diff --git a/CHANGELOG.md b/CHANGELOG.md
index c854a559..4a02e4b6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,6 +8,7 @@ and this project adheres to [Semantic Versioning](http://semver.org/spec/v2.0.0.
 - cleaned up shutdown logic for outbound sender [#205](https://github.com/xmidt-org/caduceus/pull/205)
 - added resetting queue depth and current workers gauges to outbound sender [#205](https://github.com/xmidt-org/caduceus/pull/205)
 - removed queueEmpty variable from outbound sender [#209](https://github.com/xmidt-org/caduceus/pull/209)
+- fixed outbound sender's long running dispatcher() goroutine to not exit when a cutoff occurs [#210](https://github.com/xmidt-org/caduceus/pull/210)
 
 ## [v0.2.7]
 - pared down logging, especially debugging logs [#196](https://github.com/xmidt-org/caduceus/pull/196)
diff --git a/outboundSender.go b/outboundSender.go
index 2062fa3d..fb08a23d 100644
--- a/outboundSender.go
+++ b/outboundSender.go
@@ -440,6 +440,10 @@ func (obs *CaduceusOutboundSender) isValidTimeWindow(now, dropUntil, deliverUnti
 	return true
 }
 
+// Empty is called on cutoff or shutdown and swaps out the current queue for
+// a fresh one, counting any current messages in the queue as dropped.
+// It should never close a queue, as a queue not referenced anywhere will be
+// cleaned up by the garbage collector without needing to be closed.
 func (obs *CaduceusOutboundSender) Empty(droppedCounter metrics.Counter) {
 	droppedMsgs := obs.queue.Load().(chan *wrp.Message)
 	obs.queue.Store(make(chan *wrp.Message, obs.queueSize))
@@ -459,9 +463,31 @@ func (obs *CaduceusOutboundSender) dispatcher() {
 
 Loop:
 	for {
+		// Always pull a new queue in case we have been cutoff or are shutting
+		// down.
 		msgQueue := obs.queue.Load().(chan *wrp.Message)
 		select {
+		// The dispatcher cannot get stuck blocking here forever (caused by an
+		// empty queue that is replaced and then Queue() starts adding to the
+		// new queue) because:
+		// 	- queue is only replaced on cutoff and shutdown
+		//  - on cutoff, the first queue is always full so we will definitely
+		//    get a message, drop it because we're cut off, then get the new
+		//    queue and block until the cut off ends and Queue() starts queueing
+		//    messages again.
+		//  - on graceful shutdown, the queue is closed and then the dispatcher
+		//    will send all messages, then break the loop, gather workers, and
+		//    exit.
+		//  - on non graceful shutdown, the queue is closed and then replaced
+		//    with a new, empty queue that is also closed.
+		//      - If the first queue is empty, we immediately break the loop,
+		//        gather workers, and exit.
+		//      - If the first queue has messages, we drop a message as expired
+		//        pull in the new queue which is empty and closed, break the
+		//        loop, gather workers, and exit.
 		case msg, ok = <-msgQueue:
+			// This is only true when a queue is empty and closed, which for us
+			// only happens on Shutdown().
 			if !ok {
 				break Loop
 			}
@@ -469,6 +495,8 @@ Loop:
 			obs.mutex.RLock()
 			urls = obs.urls
 			// Move to the next URL to try 1st the next time.
+			// This is okay because we run a single dispatcher and it's the
+			// only one updating this field.
 			obs.urls = obs.urls.Next()
 			deliverUntil := obs.deliverUntil
 			dropUntil := obs.dropUntil
@@ -480,7 +508,7 @@ Loop:
 
 			if now.Before(dropUntil) {
 				obs.droppedCutoffCounter.Add(1.0)
-				break Loop
+				continue
 			}
 			if now.After(deliverUntil) {
 				obs.droppedExpiredCounter.Add(1.0)
@@ -609,7 +637,9 @@ func (obs *CaduceusOutboundSender) send(urls *ring.Ring, secret, acceptType stri
 	obs.deliveryCounter.With("url", obs.id, "code", code, "event", event).Add(1.0)
 }
 
-// queueOverflow handles the logic of what to do when a queue overflows
+// queueOverflow handles the logic of what to do when a queue overflows:
+// cutting off the webhook for a time and sending a cut off notification
+// to the failure URL.
 func (obs *CaduceusOutboundSender) queueOverflow() {
 	obs.mutex.Lock()
 	if time.Now().Before(obs.dropUntil) {
@@ -629,6 +659,8 @@ func (obs *CaduceusOutboundSender) queueOverflow() {
 
 	obs.cutOffCounter.Add(1.0)
 
+	// We empty the queue but don't close the channel, because we're not
+	// shutting down.
 	obs.Empty(obs.droppedCutoffCounter)
 
 	msg, err := json.Marshal(failureMsg)