diff --git a/internal/ocsp/ocsp.go b/internal/ocsp/ocsp.go
index 8beab9d3c16..3110cc9d58a 100644
--- a/internal/ocsp/ocsp.go
+++ b/internal/ocsp/ocsp.go
@@ -1,4 +1,4 @@
-// Copyright 2019-2021 The NATS Authors
+// Copyright 2019-2024 The NATS Authors
 // Licensed under the Apache License, Version 2.0 (the "License");
 // you may not use this file except in compliance with the License.
 // You may obtain a copy of the License at
diff --git a/server/gateway.go b/server/gateway.go
index 65769546892..165f797f5bd 100644
--- a/server/gateway.go
+++ b/server/gateway.go
@@ -816,6 +816,14 @@ func (s *Server) createGateway(cfg *gatewayCfg, url *url.URL, conn net.Conn) {
 			tlsConfig = cfg.TLSConfig.Clone()
 			timeout = cfg.TLSTimeout
 			cfg.RUnlock()
+
+			// Ensure that OCSP callbacks are always setup on gateway reconnect.
+			if (opts.Gateway.TLSConfig.GetClientCertificate != nil && tlsConfig.GetClientCertificate == nil) {
+				tlsConfig.GetClientCertificate = opts.Gateway.TLSConfig.GetClientCertificate
+			}
+			if (opts.Gateway.TLSConfig.VerifyConnection != nil && tlsConfig.VerifyConnection == nil) {
+				tlsConfig.VerifyConnection = opts.Gateway.TLSConfig.VerifyConnection
+			}
 		} else {
 			tlsConfig = opts.Gateway.TLSConfig
 			timeout = opts.Gateway.TLSTimeout
diff --git a/server/gateway_test.go b/server/gateway_test.go
index e85f2956d1a..b5796828f19 100644
--- a/server/gateway_test.go
+++ b/server/gateway_test.go
@@ -6954,13 +6954,18 @@ func TestGatewayConnectEvents(t *testing.T) {
 	checkEvents(t, "Queued", true)
 }
 
-func disconnectInboundGatewaysAsStale(s *Server) {
+func disconnectInboundGateways(s *Server) {
 	s.gateway.RLock()
 	in := s.gateway.in
 	s.gateway.RUnlock()
+
+	s.gateway.RLock()
 	for _, client := range in {
-		client.closeConnection(StaleConnection)
+		s.gateway.RUnlock()
+		client.closeConnection(ClientClosed)
+		s.gateway.RLock()
 	}
+	s.gateway.RUnlock()
 }
 
 type testMissingOCSPStapleLogger struct {
@@ -6978,7 +6983,7 @@ func (l *testMissingOCSPStapleLogger) Errorf(format string, v ...interface{}) {
 	}
 }
 
-func TestOCSPGatewayMissingPeerStaple(t *testing.T) {
+func TestOCSPGatewayMissingPeerStapleIssue(t *testing.T) {
 	const (
 		caCert = "../test/configs/certs/ocsp/ca-cert.pem"
 		caKey  = "../test/configs/certs/ocsp/ca-key.pem"
@@ -7072,6 +7077,7 @@ func TestOCSPGatewayMissingPeerStaple(t *testing.T) {
 				name: "A"
 				url: "nats://127.0.0.1:%d"
 			}]
+
 			tls {
 				cert_file: "../test/configs/certs/ocsp/server-status-request-url-04-cert.pem"
 				key_file: "../test/configs/certs/ocsp/server-status-request-url-04-key.pem"
@@ -7136,7 +7142,7 @@ func TestOCSPGatewayMissingPeerStaple(t *testing.T) {
 
 	////////////////////////////////////////////////////////////////////////////
 	//                                                                        //
-	//  A and B are connected at this point and C is starting with certs that //
+	//  A and B are connected at this point and A is starting with certs that //
 	//  will be rotated.
 	//                                                                        //
 	////////////////////////////////////////////////////////////////////////////
@@ -7233,7 +7239,7 @@ func TestOCSPGatewayMissingPeerStaple(t *testing.T) {
 	}
 
