SPOOF_WINDOWS=1` is set in tailscaled's environment. This exists
+for the dual-boot state-sharing setup, where a Linux install reuses the
+state written by a Windows Tailscale and should keep presenting itself as
+that Windows node.
+
+Do not set it on an established Linux node: the coordination server flags
+the OS change ("node OS changed since last connection, was node state
+copied between devices?") and serves the node an empty peer list and an
+empty Tailscale SSH policy, which disables SSH access entirely.
diff --git a/version/prop.go b/version/prop.go
index 9cc6d08bfcc9f..fd5a58bbbb54a 100644
--- a/version/prop.go
+++ b/version/prop.go
@@ -54,12 +54,23 @@ func OS() string {
 	if runtime.GOOS == "darwin" {
 		return "macOS"
 	}
-	if runtime.GOOS == "linux" {
+	if runtime.GOOS == "linux" && spoofWindowsOS() {
 		return "windows"
 	}
 	return runtime.GOOS
 }
 
+// spoofWindowsOS reports whether TS_OS_SPOOF_WINDOWS is set to a true value,
+// making a Linux node report "windows" for dual-boot state sharing with a
+// Windows Tailscale install. It must be opt-in per machine: an established
+// Linux node that flips its reported OS is flagged by the coordination server
+// ("node OS changed since last connection") and receives an empty peer list
+// and an empty SSH policy.
+var spoofWindowsOS = sync.OnceValue(func() bool {
+	v, _ := strconv.ParseBool(os.Getenv("TS_OS_SPOOF_WINDOWS"))
+	return v
+})
+
 // IsMacGUIVariant reports whether runtime.GOOS=="darwin" and this one of the
 // two GUI variants (that is, not tailscaled-on-macOS).
 // This predicate should not be used to determine sandboxing properties. It's