diff --git a/control/controlclient/auto.go b/control/controlclient/auto.go
index 93598d15a..188e8024d 100644
--- a/control/controlclient/auto.go
+++ b/control/controlclient/auto.go
@@ -59,15 +59,17 @@ type Auto struct {
 
 	mu sync.Mutex // mutex guards the following fields
 
-	paused          bool // whether we should stop making HTTP requests
-	unpauseWaiters  []chan struct{}
-	loggedIn        bool       // true if currently logged in
-	loginGoal       *LoginGoal // non-nil if some login activity is desired
-	synced          bool       // true if our netmap is up-to-date
-	inPollNetMap    bool       // true if currently running a PollNetMap
-	inLiteMapUpdate bool       // true if a lite (non-streaming) map request is outstanding
-	inSendStatus    int        // number of sendStatus calls currently in progress
-	state           State
+	paused               bool // whether we should stop making HTTP requests
+	unpauseWaiters       []chan struct{}
+	loggedIn             bool       // true if currently logged in
+	loginGoal            *LoginGoal // non-nil if some login activity is desired
+	synced               bool       // true if our netmap is up-to-date
+	inPollNetMap         bool       // true if currently running a PollNetMap
+	inLiteMapUpdate      bool       // true if a lite (non-streaming) map request is outstanding
+	liteMapUpdateCancel  func()     // cancels a lite map update
+	liteMapUpdateCancels int        // how many times we've canceled a lite map update
+	inSendStatus         int        // number of sendStatus calls currently in progress
+	state                State
 
 	authCtx    context.Context // context used for auth requests
 	mapCtx     context.Context // context used for netmap requests
@@ -168,28 +170,55 @@ func (c *Auto) Start() {
 func (c *Auto) sendNewMapRequest() {
 	c.mu.Lock()
 
-	// If we're not already streaming a netmap, or if we're already stuck
-	// in a lite update, then tear down everything and start a new stream
-	// (which starts by sending a new map request)
-	if !c.inPollNetMap || c.inLiteMapUpdate || !c.loggedIn {
+	// If we're not already streaming a netmap, then tear down everything
+	// and start a new stream (which starts by sending a new map request)
+	if !c.inPollNetMap || !c.loggedIn {
 		c.mu.Unlock()
 		c.cancelMapSafely()
 		return
 	}
 
+	// If we are already in process of doing a LiteMapUpdate, cancel it and
+	// try a new one. If this is the 10th time we have done this
+	// cancelation, tear down everything and start again
+	if c.inLiteMapUpdate {
+		// Always cancel the in-flight lite map update, regardless of
+		// whether we cancel the streaming map request or not.
+		c.liteMapUpdateCancel()
+		c.inLiteMapUpdate = false
+
+		if c.liteMapUpdateCancels > 10 {
+			// Not making progress
+			c.mu.Unlock()
+			c.cancelMapSafely()
+			return
+		}
+
+		// Increment our cancel counter and continue below to start a
+		// new lite update.
+		c.liteMapUpdateCancels++
+	}
+
 	// Otherwise, send a lite update that doesn't keep a
 	// long-running stream response.
 	defer c.mu.Unlock()
 	c.inLiteMapUpdate = true
 	ctx, cancel := context.WithTimeout(c.mapCtx, 10*time.Second)
+	c.liteMapUpdateCancel = cancel
 	go func() {
 		defer cancel()
 		t0 := time.Now()
 		err := c.direct.SendLiteMapUpdate(ctx)
 		d := time.Since(t0).Round(time.Millisecond)
+
 		c.mu.Lock()
 		c.inLiteMapUpdate = false
+		c.liteMapUpdateCancel = nil
+		if err == nil {
+			c.liteMapUpdateCancels = 0
+		}
 		c.mu.Unlock()
+
 		if err == nil {
 			c.logf("[v1] successful lite map update in %v", d)
 			return
@@ -197,10 +226,13 @@ func (c *Auto) sendNewMapRequest() {
 		if ctx.Err() == nil {
 			c.logf("lite map update after %v: %v", d, err)
 		}
-		// Fall back to restarting the long-polling map
-		// request (the old heavy way) if the lite update
-		// failed for any reason.
-		c.cancelMapSafely()
+		if !errors.Is(ctx.Err(), context.Canceled) {
+			// Fall back to restarting the long-polling map
+			// request (the old heavy way) if the lite update
+			// failed for reasons other than the context being
+			// canceled.
+			c.cancelMapSafely()
+		}
 	}()
 }
 
@@ -237,6 +269,12 @@ func (c *Auto) cancelMapSafely() {
 	c.mu.Lock()
 	defer c.mu.Unlock()
 
+	// Always reset our lite map cancels counter if we're canceling
+	// everything, since we're about to restart with a new map update; this
+	// allows future calls to sendNewMapRequest to retry sending lite
+	// updates.
+	c.liteMapUpdateCancels = 0
+
 	c.logf("[v1] cancelMapSafely: synced=%v", c.synced)
 
 	if c.inPollNetMap {