diff --git a/exchange/bitswap/bitswap.go b/exchange/bitswap/bitswap.go
index fe6b8d7c497..dfa72ff2ff2 100644
--- a/exchange/bitswap/bitswap.go
+++ b/exchange/bitswap/bitswap.go
@@ -277,10 +277,16 @@ func (bs *bitswap) taskWorker(ctx context.Context) {
 		case <-ctx.Done():
 			log.Debugf("exiting")
 			return
-		case envelope := <-bs.engine.Outbox():
-			log.Debugf("message to %s sending...", envelope.Peer)
-			bs.send(ctx, envelope.Peer, envelope.Message)
-			log.Debugf("message to %s sent", envelope.Peer)
+		case nextEnvelope := <-bs.engine.Outbox():
+			select {
+			case <-ctx.Done():
+				return
+			case envelope, ok := <-nextEnvelope:
+				if !ok {
+					continue
+				}
+				bs.send(ctx, envelope.Peer, envelope.Message)
+			}
 		}
 	}
 }
diff --git a/exchange/bitswap/decision/engine.go b/exchange/bitswap/decision/engine.go
index ea0491c2c87..05687b3128f 100644
--- a/exchange/bitswap/decision/engine.go
+++ b/exchange/bitswap/decision/engine.go
@@ -44,7 +44,8 @@ import (
 var log = eventlog.Logger("engine")
 
 const (
-	sizeOutboxChan = 4
+	// outboxChanBuffer must be 0 to prevent stale messages from being sent
+	outboxChanBuffer = 0
 )
 
 // Envelope contains a message for a Peer
@@ -68,8 +69,9 @@ type Engine struct {
 	// that case, no lock would be required.
 	workSignal chan struct{}
 
-	// outbox contains outgoing messages to peers
-	outbox chan Envelope
+	// outbox contains outgoing messages to peers. This is owned by the
+	// taskWorker goroutine
+	outbox chan (<-chan *Envelope)
 
 	bs bstore.Blockstore
 
@@ -83,7 +85,7 @@ func NewEngine(ctx context.Context, bs bstore.Blockstore) *Engine {
 		ledgerMap:        make(map[peer.ID]*ledger),
 		bs:               bs,
 		peerRequestQueue: newPRQ(),
-		outbox:           make(chan Envelope, sizeOutboxChan),
+		outbox:           make(chan (<-chan *Envelope), outboxChanBuffer),
 		workSignal:       make(chan struct{}),
 	}
 	go e.taskWorker(ctx)
@@ -91,45 +93,55 @@ func NewEngine(ctx context.Context, bs bstore.Blockstore) *Engine {
 }
 
 func (e *Engine) taskWorker(ctx context.Context) {
-	log := log.Prefix("bitswap.Engine.taskWorker")
+	defer close(e.outbox) // because taskWorker uses the channel exclusively
+	for {
+		oneTimeUse := make(chan *Envelope, 1) // buffer to prevent blocking
+		select {
+		case <-ctx.Done():
+			return
+		case e.outbox <- oneTimeUse:
+		}
+		// receiver is ready for an outoing envelope. let's prepare one. first,
+		// we must acquire a task from the PQ...
+		envelope, err := e.nextEnvelope(ctx)
+		if err != nil {
+			close(oneTimeUse)
+			return // ctx cancelled
+		}
+		oneTimeUse <- envelope // buffered. won't block
+		close(oneTimeUse)
+	}
+}
+
+// nextEnvelope runs in the taskWorker goroutine. Returns an error if the
+// context is cancelled before the next Envelope can be created.
+func (e *Engine) nextEnvelope(ctx context.Context) (*Envelope, error) {
 	for {
 		nextTask := e.peerRequestQueue.Pop()
-		if nextTask == nil {
-			// No tasks in the list?
-			// Wait until there are!
+		for nextTask == nil {
 			select {
 			case <-ctx.Done():
-				log.Debugf("exiting: %s", ctx.Err())
-				return
+				return nil, ctx.Err()
 			case <-e.workSignal:
-				log.Debugf("woken up")
+				nextTask = e.peerRequestQueue.Pop()
 			}
-			continue
 		}
-		log := log.Prefix("%s", nextTask)
-		log.Debugf("processing")
+
+		// with a task in hand, we're ready to prepare the envelope...
 
