diff --git a/CHANGELOG.md b/CHANGELOG.md
index d3d758058..2b6738da1 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -19,5 +19,6 @@
 * [ENHANCEMENT] Add spanlogger package. #42
 * [ENHANCEMENT] Add runutil.CloseWithLogOnErr function. #58
 * [ENHANCEMENT] Optimise memberlist receive path when used as a backing store for rings with a large number of members. #76 #77
+* [ENHANCEMENT] Memberlist: prepare the data to send on the write before starting counting the elapsed time for `-memberlist.packet-write-timeout`, in order to reduce chances we hit the timeout when sending a packet to other node. #89
 * [BUGFIX] spanlogger: Support multiple tenant IDs. #59
 * [BUGFIX] Memberlist: fixed corrupted packets when sending compound messages with more than 255 messages or messages bigger than 64KB. #85
diff --git a/kv/memberlist/tcp_transport.go b/kv/memberlist/tcp_transport.go
index afbd1b201..c7e9b8aa9 100644
--- a/kv/memberlist/tcp_transport.go
+++ b/kv/memberlist/tcp_transport.go
@@ -439,16 +439,15 @@ func (t *TCPTransport) writeTo(b []byte, addr string) error {
 		}
 	}()
 
-	if t.cfg.PacketWriteTimeout > 0 {
-		deadline := time.Now().Add(t.cfg.PacketWriteTimeout)
-		err := c.SetDeadline(deadline)
-		if err != nil {
-			return fmt.Errorf("setting deadline: %v", err)
-		}
-	}
+	// Compute the digest *before* setting the deadline on the connection (so that the time
+	// it takes to compute the digest is not taken in account).
+	// We use md5 as quick and relatively short hash, not in cryptographic context.
+	// It's also used to detect if the whole packet has been received on the receiver side.
+	digest := md5.Sum(b)
 
-	buf := bytes.Buffer{}
-	buf.WriteByte(byte(packet))
+	// Prepare the header *before* setting the deadline on the connection.
+	headerBuf := bytes.Buffer{}
+	headerBuf.WriteByte(byte(packet))
 
 	// We need to send our address to the other side, otherwise other side can only see IP and port from TCP header.
 	// But that doesn't match our node address (new TCP connection has new random port), which confuses memberlist.
@@ -459,10 +458,18 @@ func (t *TCPTransport) writeTo(b []byte, addr string) error {
 		return fmt.Errorf("local address too long")
 	}
 
-	buf.WriteByte(byte(len(ourAddr)))
-	buf.WriteString(ourAddr)
+	headerBuf.WriteByte(byte(len(ourAddr)))
+	headerBuf.WriteString(ourAddr)
 
-	_, err = c.Write(buf.Bytes())
+	if t.cfg.PacketWriteTimeout > 0 {
+		deadline := time.Now().Add(t.cfg.PacketWriteTimeout)
+		err := c.SetDeadline(deadline)
+		if err != nil {
+			return fmt.Errorf("setting deadline: %v", err)
+		}
+	}
+
+	_, err = c.Write(headerBuf.Bytes())
 	if err != nil {
 		return fmt.Errorf("sending local address: %v", err)
 	}
@@ -475,9 +482,7 @@ func (t *TCPTransport) writeTo(b []byte, addr string) error {
 		return fmt.Errorf("sending data: short write")
 	}
 
-	// Append digest. We use md5 as quick and relatively short hash, not in cryptographic context.
-	// This helped to find some bugs, so let's keep it.
-	digest := md5.Sum(b)
+	// Append digest.
 	n, err = c.Write(digest[:])
 	if err != nil {
 		return fmt.Errorf("digest: %v", err)