diff --git a/stores/common.go b/stores/common.go
index 616f4f48..c460bb03 100644
--- a/stores/common.go
+++ b/stores/common.go
@@ -15,6 +15,7 @@ package stores
 
 import (
 	"sync"
+	"time"
 
 	"github.com/nats-io/nats-streaming-server/logger"
 	"github.com/nats-io/nats-streaming-server/spb"
@@ -337,6 +338,17 @@ func (gms *genericMsgStore) Close() error {
 	return nil
 }
 
+// With the given timestamp, returns in how long the message
+// should expire. If in the past, returns 0
+func (gms *genericMsgStore) msgExpireIn(timestamp int64) time.Duration {
+	now := time.Now().UnixNano()
+	fireIn := time.Duration(timestamp + int64(gms.limits.MaxAge) - now)
+	if fireIn < 0 {
+		fireIn = 0
+	}
+	return fireIn
+}
+
 ////////////////////////////////////////////////////////////////////////////
 // genericSubStore methods
 ////////////////////////////////////////////////////////////////////////////
diff --git a/stores/common_msg_test.go b/stores/common_msg_test.go
index 05d1fdc5..636ef8b3 100644
--- a/stores/common_msg_test.go
+++ b/stores/common_msg_test.go
@@ -495,6 +495,42 @@ func TestCSMaxAgeWithGapInSeq(t *testing.T) {
 	}
 }
 
+func TestCSMaxAgeForMsgsWithTimestampInPast(t *testing.T) {
+	for _, st := range testStores {
+		st := st
+		t.Run(st.name, func(t *testing.T) {
+			t.Parallel()
+			defer endTest(t, st)
+			s := startTest(t, st)
+			defer s.Close()
+
+			sl := testDefaultStoreLimits
+			sl.MaxAge = time.Minute
+			s.SetLimits(&sl)
+
+			cs := storeCreateChannel(t, s, "foo")
+			for seq := uint64(1); seq < 3; seq++ {
+				// Create a message with a timestamp in the past.
+				msg := &pb.MsgProto{
+					Sequence:  seq,
+					Subject:   "foo",
+					Data:      []byte("hello"),
+					Timestamp: time.Now().Add(-time.Hour).UnixNano(),
+				}
+				if _, err := cs.Msgs.Store(msg); err != nil {
+					t.Fatalf("Error storing message: %v", err)
+				}
+				// Wait a bit
+				time.Sleep(300 * time.Millisecond)
+				// Check that message has expired.
+				if first, err := cs.Msgs.FirstSequence(); err != nil || first != seq+1 {
+					t.Fatal("Message should have expired")
+				}
+			}
+		})
+	}
+}
+
 func TestCSGetSeqFromStartTime(t *testing.T) {
 	for _, st := range testStores {
 		st := st
diff --git a/stores/memstore.go b/stores/memstore.go
index 650a9926..51bda5be 100644
--- a/stores/memstore.go
+++ b/stores/memstore.go
@@ -107,7 +107,7 @@ func (ms *MemoryMsgStore) Store(m *pb.MsgProto) (uint64, error) {
 	// If there is an age limit and no timer yet created, do so now
 	if ms.limits.MaxAge > time.Duration(0) && ms.ageTimer == nil {
 		ms.wg.Add(1)
-		ms.ageTimer = time.AfterFunc(ms.limits.MaxAge, ms.expireMsgs)
+		ms.ageTimer = time.AfterFunc(ms.msgExpireIn(m.Timestamp), ms.expireMsgs)
 	}
 
 	// Check if we need to remove any (but leave at least the last added)
diff --git a/stores/sqlstore.go b/stores/sqlstore.go
index 24a1081b..809d748c 100644
--- a/stores/sqlstore.go
+++ b/stores/sqlstore.go
@@ -331,6 +331,7 @@ type SQLMsgStore struct {
 	channelID   int64
 	sqlStore    *SQLStore // Reference to "parent" store
 	expireTimer *time.Timer
+	fTimestamp  int64
 	wg          sync.WaitGroup
 
