diff --git a/decision/bench_test.go b/decision/bench_test.go
index dc3aea06..46d40ce0 100644
--- a/decision/bench_test.go
+++ b/decision/bench_test.go
@@ -25,6 +25,6 @@ func BenchmarkTaskQueuePush(b *testing.B) {
 	for i := 0; i < b.N; i++ {
 		c := cid.NewCidV0(u.Hash([]byte(fmt.Sprint(i))))
 
-		q.Push(&wantlist.Entry{Cid: c, Priority: math.MaxInt32}, peers[i%len(peers)])
+		q.Push(peers[i%len(peers)], &wantlist.Entry{Cid: c, Priority: math.MaxInt32})
 	}
 }
diff --git a/decision/engine.go b/decision/engine.go
index 736e5d46..8126555f 100644
--- a/decision/engine.go
+++ b/decision/engine.go
@@ -52,6 +52,8 @@ var log = logging.Logger("engine")
 const (
 	// outboxChanBuffer must be 0 to prevent stale messages from being sent
 	outboxChanBuffer = 0
+	// maxMessageSize is the maximum size of the batched payload
+	maxMessageSize = 512 * 1024
 )
 
 // Envelope contains a message for a Peer
@@ -59,8 +61,8 @@ type Envelope struct {
 	// Peer is the intended recipient
 	Peer peer.ID
 
-	// Block is the payload
-	Block blocks.Block
+	// Message is the payload
+	Message bsmsg.BitSwapMessage
 
 	// A callback to notify the decision queue that the task is complete
 	Sent func()
@@ -166,21 +168,28 @@ func (e *Engine) nextEnvelope(ctx context.Context) (*Envelope, error) {
 		}
 
 		// with a task in hand, we're ready to prepare the envelope...
+		msg := bsmsg.New(true)
+		for _, entry := range nextTask.Entries {
+			block, err := e.bs.Get(entry.Cid)
+			if err != nil {
+				log.Errorf("tried to execute a task and errored fetching block: %s", err)
+				continue
+			}
+			msg.AddBlock(block)
+		}
 
-		block, err := e.bs.Get(nextTask.Entry.Cid)
-		if err != nil {
-			log.Errorf("tried to execute a task and errored fetching block: %s", err)
+		if msg.Empty() {
 			// If we don't have the block, don't hold that against the peer
 			// make sure to update that the task has been 'completed'
-			nextTask.Done()
+			nextTask.Done(nextTask.Entries)
 			continue
 		}
 
 		return &Envelope{
-			Peer:  nextTask.Target,
-			Block: block,
+			Peer:    nextTask.Target,
+			Message: msg,
 			Sent: func() {
-				nextTask.Done()
+				nextTask.Done(nextTask.Entries)
 				select {
 				case e.workSignal <- struct{}{}:
 					// work completing may mean that our queue will provide new
@@ -231,6 +240,8 @@ func (e *Engine) MessageReceived(p peer.ID, m bsmsg.BitSwapMessage) error {
 		l.wantList = wl.New()
 	}
 
+	var blockSize, msgSize int
+	var activeEntries []*wl.Entry
 	for _, entry := range m.Wantlist() {
 		if entry.Cancel {
 			log.Debugf("%s cancel %s", p, entry.Cid)
@@ -240,12 +251,24 @@ func (e *Engine) MessageReceived(p peer.ID, m bsmsg.BitSwapMessage) error {
 			log.Debugf("wants %s - %d", entry.Cid, entry.Priority)
 			l.Wants(entry.Cid, entry.Priority)
 			if exists, err := e.bs.Has(entry.Cid); err == nil && exists {
-				e.peerRequestQueue.Push(entry.Entry, p)
 				newWorkExists = true
+				if blockSize, err = e.bs.GetSize(entry.Cid); err != nil {
+					log.Error(err)
+					continue
+				}
+				if msgSize + blockSize > maxMessageSize {
+					e.peerRequestQueue.Push(p, activeEntries...)
+					activeEntries = []*wl.Entry{}
+					msgSize = 0
+				}
+				activeEntries = append(activeEntries, entry.Entry)
+				msgSize += blockSize
 			}
 		}
 	}
-
+	if len(activeEntries) > 0 {
+		e.peerRequestQueue.Push(p, activeEntries...)
+	}
 	for _, block := range m.Blocks() {
 		log.Debugf("got block %s %d bytes", block, len(block.RawData()))
 		l.ReceivedBytes(len(block.RawData()))
@@ -259,7 +282,7 @@ func (e *Engine) addBlock(block blocks.Block) {
 	for _, l := range e.ledgerMap {
 		l.lk.Lock()
 		if entry, ok := l.WantListContains(block.Cid()); ok {
-			e.peerRequestQueue.Push(entry, l.Partner)
+			e.peerRequestQueue.Push(l.Partner, entry)
 			work = true
 		}
 		l.lk.Unlock()
diff --git a/decision/engine_test.go b/decision/engine_test.go
index ed7d1055..54dd935c 100644
--- a/decision/engine_test.go
+++ b/decision/engine_test.go
@@ -191,7 +191,7 @@ func checkHandledInOrder(t *testing.T, e *Engine, keys []string) error {
 	for _, k := range keys {
 		next := <-e.Outbox()
 		envelope := <-next
-		received := envelope.Block
+		received := envelope.Message.Blocks()[0]
 		expected := blocks.NewBlock([]byte(k))
 		if !received.Cid().Equals(expected.Cid()) {
 			return errors.New(fmt.Sprintln("received", string(received.RawData()), "expected", string(expected.RawData())))
diff --git a/decision/peer_request_queue.go b/decision/peer_request_queue.go
index b9e34763..2b81e610 100644
--- a/decision/peer_request_queue.go
+++ b/decision/peer_request_queue.go
@@ -14,7 +14,7 @@ import (
 type peerRequestQueue interface {
 	// Pop returns the next peerRequestTask. Returns nil if the peerRequestQueue is empty.
 	Pop() *peerRequestTask
-	Push(entry *wantlist.Entry, to peer.ID)
+	Push(to peer.ID, entries ...*wantlist.Entry)
 	Remove(k *cid.Cid, p peer.ID)
 
