diff --git a/spring-boot-project/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/security/oauth2/resource/reactive/ReactiveOAuth2ResourceServerAutoConfigurationTests.java b/spring-boot-project/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/security/oauth2/resource/reactive/ReactiveOAuth2ResourceServerAutoConfigurationTests.java
index addbf73fc9..2769b7e4e0 100644
--- a/spring-boot-project/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/security/oauth2/resource/reactive/ReactiveOAuth2ResourceServerAutoConfigurationTests.java
+++ b/spring-boot-project/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/security/oauth2/resource/reactive/ReactiveOAuth2ResourceServerAutoConfigurationTests.java
@@ -81,6 +81,12 @@ class ReactiveOAuth2ResourceServerAutoConfigurationTests {
 
 	private MockWebServer server;
 
+	private static final String JWK_SET = "{\"keys\":[{\"kty\":\"RSA\",\"e\":\"AQAB\",\"use\":\"sig\"," +
+			"\"kid\":\"one\",\"n\":\"oXJ8OyOv_eRnce4akdanR4KYRfnC2zLV4uYNQpcFn6oHL0dj7D6kxQmsXoYgJV8ZVDn71KGm" +
+			"uLvolxsDncc2UrhyMBY6DVQVgMSVYaPCTgW76iYEKGgzTEw5IBRQL9w3SRJWd3VJTZZQjkXef48Ocz06PGF3lhbz4t5UEZtd" +
+			"F4rIe7u-977QwHuh7yRPBQ3sII-cVoOUMgaXB9SHcGF2iZCtPzL_IffDUcfhLQteGebhW8A6eUHgpD5A1PQ-JCw_G7UOzZAj" +
+			"jDjtNM2eqm8j-Ms_gqnm4MiCZ4E-9pDN77CAAPVN7kuX6ejs9KBXpk01z48i9fORYk9u7rAkh1HuQw\"}]}";
+
 	@AfterEach
 	void cleanup() throws Exception {
 		if (this.server != null) {
@@ -137,7 +143,8 @@ class ReactiveOAuth2ResourceServerAutoConfigurationTests {
 					assertFilterConfiguredWithJwtAuthenticationManager(context);
 					assertThat(context.containsBean("jwtDecoderByIssuerUri")).isTrue();
 				});
-		assertThat(this.server.getRequestCount()).isEqualTo(1);
+		// The last request is to the JWK Set endpoint to look up the algorithm
+		assertThat(this.server.getRequestCount()).isEqualTo(2);
 	}
 
 	@Test
@@ -153,7 +160,8 @@ class ReactiveOAuth2ResourceServerAutoConfigurationTests {
 					assertFilterConfiguredWithJwtAuthenticationManager(context);
 					assertThat(context.containsBean("jwtDecoderByIssuerUri")).isTrue();
 				});
-		assertThat(this.server.getRequestCount()).isEqualTo(2);
+		// The last request is to the JWK Set endpoint to look up the algorithm
+		assertThat(this.server.getRequestCount()).isEqualTo(3);
 	}
 
 	@Test
@@ -169,7 +177,8 @@ class ReactiveOAuth2ResourceServerAutoConfigurationTests {
 					assertFilterConfiguredWithJwtAuthenticationManager(context);
 					assertThat(context.containsBean("jwtDecoderByIssuerUri")).isTrue();
 				});
-		assertThat(this.server.getRequestCount()).isEqualTo(3);
+		// The last request is to the JWK Set endpoint to look up the algorithm
+		assertThat(this.server.getRequestCount()).isEqualTo(4);
 	}
 
 	@Test
@@ -396,6 +405,8 @@ class ReactiveOAuth2ResourceServerAutoConfigurationTests {
 				.setBody(new ObjectMapper().writeValueAsString(getResponse(issuer)))
 				.setHeader(HttpHeaders.CONTENT_TYPE, MediaType.APPLICATION_JSON_VALUE);
 		this.server.enqueue(mockResponse);
+		this.server.enqueue(
+				new MockResponse().setResponseCode(200).setHeader("Content-Type", "application/json").setBody(JWK_SET));
 	}
 
 	private void setupMockResponsesWithErrors(String issuer, int errorResponseCount) throws JsonProcessingException {
@@ -413,7 +424,7 @@ class ReactiveOAuth2ResourceServerAutoConfigurationTests {
 		response.put("code_challenge_methods_supported", Collections.emptyList());
 		response.put("id_token_signing_alg_values_supported", Collections.emptyList());
 		response.put("issuer", issuer);
-		response.put("jwks_uri", "https://example.com/oauth2/v3/certs");
+		response.put("jwks_uri", issuer + "/.well-known/jwks.json");
 		response.put("response_types_supported", Collections.emptyList());
 		response.put("revocation_endpoint", "https://example.com/o/oauth2/revoke");
 		response.put("scopes_supported", Collections.singletonList("openid"));
diff --git a/spring-boot-project/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/security/oauth2/resource/servlet/OAuth2ResourceServerAutoConfigurationTests.java b/spring-boot-project/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/security/oauth2/resource/servlet/OAuth2ResourceServerAutoConfigurationTests.java
index 91b207cc17..dc4f7cc214 100644
--- a/spring-boot-project/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/security/oauth2/resource/servlet/OAuth2ResourceServerAutoConfigurationTests.java
+++ b/spring-boot-project/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/security/oauth2/resource/servlet/OAuth2ResourceServerAutoConfigurationTests.java
@@ -75,6 +75,12 @@ class OAuth2ResourceServerAutoConfigurationTests {
 
 	private MockWebServer server;
 
