diff --git a/spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/security/oauth2/server/servlet/OAuth2AuthorizationServerWebSecurityConfiguration.java b/spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/security/oauth2/server/servlet/OAuth2AuthorizationServerWebSecurityConfiguration.java
index c3e60f807e..5c36f2b462 100644
--- a/spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/security/oauth2/server/servlet/OAuth2AuthorizationServerWebSecurityConfiguration.java
+++ b/spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/security/oauth2/server/servlet/OAuth2AuthorizationServerWebSecurityConfiguration.java
@@ -16,6 +16,8 @@
 
 package org.springframework.boot.autoconfigure.security.oauth2.server.servlet;
 
+import java.util.Set;
+
 import org.springframework.boot.autoconfigure.condition.ConditionalOnBean;
 import org.springframework.boot.autoconfigure.security.ConditionalOnDefaultWebSecurity;
 import org.springframework.boot.autoconfigure.security.SecurityProperties;
@@ -23,6 +25,7 @@ import org.springframework.context.annotation.Bean;
 import org.springframework.context.annotation.Configuration;
 import org.springframework.core.Ordered;
 import org.springframework.core.annotation.Order;
+import org.springframework.http.MediaType;
 import org.springframework.security.config.annotation.web.builders.HttpSecurity;
 import org.springframework.security.oauth2.server.authorization.client.RegisteredClientRepository;
 import org.springframework.security.oauth2.server.authorization.config.annotation.web.configuration.OAuth2AuthorizationServerConfiguration;
@@ -30,6 +33,8 @@ import org.springframework.security.oauth2.server.authorization.config.annotatio
 import org.springframework.security.oauth2.server.authorization.settings.AuthorizationServerSettings;
 import org.springframework.security.web.SecurityFilterChain;
 import org.springframework.security.web.authentication.LoginUrlAuthenticationEntryPoint;
+import org.springframework.security.web.util.matcher.MediaTypeRequestMatcher;
+import org.springframework.security.web.util.matcher.RequestMatcher;
 
 import static org.springframework.security.config.Customizer.withDefaults;
 
@@ -49,8 +54,8 @@ class OAuth2AuthorizationServerWebSecurityConfiguration {
 		OAuth2AuthorizationServerConfiguration.applyDefaultSecurity(http);
 		http.getConfigurer(OAuth2AuthorizationServerConfigurer.class).oidc(withDefaults());
 		http.oauth2ResourceServer((resourceServer) -> resourceServer.jwt(withDefaults()));
-		http.exceptionHandling(
-				(exceptions) -> exceptions.authenticationEntryPoint(new LoginUrlAuthenticationEntryPoint("/login")));
+		http.exceptionHandling((exceptions) -> exceptions.defaultAuthenticationEntryPointFor(
+				new LoginUrlAuthenticationEntryPoint("/login"), createRequestMatcher()));
 		return http.build();
 	}
 
@@ -61,4 +66,10 @@ class OAuth2AuthorizationServerWebSecurityConfiguration {
 		return http.build();
 	}
 
+	private static RequestMatcher createRequestMatcher() {
+		MediaTypeRequestMatcher requestMatcher = new MediaTypeRequestMatcher(MediaType.TEXT_HTML);
+		requestMatcher.setIgnoredMediaTypes(Set.of(MediaType.ALL));
+		return requestMatcher;
+	}
+
 }
diff --git a/spring-boot-tests/spring-boot-smoke-tests/spring-boot-smoke-test-oauth2-authorization-server/src/test/java/smoketest/oauth2/server/SampleOAuth2AuthorizationServerApplicationTests.java b/spring-boot-tests/spring-boot-smoke-tests/spring-boot-smoke-test-oauth2-authorization-server/src/test/java/smoketest/oauth2/server/SampleOAuth2AuthorizationServerApplicationTests.java
index ce2d7b75f0..0ecf890c9f 100644
--- a/spring-boot-tests/spring-boot-smoke-tests/spring-boot-smoke-test-oauth2-authorization-server/src/test/java/smoketest/oauth2/server/SampleOAuth2AuthorizationServerApplicationTests.java
+++ b/spring-boot-tests/spring-boot-smoke-tests/spring-boot-smoke-test-oauth2-authorization-server/src/test/java/smoketest/oauth2/server/SampleOAuth2AuthorizationServerApplicationTests.java
@@ -17,6 +17,7 @@
 package smoketest.oauth2.server;
 
 import java.net.URI;
+import java.util.List;
 import java.util.Map;
 import java.util.Objects;
 