 	// NB: cannot expose simply expose taskQueue.Len because trashed elements
@@ -46,7 +46,7 @@ type prq struct {
 }
 
 // Push currently adds a new peerRequestTask to the end of the list
-func (tl *prq) Push(entry *wantlist.Entry, to peer.ID) {
+func (tl *prq) Push(to peer.ID, entries ...*wantlist.Entry) {
 	tl.lock.Lock()
 	defer tl.lock.Unlock()
 	partner, ok := tl.partners[to]
@@ -58,31 +58,45 @@ func (tl *prq) Push(entry *wantlist.Entry, to peer.ID) {
 
 	partner.activelk.Lock()
 	defer partner.activelk.Unlock()
-	if partner.activeBlocks.Has(entry.Cid) {
-		return
+
+	newEntries := make([]*wantlist.Entry, 0, len(entries))
+	for _, entry := range entries {
+		if partner.activeBlocks.Has(entry.Cid) {
+			continue
+		}
+		if task, ok := tl.taskMap[taskEntryKey(to, entry.Cid)]; ok {
+			if task.Priority > entry.Priority {
+				task.Priority = entry.Priority
+				partner.taskQueue.Update(task.index)
+			}
+			continue
+		}
+		newEntries = append(newEntries, entry)
 	}
 
-	if task, ok := tl.taskMap[taskKey(to, entry.Cid)]; ok {
-		task.Entry.Priority = entry.Priority
-		partner.taskQueue.Update(task.index)
+	if len(newEntries) == 0 {
 		return
 	}
 
 	task := &peerRequestTask{
-		Entry:   entry,
+		Entries: newEntries,
 		Target:  to,
 		created: time.Now(),
-		Done: func() {
+		Done: func(e []*wantlist.Entry) {
 			tl.lock.Lock()
-			partner.TaskDone(entry.Cid)
+			for _, entry := range e {
+				partner.TaskDone(entry.Cid)
+			}
 			tl.pQueue.Update(partner.Index())
 			tl.lock.Unlock()
 		},
 	}
 
 	partner.taskQueue.Push(task)
-	tl.taskMap[task.Key()] = task
-	partner.requests++
+	for _, entry := range newEntries {
+		tl.taskMap[taskEntryKey(to, entry.Cid)] = task
+	}
+	partner.requests += len(newEntries)
 	tl.pQueue.Update(partner.Index())
 }
 
@@ -98,14 +112,23 @@ func (tl *prq) Pop() *peerRequestTask {
 	var out *peerRequestTask
 	for partner.taskQueue.Len() > 0 && partner.freezeVal == 0 {
 		out = partner.taskQueue.Pop().(*peerRequestTask)
-		delete(tl.taskMap, out.Key())
-		if out.trash {
-			out = nil
-			continue // discarding tasks that have been removed
-		}
 