 	// If option NoBuffering is false, uses this cache for storing Store()
@@ -1407,8 +1408,9 @@ func (ms *SQLMsgStore) Store(m *pb.MsgProto) (uint64, error) {
 			return 0, sqlStmtError(sqlStoreMsg, err)
 		}
 	}
-	if ms.first == 0 {
+	if ms.first == 0 || ms.first == seq {
 		ms.first = seq
+		ms.fTimestamp = m.Timestamp
 	}
 	ms.last = seq
 	ms.totalCount++
@@ -1461,7 +1463,7 @@ func (ms *SQLMsgStore) Store(m *pb.MsgProto) (uint64, error) {
 
 func (ms *SQLMsgStore) createExpireTimer() {
 	ms.wg.Add(1)
-	ms.expireTimer = time.AfterFunc(ms.limits.MaxAge, ms.expireMsgs)
+	ms.expireTimer = time.AfterFunc(ms.msgExpireIn(ms.fTimestamp), ms.expireMsgs)
 }
 
 // Lookup implements the MsgStore interface
@@ -1563,7 +1565,6 @@ func (ms *SQLMsgStore) expireMsgs() {
 		count     int
 		maxSeq    uint64
 		totalSize uint64
-		timestamp int64
 	)
 	processErr := func(errCode int, err error) {
 		ms.log.Errorf("Unable to perform expiration for channel %q: %v", ms.subject, sqlStmtError(errCode, err))
@@ -1595,24 +1596,24 @@ func (ms *SQLMsgStore) expireMsgs() {
 			ms.totalBytes -= totalSize
 		}
 		// Reset since we are in a loop
-		timestamp = 0
+		ms.fTimestamp = 0
 		// If there is any message left in the channel, find out what the expiration
 		// timer needs to be set to.
 		if ms.totalCount > 0 {
 			r = ms.sqlStore.preparedStmts[sqlGetFirstMsgTimestamp].QueryRow(ms.channelID, ms.first)
-			if err := r.Scan(&timestamp); err != nil {
+			if err := r.Scan(&ms.fTimestamp); err != nil {
 				processErr(sqlGetFirstMsgTimestamp, err)
 				return
 			}
 		}
 		// No message left or no message to expire. The timer will be recreated when
 		// a new message is added to the channel.
-		if timestamp == 0 {
-			ms.wg.Done()
+		if ms.fTimestamp == 0 {
 			ms.expireTimer = nil
+			ms.wg.Done()
 			return
 		}
-		elapsed := time.Duration(time.Now().UnixNano() - timestamp)
+		elapsed := time.Duration(time.Now().UnixNano() - ms.fTimestamp)
 		if elapsed < ms.limits.MaxAge {
 			ms.expireTimer.Reset(ms.limits.MaxAge - elapsed)
 			// Done with the for loop
diff --git a/stores/sqlstore_test.go b/stores/sqlstore_test.go
index 7ea2850b..214301db 100644
--- a/stores/sqlstore_test.go
+++ b/stores/sqlstore_test.go
@@ -2095,3 +2095,48 @@ func TestSQLDeadlines(t *testing.T) {
 		return err
 	})
 }
+
+func TestSQLMaxAgeForMsgsWithTimestampInPast(t *testing.T) {
+	if !doSQL {
+		t.SkipNow()
+	}
+
+	cleanupSQLDatastore(t)
+	defer cleanupSQLDatastore(t)
+
+	// Create store with caching enabled (the no cache is handled in
+	// test TestCSMaxAgeForMsgsWithTimestampInPast).
+	s, err := NewSQLStore(testLogger, testSQLDriver, testSQLSource, nil, SQLNoCaching(false))
+	if err != nil {
+		t.Fatalf("Error creating store: %v", err)
+	}
+	defer s.Close()
+
+	sl := testDefaultStoreLimits
+	sl.MaxAge = time.Minute
+	s.SetLimits(&sl)
+
+	cs := storeCreateChannel(t, s, "foo")
+	for seq := uint64(1); seq < 3; seq++ {
+		// Create a message with a timestamp in the past.
+		msg := &pb.MsgProto{
+			Sequence:  seq,
+			Subject:   "foo",
+			Data:      []byte("hello"),
+			Timestamp: time.Now().Add(-time.Hour).UnixNano(),
+		}
+		if _, err := cs.Msgs.Store(msg); err != nil {
+			t.Fatalf("Error storing message: %v", err)
+		}
+		// With caching, timer is triggered on Flush().
+		if err := cs.Msgs.Flush(); err != nil {
+			t.Fatalf("Error on flush: %v", err)
+		}
+		// Wait a bit
+		time.Sleep(300 * time.Millisecond)
+		// Check that message has expired.
+		if first, err := cs.Msgs.FirstSequence(); err != nil || first != seq+1 {
+			t.Fatal("Message should have expired")
+		}
+	}
+}