diff --git a/ipn/ipnserver/server.go b/ipn/ipnserver/server.go
index a69e43067..3d9c9e3d4 100644
--- a/ipn/ipnserver/server.go
+++ b/ipn/ipnserver/server.go
@@ -283,7 +283,18 @@ func (s *Server) blockWhileIdentityInUse(ctx context.Context, actor ipnauth.Acto
 	for inUse() {
 		// Check whenever the connection count drops down to zero.
 		ready, cleanup := s.zeroReqWaiter.add(&s.mu, ctx)
-		<-ready
+		if inUse() {
+			// If the server was in use at the time of the initial check,
+			// but disconnected and was removed from the activeReqs map
+			// by the time we registered a waiter, the ready channel
+			// will never be closed, resulting in a deadlock. To avoid
+			// this, we can check again after registering the waiter.
+			//
+			// This method is planned for complete removal as part of the
+			// multi-user improvements in tailscale/corp#18342,
+			// and this approach should be fine as a temporary solution.
+			<-ready
+		}
 		cleanup()
 		if err := ctx.Err(); err != nil {
 			return err
diff --git a/ipn/ipnserver/server_test.go b/ipn/ipnserver/server_test.go
index e77901c35..e56ae8dab 100644
--- a/ipn/ipnserver/server_test.go
+++ b/ipn/ipnserver/server_test.go
@@ -260,6 +260,52 @@ func TestConcurrentOSUserSwitchingOnWindows(t *testing.T) {
 	}
 }
 
+func TestBlockWhileIdentityInUse(t *testing.T) {
+	enableLogging := false
+	setGOOSForTest(t, "windows")
+
+	ctx := context.Background()
+	server := startDefaultTestIPNServer(t, ctx, enableLogging)
+
+	// connectWaitDisconnectAsUser connects as a user with the specified name
+	// and keeps the IPN bus watcher alive until the context is canceled.
+	// It returns a channel that is closed when done.
+	connectWaitDisconnectAsUser := func(ctx context.Context, name string) <-chan struct{} {
+		client := server.getClientAs(name)
+		watcher, cancelWatcher := client.WatchIPNBus(ctx, 0)
+
+		done := make(chan struct{})
+		go func() {
+			defer cancelWatcher()
+			defer close(done)
+			for {
+				_, err := watcher.Next()
+				if err != nil {
+					// There's either an error or the request has been canceled.
+					break
+				}
+			}
+		}()
+		return done
+	}
+
+	for range 100 {
+		// Connect as UserA, and keep the connection alive
+		// until disconnectUserA is called.
+		userAContext, disconnectUserA := context.WithCancel(ctx)
+		userADone := connectWaitDisconnectAsUser(userAContext, "UserA")
+		disconnectUserA()
+		// Check if userB can connect. Calling it directly increases
+		// the likelihood of triggering a deadlock due to a race condition
+		// in blockWhileIdentityInUse. But the issue also occurs during
+		// the normal execution path when UserB connects to the IPN server
+		// while UserA is disconnecting.
+		userB := server.makeTestUser("UserB", "ClientB")
+		server.blockWhileIdentityInUse(ctx, userB)
+		<-userADone
+	}
+}
+
 func setGOOSForTest(tb testing.TB, goos string) {
 	tb.Helper()
 	envknob.Setenv("TS_DEBUG_FAKE_GOOS", goos)