diff --git a/server/client.go b/server/client.go
index 60c5e26c..e1ab4ffc 100644
--- a/server/client.go
+++ b/server/client.go
@@ -177,6 +177,7 @@ const (
 	MsgHeaderViolation
 	NoRespondersRequiresHeaders
 	ClusterNameConflict
+	DuplicateRemoteLeafnodeConnection
 )
 
 // Some flags passed to processMsgResults
diff --git a/server/leafnode.go b/server/leafnode.go
index f6b21fd4..72dad43e 100644
--- a/server/leafnode.go
+++ b/server/leafnode.go
@@ -836,7 +836,7 @@ func (s *Server) createLeafNode(conn net.Conn, remote *leafNodeCfg) *client {
 	if solicited {
 		// Make sure we register with the account here.
 		c.registerWithAccount(acc)
-		s.addLeafNodeConnection(c)
+		s.addLeafNodeConnection(c, _EMPTY_, false)
 		s.initLeafNodeSmapAndSendSubs(c)
 		if sendSysConnectEvent {
 			s.sendLeafNodeConnect(acc)
@@ -1006,14 +1006,53 @@ func (s *Server) setLeafNodeInfoHostPortAndIP() error {
 	return nil
 }
 
-func (s *Server) addLeafNodeConnection(c *client) {
+// Add the connection to the map of leaf nodes.
+// If `checkForDup` is true (invoked when a leafnode is accepted), then we check
+// if a connection already exists for the same server name (ID) and account.
+// That can happen when the remote is attempting to reconnect while the accepting
+// side did not detect the connection as broken yet.
+// But it can also happen when there is a misconfiguration and the remote is
+// creating two (or more) connections that bind to the same account on the accept
+// side.
+// When a duplicate is found, the new connection is accepted and the old is closed
+// (this solves the stale connection situation). An error is returned to help the
+// remote detect the misconfiguration when the duplicate is the result of that
+// misconfiguration.
+func (s *Server) addLeafNodeConnection(c *client, srvName string, checkForDup bool) {
+	var accName string
 	c.mu.Lock()
 	cid := c.cid
+	if c.acc != nil {
+		accName = c.acc.Name
+	}
 	c.mu.Unlock()
+
+	var old *client
 	s.mu.Lock()
+	if checkForDup {
+		for _, ol := range s.leafs {
+			ol.mu.Lock()
+			// We check for empty because in some test we may send empty CONNECT{}
+			if srvName != _EMPTY_ && ol.opts.Name == srvName && ol.acc.Name == accName {
+				old = ol
+			}
+			ol.mu.Unlock()
+			if old != nil {
+				break
+			}
+		}
+	}
+	// Store new connection in the map
 	s.leafs[cid] = c
 	s.mu.Unlock()
 	s.removeFromTempClients(cid)
+
+	// If applicable, evict the old one.
+	if old != nil {
+		old.sendErrAndErr(DuplicateRemoteLeafnodeConnection.String())
+		old.closeConnection(DuplicateRemoteLeafnodeConnection)
+		c.Warnf("Replacing connection from same server")
+	}
 }
 
 func (s *Server) removeLeafNodeConnection(c *client) {
@@ -1073,9 +1112,6 @@ func (c *client) processLeafNodeConnect(s *Server, arg []byte, lang string) erro
 		return ErrWrongGateway
 	}
 
-	// Check for stale connection from same server/account
-	c.replaceOldLeafNodeConnIfNeeded(s, proto)
-
 	// Leaf Nodes do not do echo or verbose or pedantic.
 	c.opts.Verbose = false
 	c.opts.Echo = false
@@ -1091,6 +1127,9 @@ func (c *client) processLeafNodeConnect(s *Server, arg []byte, lang string) erro
 		c.leaf.remoteCluster = proto.Cluster
 	}
 
+	// Add in the leafnode here since we passed through auth at this point.
+	s.addLeafNodeConnection(c, proto.Name, true)
+
 	// If we have permissions bound to this leafnode we need to send then back to the
 	// origin server for local enforcement.
 	s.sendPermsInfo(c)
@@ -1099,9 +1138,6 @@ func (c *client) processLeafNodeConnect(s *Server, arg []byte, lang string) erro
 	// This will send all registered subs too.
 	s.initLeafNodeSmapAndSendSubs(c)
 
-	// Add in the leafnode here since we passed through auth at this point.
-	s.addLeafNodeConnection(c)
-
 	// Announce the account connect event for a leaf node.
 	// This will no-op as needed.
 	s.sendLeafNodeConnect(c.acc)
@@ -1109,42 +1145,6 @@ func (c *client) processLeafNodeConnect(s *Server, arg []byte, lang string) erro
 	return nil
 }
 