 		block, err := e.bs.Get(nextTask.Entry.Key)
 		if err != nil {
-			log.Warning("engine: task exists to send block, but block is not in blockstore")
 			continue
 		}
-		// construct message here so we can make decisions about any additional
-		// information we may want to include at this time.
-		m := bsmsg.New()
+
+		m := bsmsg.New() // TODO: maybe add keys from our wantlist?
 		m.AddBlock(block)
-		// TODO: maybe add keys from our wantlist?
-		log.Debugf("sending...")
-		select {
-		case <-ctx.Done():
-			return
-		case e.outbox <- Envelope{Peer: nextTask.Target, Message: m}:
-			log.Debugf("sent")
-		}
+		return &Envelope{Peer: nextTask.Target, Message: m}, nil
 	}
 }
 
-func (e *Engine) Outbox() <-chan Envelope {
+// Outbox returns a channel of one-time use Envelope channels.
+func (e *Engine) Outbox() <-chan (<-chan *Envelope) {
 	return e.outbox
 }
 
diff --git a/exchange/bitswap/decision/engine_test.go b/exchange/bitswap/decision/engine_test.go
index b2583a020ee..8e5ab672c0b 100644
--- a/exchange/bitswap/decision/engine_test.go
+++ b/exchange/bitswap/decision/engine_test.go
@@ -1,6 +1,8 @@
 package decision
 
 import (
+	"errors"
+	"fmt"
 	"math"
 	"strings"
 	"sync"
@@ -104,7 +106,8 @@ func TestOutboxClosedWhenEngineClosed(t *testing.T) {
 	var wg sync.WaitGroup
 	wg.Add(1)
 	go func() {
-		for _ = range e.Outbox() {
+		for nextEnvelope := range e.Outbox() {
+			<-nextEnvelope
 		}
 		wg.Done()
 	}()
@@ -116,6 +119,10 @@ func TestOutboxClosedWhenEngineClosed(t *testing.T) {
 }
 
 func TestPartnerWantsThenCancels(t *testing.T) {
+	numRounds := 10
+	if testing.Short() {
+		numRounds = 1
+	}
 	alphabet := strings.Split("abcdefghijklmnopqrstuvwxyz", "")
 	vowels := strings.Split("aeiou", "")
 
@@ -129,23 +136,31 @@ func TestPartnerWantsThenCancels(t *testing.T) {
 		},
 	}
 
-	for _, testcase := range testcases {
-		set := testcase[0]
-		cancels := testcase[1]
-		keeps := stringsComplement(set, cancels)
-
-		bs := blockstore.NewBlockstore(dssync.MutexWrap(ds.NewMapDatastore()))
-		e := NewEngine(context.Background(), bs)
-		partner := testutil.RandPeerIDFatal(t)
-		for _, letter := range set {
-			block := blocks.NewBlock([]byte(letter))
-			bs.Put(block)
+	bs := blockstore.NewBlockstore(dssync.MutexWrap(ds.NewMapDatastore()))
+	for _, letter := range alphabet {
+		block := blocks.NewBlock([]byte(letter))
+		if err := bs.Put(block); err != nil {
+			t.Fatal(err)
 		}
-		partnerWants(e, set, partner)
-		partnerCancels(e, cancels, partner)
-		assertPoppedInOrder(t, e, keeps)
 	}
 
+	for i := 0; i < numRounds; i++ {
+		for _, testcase := range testcases {
+			set := testcase[0]
+			cancels := testcase[1]
+			keeps := stringsComplement(set, cancels)
+
+			e := NewEngine(context.Background(), bs)
+			partner := testutil.RandPeerIDFatal(t)
+
+			partnerWants(e, set, partner)
+			partnerCancels(e, cancels, partner)
+			if err := checkHandledInOrder(t, e, keeps); err != nil {
+				t.Logf("run #%d of %d", i, numRounds)
+				t.Fatal(err)
+			}
+		}
+	}
 }
 
 func partnerWants(e *Engine, keys []string, partner peer.ID) {
@@ -166,15 +181,17 @@ func partnerCancels(e *Engine, keys []string, partner peer.ID) {
 	e.MessageReceived(partner, cancels)
 }
 
-func assertPoppedInOrder(t *testing.T, e *Engine, keys []string) {
+func checkHandledInOrder(t *testing.T, e *Engine, keys []string) error {
 	for _, k := range keys {
-		envelope := <-e.Outbox()
+		next := <-e.Outbox()
+		envelope := <-next
 		received := envelope.Message.Blocks()[0]
 		expected := blocks.NewBlock([]byte(k))
 		if received.Key() != expected.Key() {
-			t.Fatal("received", string(received.Data), "expected", string(expected.Data))
+			return errors.New(fmt.Sprintln("received", string(received.Data), "expected", string(expected.Data)))
 		}
 	}
+	return nil
 }
 
 func stringsComplement(set, subset []string) []string {