-		partner.StartTask(out.Entry.Cid)
-		partner.requests--
+		newEntries := make([]*wantlist.Entry, 0, len(out.Entries))
+		for _, entry := range out.Entries {
+			delete(tl.taskMap, taskEntryKey(out.Target, entry.Cid))
+			if entry.Trash {
+				continue
+			}
+			partner.requests--
+			partner.StartTask(entry.Cid)
+			newEntries = append(newEntries, entry)
+		}
+		if len(newEntries) > 0 {
+			out.Entries = newEntries
+		} else {
+			out = nil // discarding tasks that have been removed
+			continue
+		}
 		break // and return |out|
 	}
 
@@ -116,12 +139,17 @@ func (tl *prq) Pop() *peerRequestTask {
 // Remove removes a task from the queue
 func (tl *prq) Remove(k *cid.Cid, p peer.ID) {
 	tl.lock.Lock()
-	t, ok := tl.taskMap[taskKey(p, k)]
+	t, ok := tl.taskMap[taskEntryKey(p, k)]
 	if ok {
-		// remove the task "lazily"
-		// simply mark it as trash, so it'll be dropped when popped off the
-		// queue.
-		t.trash = true
+		for _, entry := range t.Entries {
+			if entry.Cid == k {
+				// remove the task "lazily"
+				// simply mark it as trash, so it'll be dropped when popped off the
+				// queue.
+				entry.Trash = true
+				break
+			}
+		}
 
 		// having canceled a block, we now account for that in the given partner
 		partner := tl.partners[p]
@@ -166,14 +194,13 @@ func (tl *prq) thawRound() {
 }
 
 type peerRequestTask struct {
-	Entry  *wantlist.Entry
-	Target peer.ID
+	Entries  []*wantlist.Entry
+	Priority int
+	Target   peer.ID
 
 	// A callback to signal that this task has been completed
-	Done func()
+	Done func([]*wantlist.Entry)
 
-	// trash in a book-keeping field
-	trash bool
 	// created marks the time that the task was added to the queue
 	created time.Time
 	index   int // book-keeping field used by the pq container
@@ -181,7 +208,7 @@ type peerRequestTask struct {
 
 // Key uniquely identifies a task.
 func (t *peerRequestTask) Key() string {
-	return taskKey(t.Target, t.Entry.Cid)
+	return taskKey(t.Target, t.Entries)
 }
 
 // Index implements pq.Elem
@@ -195,7 +222,16 @@ func (t *peerRequestTask) SetIndex(i int) {
 }
 
 // taskKey returns a key that uniquely identifies a task.
-func taskKey(p peer.ID, k *cid.Cid) string {
+func taskKey(p peer.ID, entries []*wantlist.Entry) string {
+	key := string(p)
+	for _, entry := range entries {
+		key += entry.Cid.KeyString()
+	}
+	return key
+}
+
+// taskEntryKey returns a key that uniquely identifies a task.
+func taskEntryKey(p peer.ID, k *cid.Cid) string {
 	return string(p) + k.KeyString()
 }
 
@@ -208,7 +244,7 @@ var FIFO = func(a, b *peerRequestTask) bool {
 // different peers, the oldest task is prioritized.
 var V1 = func(a, b *peerRequestTask) bool {
 	if a.Target == b.Target {
-		return a.Entry.Priority > b.Entry.Priority
+		return a.Priority > b.Priority
 	}
 	return FIFO(a, b)
 }
diff --git a/decision/peer_request_queue_test.go b/decision/peer_request_queue_test.go
index 32e93a27..d6ad8989 100644
--- a/decision/peer_request_queue_test.go
+++ b/decision/peer_request_queue_test.go
@@ -45,7 +45,7 @@ func TestPushPop(t *testing.T) {
 		t.Log(partner.String())
 
 		c := cid.NewCidV0(u.Hash([]byte(letter)))
-		prq.Push(&wantlist.Entry{Cid: c, Priority: math.MaxInt32 - index}, partner)
+		prq.Push(partner, &wantlist.Entry{Cid: c, Priority: math.MaxInt32 - index})
 	}
 	for _, consonant := range consonants {
 		c := cid.NewCidV0(u.Hash([]byte(consonant)))
@@ -61,7 +61,9 @@ func TestPushPop(t *testing.T) {
 			break
 		}
 
-		out = append(out, received.Entry.Cid.String())
+		for _, entry := range received.Entries {
+			out = append(out, entry.Cid.String())
+		}
 	}
 
