diff --git a/fleetspeak/src/client/client.go b/fleetspeak/src/client/client.go
index b3f94adc..ac307350 100644
--- a/fleetspeak/src/client/client.go
+++ b/fleetspeak/src/client/client.go
@@ -74,8 +74,9 @@ type Client struct {
 	outHigh   chan service.AckMessage
 	outMedium chan service.AckMessage
 	outLow    chan service.AckMessage
-	// used to wait until the retry loop goroutines are done
+	// used to wait until the retry and sort loop goroutines are done
 	retryLoopsDone sync.WaitGroup
+	sortLoopDone   sync.WaitGroup
 
 	acks    chan common.MessageID
 	errs    chan *fspb.MessageErrorData
@@ -149,7 +150,11 @@ func New(cfg config.Configuration, cmps Components) (*Client, error) {
 	if f == nil {
 		f = flow.NewFilter()
 	}
-	go message.SortLoop(ret.outUnsorted, ret.outbox, f)
+	ret.sortLoopDone.Add(1)
+	go func() {
+		message.SortLoop(ret.outUnsorted, ret.outbox, f)
+		ret.sortLoopDone.Done()
+	}()
 
 	ssd := &serviceData{
 		config: ret.sc,
@@ -258,33 +263,49 @@ func (c *Client) ProcessMessage(ctx context.Context, am service.AckMessage) (err
 
 // Stop shuts the client down gracefully. This includes stopping all communicators and services.
 func (c *Client) Stop() {
+	log.Info("Stopping client...")
 	if c.com != nil {
 		c.com.Stop()
 	}
 	c.sc.Stop()
 	c.config.Stop()
-	close(c.outLow)
-	close(c.outMedium)
-	close(c.outHigh)
+	log.Info("Components have been stopped.")
+
 	// From here, shutdown is a little subtle:
 	//
-	// 1) At this point, the communicator is off, so nothing else should be
-	//    draining outbox. We do this ourselves and Ack everything so that the
-	//    RetryLoops are guaranteed to terminate.
+	// - At this point, the communicator is off, so nothing else should be
+	//   draining outbox. We do this ourselves and Ack everything so that the
+	//   RetryLoops are guaranteed to terminate.
 	//
-	// 2) The fake Acks in 1) are safe because the config manager is stopped.
-	//    This means that client services are shut down and the Acks will not be
-	//    reported outside of this process.
+	// - The fake Acks in 1) are safe because the config manager is stopped.
+	//   This means that client services are shut down and the Acks will not be
+	//   reported outside of this process.
+
+	close(c.outLow)
+	close(c.outMedium)
+	close(c.outHigh)
+	c.retryLoopsDone.Wait()
+	log.Info("Retry loops have terminated.")
+
+	// - Now, no more messages enter outUnsorted.
 	//
-	// 3) Then we close outUnsorted so that the SortLoop terminates.
-	for {
-		select {
-		case m := <-c.outbox:
-			m.Ack()
-		default:
-			c.retryLoopsDone.Wait()
-			close(c.outUnsorted)
-			return
+	// - We close outUnsorted and drain outbox, to make sure no messages are lost.
+	//   Once these two things are complete, SortLoop will return, and the client
+	//   can be shut down.
+
+	done := make(chan struct{})
+	close(c.outUnsorted)
+	go func() {
+		for {
+			select {
+			case m := <-c.outbox:
+				m.Ack()
+			case <-done:
+				return
+			}
 		}
-	}
+	}()
+	c.sortLoopDone.Wait()
+	done <- struct{}{}
+	log.Info("Messages have been drained.")
 }
diff --git a/fleetspeak/src/client/internal/message/retry.go b/fleetspeak/src/client/internal/message/retry.go
index 31c5dd74..e3356e0d 100644
--- a/fleetspeak/src/client/internal/message/retry.go
+++ b/fleetspeak/src/client/internal/message/retry.go
@@ -49,6 +49,7 @@ func RetryLoop(in <-chan service.AckMessage, out chan<- comms.MessageInfo, stats
 				if sm.m.Ack != nil {
 					sm.m.Ack()
 				}
+				stats.MessageAcknowledged(sm.m.M, sm.size)
 				acks <- sm
 			},
 			Nack: func() { nacks <- sm },
@@ -68,10 +69,9 @@ func RetryLoop(in <-chan service.AckMessage, out chan<- comms.MessageInfo, stats
 		case sm := <-acks:
 			size -= sm.size
 			count--
-			stats.MessageAcknowledged(sm.m.M, sm.size)
 		case sm := <-nacks:
-			out <- makeInfo(sm)
 			stats.BeforeMessageRetry(sm.m.M)
+			out <- makeInfo(sm)
 		case m, ok := <-optIn:
 			if !ok {
 				return
diff --git a/fleetspeak/src/client/internal/message/sort.go b/fleetspeak/src/client/internal/message/sort.go
index c15b6a5f..5f2614ca 100644
--- a/fleetspeak/src/client/internal/message/sort.go
+++ b/fleetspeak/src/client/internal/message/sort.go
@@ -24,14 +24,28 @@ import (
 )
 
 // SortLoop connects in and out in a sorted manner. That is, it acts essentially
-// as a buffered channel between in and out which sorts any messages within
-// it. Caller is responsible for implementing any needed size limit. Returns
-// when "in" is closed.
+// as a buffered channel between in and out which sorts any messages within it.
+// The caller is responsible for implementing any needed size limit.
+// SortLoop returns when in is closed, and the buffered messages have been
+// drained through out, to make sure no messages are lost.
 func SortLoop(in <-chan comms.MessageInfo, out chan<- comms.MessageInfo, f *flow.Filter) {
 	// Keep a slice of messages for each priority level. These are used as fifo
-	// queues, appending to the end and retreiving from head.
+	// queues, appending to the end and retrieving from head.
 	var low, medium, high []comms.MessageInfo
 
+	// Block until all messages have been drained.
+	defer func() {
+		for _, mi := range high {
+			out <- mi
+		}
+		for _, mi := range medium {
+			out <- mi
+		}
+		for _, mi := range low {
+			out <- mi
+		}
+	}()
+
 	// Append a message to the correct list.
 	appendMI := func(mi comms.MessageInfo) {
 		switch mi.M.Priority {