diff --git a/spring-cloud-netflix-eureka-client/src/main/java/org/springframework/cloud/netflix/eureka/http/RestTemplateTransportClientFactory.java b/spring-cloud-netflix-eureka-client/src/main/java/org/springframework/cloud/netflix/eureka/http/RestTemplateTransportClientFactory.java
index 9c15ecfe7..3c0f3f54f 100644
--- a/spring-cloud-netflix-eureka-client/src/main/java/org/springframework/cloud/netflix/eureka/http/RestTemplateTransportClientFactory.java
+++ b/spring-cloud-netflix-eureka-client/src/main/java/org/springframework/cloud/netflix/eureka/http/RestTemplateTransportClientFactory.java
@@ -122,7 +122,11 @@ public class RestTemplateTransportClientFactory implements TransportClientFactor
 		RestTemplate restTemplate;
 
 		if (restTemplateBuilderSupplier != null && restTemplateBuilderSupplier.get() != null) {
-			restTemplate = restTemplateBuilderSupplier.get().requestFactory(() -> requestFactory).build();
+			// Avoid using RestTemplateBuilder.requestFactory(() -> requestFactory)
+			// when we have a concrete type, the reflective builder can throw errors if
+			// there is custom configuration (ie Redirects.DONT_FOLLOW) gh-4423
+			restTemplate = restTemplateBuilderSupplier.get().build();
+			restTemplate.setRequestFactory(requestFactory);
 		}
 		else {
 			restTemplate = new RestTemplate(requestFactory);
diff --git a/spring-cloud-netflix-eureka-client/src/test/java/org/springframework/cloud/netflix/eureka/http/RestTemplateTransportClientFactoryTests.java b/spring-cloud-netflix-eureka-client/src/test/java/org/springframework/cloud/netflix/eureka/http/RestTemplateTransportClientFactoryTests.java
index 37aa572c3..dbad69d55 100644
--- a/spring-cloud-netflix-eureka-client/src/test/java/org/springframework/cloud/netflix/eureka/http/RestTemplateTransportClientFactoryTests.java
+++ b/spring-cloud-netflix-eureka-client/src/test/java/org/springframework/cloud/netflix/eureka/http/RestTemplateTransportClientFactoryTests.java
@@ -16,12 +16,22 @@
 
 package org.springframework.cloud.netflix.eureka.http;
 
+import java.util.Optional;
+
 import com.netflix.discovery.shared.resolver.DefaultEndpoint;
 import com.netflix.discovery.shared.transport.EurekaHttpClient;
 import org.junit.jupiter.api.AfterEach;
 import org.junit.jupiter.api.BeforeEach;
 import org.junit.jupiter.api.Test;
 
+import org.springframework.boot.http.client.ClientHttpRequestFactorySettings;
+import org.springframework.boot.http.client.ClientHttpRequestFactorySettings.Redirects;
+import org.springframework.boot.web.client.RestTemplateBuilder;
+import org.springframework.http.client.ClientHttpRequestFactory;
+import org.springframework.http.client.HttpComponentsClientHttpRequestFactory;
+import org.springframework.http.client.InterceptingClientHttpRequestFactory;
+import org.springframework.web.client.RestTemplate;
+
 import static org.assertj.core.api.Assertions.assertThat;
 
 /**
@@ -58,6 +68,24 @@ class RestTemplateTransportClientFactoryTests {
 		assertThat(eurekaHttpClient).isInstanceOf(RestTemplateEurekaHttpClient.class);
 	}
 
+	@Test
+	void testRequestFactorySetWithRestTemplateBuilderSupplier() {
+		// Gateway Server WebMVC sets Redirects.DONT_FOLLOW, gh-4423
+		RestTemplateBuilder builder = new RestTemplateBuilder()
+			.requestFactorySettings(new ClientHttpRequestFactorySettings(Redirects.DONT_FOLLOW, null, null, null));
+		transportClientFactory = new RestTemplateTransportClientFactory(Optional.empty(), Optional.empty(),
+				new DefaultEurekaClientHttpRequestFactorySupplier(), () -> builder);
+		EurekaHttpClient eurekaHttpClient = transportClientFactory
+			.newClient(new DefaultEndpoint("http://localhost:8761"));
+		RestTemplateEurekaHttpClient restTemplateEurekaHttpClient = (RestTemplateEurekaHttpClient) eurekaHttpClient;
+		RestTemplate restTemplate = restTemplateEurekaHttpClient.getRestTemplate();
+		ClientHttpRequestFactory requestFactory = restTemplate.getRequestFactory();
+		if (requestFactory instanceof InterceptingClientHttpRequestFactory interceptingClientHttpRequestFactory) {
+			requestFactory = interceptingClientHttpRequestFactory.getDelegate();
+		}
+		assertThat(requestFactory).isInstanceOf(HttpComponentsClientHttpRequestFactory.class);
+	}
+
 	@AfterEach
 	void shutdown() {
 		transportClientFactory.shutdown();