 	// Reload and disconnect very fast trying to produce the race.
-	ctx, cancel = context.WithTimeout(context.Background(), 30*time.Second)
+	ctx, cancel = context.WithTimeout(context.Background(), 15*time.Second)
 	defer cancel()
 
 	// Swap logger from server to capture the missing peer log.
@@ -7244,9 +7250,18 @@ func TestOCSPGatewayMissingPeerStaple(t *testing.T) {
 	srvB.SetLogger(lB, false, false)
 
 	lC := &testMissingOCSPStapleLogger{ch: make(chan string, 30)}
-	srvB.SetLogger(lC, false, false)
+	srvC.SetLogger(lC, false, false)
+
+	// Start with a reload from the last server that connected directly to A.
+	if err := srvC.Reload(); err != nil {
+		t.Fatal(err)
+	}
 
+	// Stress reconnections and reloading servers without getting
+	// missing OCSP peer staple errors.
 	var wg sync.WaitGroup
+
+	wg.Add(1)
 	go func() {
 		for range time.NewTicker(500 * time.Millisecond).C {
 			select {
@@ -7255,11 +7270,11 @@ func TestOCSPGatewayMissingPeerStaple(t *testing.T) {
 				return
 			default:
 			}
-			disconnectInboundGatewaysAsStale(srvC)
+			disconnectInboundGateways(srvA)
 		}
 	}()
-	wg.Add(1)
 
+	wg.Add(1)
 	go func() {
 		for range time.NewTicker(500 * time.Millisecond).C {
 			select {
@@ -7268,13 +7283,26 @@ func TestOCSPGatewayMissingPeerStaple(t *testing.T) {
 				return
 			default:
 			}
-			disconnectInboundGatewaysAsStale(srvA)
+			disconnectInboundGateways(srvB)
 		}
 	}()
+
 	wg.Add(1)
+	go func() {
+		for range time.NewTicker(500 * time.Millisecond).C {
+			select {
+			case <-ctx.Done():
+				wg.Done()
+				return
+			default:
+			}
+			disconnectInboundGateways(srvC)
+		}
+	}()
 
+	wg.Add(1)
 	go func() {
-		for range time.NewTicker(1 * time.Second).C {
+		for range time.NewTicker(700 * time.Millisecond).C {
 			select {
 			case <-ctx.Done():
 				wg.Done()
@@ -7286,16 +7314,45 @@ func TestOCSPGatewayMissingPeerStaple(t *testing.T) {
 			}
 		}
 	}()
+
+	wg.Add(1)
+	go func() {
+		for range time.NewTicker(800 * time.Millisecond).C {
+			select {
+			case <-ctx.Done():
+				wg.Done()
+				return
+			default:
+			}
+			if err := srvB.Reload(); err != nil {
+				t.Fatal(err)
+			}
+		}
+	}()
+
 	wg.Add(1)
+	go func() {
+		for range time.NewTicker(900 * time.Millisecond).C {
+			select {
+			case <-ctx.Done():
+				wg.Done()
+				return
+			default:
+			}
+			if err := srvA.Reload(); err != nil {
+				t.Fatal(err)
+			}
+		}
+	}()
 
 	select {
 	case <-ctx.Done():
 	case msg := <-lA.ch:
-		t.Fatalf("Got OCSP Staple error: %v", msg)
+		t.Fatalf("Server A: Got OCSP Staple error: %v", msg)
 	case msg := <-lB.ch:
-		t.Fatalf("Got OCSP Staple error: %v", msg)
+		t.Fatalf("Server B: Got OCSP Staple error: %v", msg)
 	case msg := <-lC.ch:
-		t.Fatalf("Got OCSP Staple error: %v", msg)
+		t.Fatalf("Server C: Got OCSP Staple error: %v", msg)
 	}
 	wg.Wait()
 }