-// Invoked from a server accepting a leafnode connection. It looks for a possible
-// existing leafnode connection from the same server with the same account, and
-// if it finds one, closes it so that the new one is accepted and not reported as
-// forming a cycle.
-//
-// This must be invoked for LEAF client types, and on the server accepting the connection.
-//
-// No server nor client lock held on entry.
-func (c *client) replaceOldLeafNodeConnIfNeeded(s *Server, connInfo *leafConnectInfo) {
-	var accName string
-	c.mu.Lock()
-	if c.acc != nil {
-		accName = c.acc.Name
-	}
-	c.mu.Unlock()
-
-	var old *client
-	s.mu.Lock()
-	for _, ol := range s.leafs {
-		ol.mu.Lock()
-		// We check for empty because in some test we may send empty CONNECT{}
-		if ol.opts.Name == connInfo.Name && connInfo.Name != _EMPTY_ && ol.acc.Name == accName {
-			old = ol
-		}
-		ol.mu.Unlock()
-		if old != nil {
-			break
-		}
-	}
-	s.mu.Unlock()
-	if old != nil {
-		old.Warnf("Replacing connection from same server")
-		old.closeConnection(ReadError)
-	}
-}
-
 // Returns the remote cluster name. This is set only once so does not require a lock.
 func (c *client) remoteCluster() string {
 	if c.leaf == nil {
diff --git a/server/leafnode_test.go b/server/leafnode_test.go
index e87b24d0..c4c01b68 100644
--- a/server/leafnode_test.go
+++ b/server/leafnode_test.go
@@ -1803,6 +1803,66 @@ func TestLeafNodeLoopDetectedDueToReconnect(t *testing.T) {
 	checkLeafNodeConnected(t, sl)
 }
 
+func TestLeafNodeTwoRemotesBindToSameAccount(t *testing.T) {
+	opts := DefaultOptions()
+	opts.LeafNode.Host = "127.0.0.1"
+	opts.LeafNode.Port = -1
+	s := RunServer(opts)
+	defer s.Shutdown()
+
+	conf := `
+	listen: 127.0.0.1:-1
+	cluster { name: ln22, listen: 127.0.0.1:-1 }
+	accounts {
+		a { users [ {user: a, password: a} ]}
+		b { users [ {user: b, password: b} ]}
+	}
+	leafnodes {
+		remotes = [
+			{
+				url: nats-leaf://127.0.0.1:%d
+				account: a
+			}
+			{
+				url: nats-leaf://127.0.0.1:%d
+				account: b
+			}
+		]
+	}
+	`
+	lconf := createConfFile(t, []byte(fmt.Sprintf(conf, opts.LeafNode.Port, opts.LeafNode.Port)))
+	defer os.Remove(lconf)
+
+	lopts, err := ProcessConfigFile(lconf)
+	if err != nil {
+		t.Fatalf("Error loading config file: %v", err)
+	}
+	lopts.NoLog = false
+	ln, err := NewServer(lopts)
+	if err != nil {
+		t.Fatalf("Error creating server: %v", err)
+	}
+	defer ln.Shutdown()
+	l := &captureErrorLogger{errCh: make(chan string, 10)}
+	ln.SetLogger(l, false, false)
+
+	wg := sync.WaitGroup{}
+	wg.Add(1)
+	go func() {
+		defer wg.Done()
+		ln.Start()
+	}()
+
+	select {
+	case err := <-l.errCh:
+		fmt.Printf("@@IK: err=%q\n", err)
+	case <-time.After(2 * time.Second):
+		t.Fatal("Did not get any error")
+	}
+	ln.Shutdown()
+	wg.Wait()
+}
+
 func TestLeafNodeNoDuplicateWithinCluster(t *testing.T) {
 	// This set the cluster name to "abc"
 	oSrv1 := DefaultOptions()
diff --git a/server/monitor.go b/server/monitor.go
index a1e3858b..4bae0fda 100644
--- a/server/monitor.go
+++ b/server/monitor.go
@@ -1913,6 +1913,8 @@ func (reason ClosedState) String() string {
 		return "No Responders Requires Headers"
 	case ClusterNameConflict:
 		return "Cluster Name Conflict"
+	case DuplicateRemoteLeafnodeConnection:
+		return "Duplicate Remote LeafNode Connection"
 	}
 
 	return "Unknown State"