@@ -31,6 +32,7 @@ import org.springframework.http.HttpEntity;
 import org.springframework.http.HttpHeaders;
 import org.springframework.http.HttpMethod;
 import org.springframework.http.HttpStatus;
+import org.springframework.http.MediaType;
 import org.springframework.http.ResponseEntity;
 import org.springframework.security.oauth2.core.AuthorizationGrantType;
 import org.springframework.security.oauth2.core.OAuth2AccessToken;
@@ -118,4 +120,49 @@ class SampleOAuth2AuthorizationServerApplicationTests {
 			.isEqualTo(OAuth2AccessToken.TokenType.BEARER.getValue());
 	}
 
+	@Test
+	void anonymousTokenRequestShouldReturnUnauthorized() {
+		HttpHeaders headers = new HttpHeaders();
+		HttpEntity<Object> request = new HttpEntity<>(headers);
+		String requestUri = UriComponentsBuilder.fromUriString("/token")
+			.queryParam(OAuth2ParameterNames.CLIENT_ID, "messaging-client")
+			.queryParam(OAuth2ParameterNames.GRANT_TYPE, AuthorizationGrantType.CLIENT_CREDENTIALS.getValue())
+			.queryParam(OAuth2ParameterNames.SCOPE, "message.read+message.write")
+			.toUriString();
+		ResponseEntity<Map<String, Object>> entity = this.restTemplate.exchange(requestUri, HttpMethod.POST, request,
+				MAP_TYPE_REFERENCE);
+		assertThat(entity.getStatusCode()).isEqualTo(HttpStatus.UNAUTHORIZED);
+	}
+
+	@Test
+	void anonymousTokenRequestWithAcceptHeaderAllShouldReturnUnauthorized() {
+		HttpHeaders headers = new HttpHeaders();
+		headers.setAccept(List.of(MediaType.ALL));
+		HttpEntity<Object> request = new HttpEntity<>(headers);
+		String requestUri = UriComponentsBuilder.fromUriString("/token")
+			.queryParam(OAuth2ParameterNames.CLIENT_ID, "messaging-client")
+			.queryParam(OAuth2ParameterNames.GRANT_TYPE, AuthorizationGrantType.CLIENT_CREDENTIALS.getValue())
+			.queryParam(OAuth2ParameterNames.SCOPE, "message.read+message.write")
+			.toUriString();
+		ResponseEntity<Map<String, Object>> entity = this.restTemplate.exchange(requestUri, HttpMethod.POST, request,
+				MAP_TYPE_REFERENCE);
+		assertThat(entity.getStatusCode()).isEqualTo(HttpStatus.UNAUTHORIZED);
+	}
+
+	@Test
+	void anonymousTokenRequestWithAcceptHeaderTextHtmlShouldRedirectToLogin() {
+		HttpHeaders headers = new HttpHeaders();
+		headers.setAccept(List.of(MediaType.TEXT_HTML));
+		HttpEntity<Object> request = new HttpEntity<>(headers);
+		String requestUri = UriComponentsBuilder.fromUriString("/token")
+			.queryParam(OAuth2ParameterNames.CLIENT_ID, "messaging-client")
+			.queryParam(OAuth2ParameterNames.GRANT_TYPE, AuthorizationGrantType.CLIENT_CREDENTIALS.getValue())
+			.queryParam(OAuth2ParameterNames.SCOPE, "message.read+message.write")
+			.toUriString();
+		ResponseEntity<Map<String, Object>> entity = this.restTemplate.exchange(requestUri, HttpMethod.POST, request,
+				MAP_TYPE_REFERENCE);
+		assertThat(entity.getStatusCode()).isEqualTo(HttpStatus.FOUND);
+		assertThat(entity.getHeaders().getLocation()).isEqualTo(URI.create("http://localhost:" + this.port + "/login"));
+	}
+
 }