diff --git a/server/clustering_test.go b/server/clustering_test.go
index 43923c0b..5aee5e8b 100644
--- a/server/clustering_test.go
+++ b/server/clustering_test.go
@@ -6627,11 +6627,12 @@ type blockingLookupStore struct {
 }
 
 func (b *blockingLookupStore) Lookup(seq uint64) (*pb.MsgProto, error) {
+	msg, err := b.MsgStore.Lookup(seq)
 	if !b.skip {
 		b.inLookupCh <- struct{}{}
 		b.skip = <-b.releaseCh
 	}
-	return b.MsgStore.Lookup(seq)
+	return msg, err
 }
 
 func TestClusteringRestoreSnapshotErrorDontSkipSeq(t *testing.T) {
diff --git a/server/server.go b/server/server.go
index d17235db..eea59aae 100644
--- a/server/server.go
+++ b/server/server.go
@@ -5169,7 +5169,7 @@ func (s *StanServer) sendAvailableMessages(c *channel, sub *subState) {
 }
 
 func (s *StanServer) getNextMsg(c *channel, nextSeq, lastSent *uint64) *pb.MsgProto {
-	for {
+	for i := 0; ; i++ {
 		nextMsg, err := c.store.Msgs.Lookup(*nextSeq)
 		if err != nil {
 			s.log.Errorf("Error looking up message %v:%v (%v)", c.name, *nextSeq, err)
@@ -5180,13 +5180,33 @@ func (s *StanServer) getNextMsg(c *channel, nextSeq, lastSent *uint64) *pb.MsgPr
 		if nextMsg != nil {
 			return nextMsg
 		}
+		// Message was not found, check the store first/last sequences.
 		first, last, _ := c.store.Msgs.FirstAndLastSequence()
-		if *nextSeq < first {
+		if *nextSeq >= last {
+			// This means that we are looking for a message that has not
+			// been stored. This is perfectly normal when delivering messages
+			// and reach the end of the channel.
+			return nil
+		} else if *nextSeq < first {
+			// We were trying to lookup a message that has likely now
+			// been removed (expired, or due to max msgs/bytes etc) since
+			// the first available is greater than the message we were
+			// looking for. Try to lookup the first available.
 			*nextSeq = first
 			*lastSent = first - 1
-		} else if *nextSeq >= last {
-			return nil
-		} else {
+		} else if i > 0 {
+			// The last condition is when `nextSeq` is between `first` and
+			// `last`, which could mean 2 things:
+			// - New messages have been stored between the lookup at the top
+			//   of the loop and calling FirstAndLastSequence(), so we should
+			//   try again.
+			// - There is a gap - which should not happen but we have decided
+			//   to support this situation - so we move by one at a time until
+			//   we find a valid message.
+
+			// So if i==0 (first iteration) we don't come here and simply try
+			// again. Otherwise, move the requested sequence in search of the
+			// first valid message.
 			*nextSeq++
 			*lastSent++
 		}
diff --git a/server/server_delivery_test.go b/server/server_delivery_test.go
index adb2fc81..50f19cde 100644
--- a/server/server_delivery_test.go
+++ b/server/server_delivery_test.go
@@ -15,6 +15,7 @@ package server
 
 import (
 	"fmt"
+	"sync"
 	"sync/atomic"
 	"testing"
 	"time"
@@ -324,3 +325,60 @@ func TestPersistentStoreSQLSubsPendingRows(t *testing.T) {
 	}
 	waitForAcks(t, s, clientName, 1, 3002)
 }
+
+func TestDeliveryRaceBetweenNextMsgAndStoring(t *testing.T) {
+	s := runServer(t, clusterName)
+	defer s.Shutdown()
+
+	sc := NewDefaultConnection(t)
+	defer sc.Close()
+
+	prev := uint64(0)
+	errCh := make(chan error, 1)
+	doneCh := make(chan bool)
+	cb := func(m *stan.Msg) {
+		if m.Sequence != prev+1 {
+			errCh <- fmt.Errorf("Previous was %v, now got %v", prev, m.Sequence)
+			m.Sub.Close()
+			return
+		}
+		prev = m.Sequence
+		if m.Sequence == 4 {
+			doneCh <- true
+		}
+	}
+	if _, err := sc.Subscribe("foo", cb, stan.MaxInflight(1)); err != nil {
+		t.Fatalf("Erro on subscribe: %v", err)
+	}
+
+	sc.Publish("foo", []byte("msg1"))
+
+	c := s.channels.get("foo")
+	ch1 := make(chan struct{})
+	ch2 := make(chan bool)
+	c.store.Msgs = &blockingLookupStore{MsgStore: c.store.Msgs, inLookupCh: ch1, releaseCh: ch2}
+
+	sub := s.clients.getSubs(clientName)[0]
+	wg := sync.WaitGroup{}
+	wg.Add(1)
+	go func() {
+		s.sendAvailableMessages(c, sub)
+		wg.Done()
+	}()
+	<-ch1
+	sc.PublishAsync("foo", []byte("msg2"), nil)
+	sc.PublishAsync("foo", []byte("msg3"), nil)
+	time.Sleep(50 * time.Millisecond)
+	ch2 <- true
+	wg.Wait()
+
+	sc.Publish("foo", []byte("msg4"))
+
+	select {
+	case <-doneCh:
+	case e := <-errCh:
+		t.Fatal(e.Error())
+	case <-time.After(time.Second):
+		t.Fatal("Timeout!")
+	}
+}