 	// Entries popped should already be in correct order
@@ -85,10 +87,10 @@ func TestPeerRepeats(t *testing.T) {
 
 	for i := 0; i < 5; i++ {
 		elcid := cid.NewCidV0(u.Hash([]byte(fmt.Sprint(i))))
-		prq.Push(&wantlist.Entry{Cid: elcid}, a)
-		prq.Push(&wantlist.Entry{Cid: elcid}, b)
-		prq.Push(&wantlist.Entry{Cid: elcid}, c)
-		prq.Push(&wantlist.Entry{Cid: elcid}, d)
+		prq.Push(a, &wantlist.Entry{Cid: elcid})
+		prq.Push(b, &wantlist.Entry{Cid: elcid})
+		prq.Push(c, &wantlist.Entry{Cid: elcid})
+		prq.Push(d, &wantlist.Entry{Cid: elcid})
 	}
 
 	// now, pop off four entries, there should be one from each
@@ -117,7 +119,7 @@ func TestPeerRepeats(t *testing.T) {
 	for blockI := 0; blockI < 4; blockI++ {
 		for i := 0; i < 4; i++ {
 			// its okay to mark the same task done multiple times here (JUST FOR TESTING)
-			tasks[i].Done()
+			tasks[i].Done(tasks[i].Entries)
 
 			ntask := prq.Pop()
 			if ntask.Target != tasks[i].Target {
diff --git a/wantlist/wantlist.go b/wantlist/wantlist.go
index beb4ac75..a7b02fcc 100644
--- a/wantlist/wantlist.go
+++ b/wantlist/wantlist.go
@@ -24,6 +24,8 @@ type Entry struct {
 	Priority int
 
 	SesTrk map[uint64]struct{}
+	// Trash in a book-keeping field
+	Trash bool
 }
 
 // NewRefEntry creates a new reference tracked wantlist entry
diff --git a/wantmanager.go b/wantmanager.go
index 380d8538..7db5aaf3 100644
--- a/wantmanager.go
+++ b/wantmanager.go
@@ -114,16 +114,20 @@ func (pm *WantManager) ConnectedPeers() []peer.ID {
 	return <-resp
 }
 
-func (pm *WantManager) SendBlock(ctx context.Context, env *engine.Envelope) {
+func (pm *WantManager) SendBlocks(ctx context.Context, env *engine.Envelope) {
 	// Blocks need to be sent synchronously to maintain proper backpressure
 	// throughout the network stack
 	defer env.Sent()
 
-	pm.sentHistogram.Observe(float64(len(env.Block.RawData())))
-
+	msgSize := 0
 	msg := bsmsg.New(false)
-	msg.AddBlock(env.Block)
-	log.Infof("Sending block %s to %s", env.Block, env.Peer)
+	for _, block := range env.Message.Blocks() {
+		msgSize += len(block.RawData())
+		msg.AddBlock(block)
+		log.Infof("Sending block %s to %s", block, env.Peer)
+	}
+
+	pm.sentHistogram.Observe(float64(msgSize))
 	err := pm.network.SendMessage(ctx, env.Peer, msg)
 	if err != nil {
 		log.Infof("sendblock error: %s", err)
diff --git a/workers.go b/workers.go
index 8f5e6edd..e1569288 100644
--- a/workers.go
+++ b/workers.go
@@ -59,24 +59,27 @@ func (bs *Bitswap) taskWorker(ctx context.Context, id int) {
 				if !ok {
 					continue
 				}
-				log.Event(ctx, "Bitswap.TaskWorker.Work", logging.LoggableF(func() map[string]interface{} {
-					return logging.LoggableMap{
-						"ID":     id,
-						"Target": envelope.Peer.Pretty(),
-						"Block":  envelope.Block.Cid().String(),
-					}
-				}))
-
 				// update the BS ledger to reflect sent message
 				// TODO: Should only track *useful* messages in ledger
 				outgoing := bsmsg.New(false)
-				outgoing.AddBlock(envelope.Block)
+				for _, block := range envelope.Message.Blocks() {
+					log.Event(ctx, "Bitswap.TaskWorker.Work", logging.LoggableF(func() map[string]interface{} {
+						return logging.LoggableMap{
+							"ID":     id,
+							"Target": envelope.Peer.Pretty(),
+							"Block":  block.Cid().String(),
+						}
+					}))
+					outgoing.AddBlock(block)
+				}
 				bs.engine.MessageSent(envelope.Peer, outgoing)
 
-				bs.wm.SendBlock(ctx, envelope)
+				bs.wm.SendBlocks(ctx, envelope)
 				bs.counterLk.Lock()
-				bs.counters.blocksSent++
-				bs.counters.dataSent += uint64(len(envelope.Block.RawData()))
+				for _, block := range envelope.Message.Blocks() {
+					bs.counters.blocksSent++
+					bs.counters.dataSent += uint64(len(block.RawData()))
+				}
 				bs.counterLk.Unlock()
 			case <-ctx.Done():
 				return