+	private static final String JWK_SET = "{\"keys\":[{\"kty\":\"RSA\",\"e\":\"AQAB\",\"use\":\"sig\"," +
+			"\"kid\":\"one\",\"n\":\"oXJ8OyOv_eRnce4akdanR4KYRfnC2zLV4uYNQpcFn6oHL0dj7D6kxQmsXoYgJV8ZVDn71KGm" +
+			"uLvolxsDncc2UrhyMBY6DVQVgMSVYaPCTgW76iYEKGgzTEw5IBRQL9w3SRJWd3VJTZZQjkXef48Ocz06PGF3lhbz4t5UEZtd" +
+			"F4rIe7u-977QwHuh7yRPBQ3sII-cVoOUMgaXB9SHcGF2iZCtPzL_IffDUcfhLQteGebhW8A6eUHgpD5A1PQ-JCw_G7UOzZAj" +
+			"jDjtNM2eqm8j-Ms_gqnm4MiCZ4E-9pDN77CAAPVN7kuX6ejs9KBXpk01z48i9fORYk9u7rAkh1HuQw\"}]}";
+
 	@AfterEach
 	void cleanup() throws Exception {
 		if (this.server != null) {
@@ -133,7 +139,8 @@ class OAuth2ResourceServerAutoConfigurationTests {
 					assertThat(context).hasSingleBean(JwtDecoder.class);
 					assertThat(context.containsBean("jwtDecoderByIssuerUri")).isTrue();
 				});
-		assertThat(this.server.getRequestCount()).isEqualTo(1);
+		// The last request is to the JWK Set endpoint to look up the algorithm
+		assertThat(this.server.getRequestCount()).isEqualTo(2);
 	}
 
 	@Test
@@ -149,7 +156,8 @@ class OAuth2ResourceServerAutoConfigurationTests {
 					assertThat(context).hasSingleBean(JwtDecoder.class);
 					assertThat(context.containsBean("jwtDecoderByIssuerUri")).isTrue();
 				});
-		assertThat(this.server.getRequestCount()).isEqualTo(2);
+		// The last request is to the JWK Set endpoint to look up the algorithm
+		assertThat(this.server.getRequestCount()).isEqualTo(3);
 	}
 
 	@Test
@@ -165,7 +173,8 @@ class OAuth2ResourceServerAutoConfigurationTests {
 					assertThat(context).hasSingleBean(JwtDecoder.class);
 					assertThat(context.containsBean("jwtDecoderByIssuerUri")).isTrue();
 				});
-		assertThat(this.server.getRequestCount()).isEqualTo(3);
+		// The last request is to the JWK Set endpoint to look up the algorithm
+		assertThat(this.server.getRequestCount()).isEqualTo(4);
 	}
 
 	@Test
@@ -414,6 +423,8 @@ class OAuth2ResourceServerAutoConfigurationTests {
 				.setBody(new ObjectMapper().writeValueAsString(getResponse(issuer)))
 				.setHeader(HttpHeaders.CONTENT_TYPE, MediaType.APPLICATION_JSON_VALUE);
 		this.server.enqueue(mockResponse);
+		this.server.enqueue(
+				new MockResponse().setResponseCode(200).setHeader("Content-Type", "application/json").setBody(JWK_SET));
 	}
 
 	private void setupMockResponsesWithErrors(String issuer, int errorResponseCount) throws JsonProcessingException {
@@ -431,7 +442,7 @@ class OAuth2ResourceServerAutoConfigurationTests {
 		response.put("code_challenge_methods_supported", Collections.emptyList());
 		response.put("id_token_signing_alg_values_supported", Collections.emptyList());
 		response.put("issuer", issuer);
-		response.put("jwks_uri", "https://example.com/oauth2/v3/certs");
+		response.put("jwks_uri", issuer + "/.well-known/jwks.json");
 		response.put("response_types_supported", Collections.emptyList());
 		response.put("revocation_endpoint", "https://example.com/o/oauth2/revoke");
 		response.put("scopes_supported", Collections.singletonList("openid"));
diff --git a/spring-boot-project/spring-boot-dependencies/build.gradle b/spring-boot-project/spring-boot-dependencies/build.gradle
index f90b89c523..59fec09af9 100644
--- a/spring-boot-project/spring-boot-dependencies/build.gradle
+++ b/spring-boot-project/spring-boot-dependencies/build.gradle
@@ -1618,7 +1618,7 @@ bom {
 			]
 		}
 	}
-	library("Spring Security", "5.4.2") {
+	library("Spring Security", "5.5.0-M1") {
 		group("org.springframework.security") {
 			imports = [
 				"spring-security-bom"