diff --git a/oauth2/oauth2-resource-server/src/main/java/org/springframework/security/oauth2/server/resource/authentication/JwtIssuerReactiveAuthenticationManagerResolver.java b/oauth2/oauth2-resource-server/src/main/java/org/springframework/security/oauth2/server/resource/authentication/JwtIssuerReactiveAuthenticationManagerResolver.java
index afbfb38f9c..26aeca6d08 100644
--- a/oauth2/oauth2-resource-server/src/main/java/org/springframework/security/oauth2/server/resource/authentication/JwtIssuerReactiveAuthenticationManagerResolver.java
+++ b/oauth2/oauth2-resource-server/src/main/java/org/springframework/security/oauth2/server/resource/authentication/JwtIssuerReactiveAuthenticationManagerResolver.java
@@ -16,6 +16,7 @@
 
 package org.springframework.security.oauth2.server.resource.authentication;
 
+import java.time.Duration;
 import java.util.ArrayList;
 import java.util.Arrays;
 import java.util.Collection;
@@ -186,7 +187,7 @@ public final class JwtIssuerReactiveAuthenticationManagerResolver
 			return this.authenticationManagers.computeIfAbsent(issuer,
 					(k) -> Mono.<ReactiveAuthenticationManager>fromCallable(() -> new JwtReactiveAuthenticationManager(ReactiveJwtDecoders.fromIssuerLocation(k)))
 							.subscribeOn(Schedulers.boundedElastic())
-							.cache()
+							.cache((manager) -> Duration.ofMillis(Long.MAX_VALUE), (ex) -> Duration.ZERO, () -> Duration.ZERO)
 			);
 			// @formatter:on
 		}
diff --git a/oauth2/oauth2-resource-server/src/test/java/org/springframework/security/oauth2/server/resource/authentication/JwtIssuerAuthenticationManagerResolverTests.java b/oauth2/oauth2-resource-server/src/test/java/org/springframework/security/oauth2/server/resource/authentication/JwtIssuerAuthenticationManagerResolverTests.java
index 99ab3933b9..8bc9573eda 100644
--- a/oauth2/oauth2-resource-server/src/test/java/org/springframework/security/oauth2/server/resource/authentication/JwtIssuerAuthenticationManagerResolverTests.java
+++ b/oauth2/oauth2-resource-server/src/test/java/org/springframework/security/oauth2/server/resource/authentication/JwtIssuerAuthenticationManagerResolverTests.java
@@ -96,6 +96,40 @@ public class JwtIssuerAuthenticationManagerResolverTests {
 		}
 	}
 
+	@Test
+	public void resolveWhednUsingTrustedIssuerThenReturnsAuthenticationManager() throws Exception {
+		try (MockWebServer server = new MockWebServer()) {
+			server.start();
+			String issuer = server.url("").toString();
+			// @formatter:off
+			server.enqueue(new MockResponse().setResponseCode(500)
+					.setHeader("Content-Type", "application/json")
+					.setBody(String.format(DEFAULT_RESPONSE_TEMPLATE, issuer, issuer))
+			);
+			server.enqueue(new MockResponse().setResponseCode(200)
+					.setHeader("Content-Type", "application/json")
+					.setBody(String.format(DEFAULT_RESPONSE_TEMPLATE, issuer, issuer))
+			);
+			server.enqueue(new MockResponse().setResponseCode(200)
+					.setHeader("Content-Type", "application/json")
+					.setBody(JWK_SET)
+			);
+			// @formatter:on
+			JWSObject jws = new JWSObject(new JWSHeader(JWSAlgorithm.RS256),
+					new Payload(new JSONObject(Collections.singletonMap(JwtClaimNames.ISS, issuer))));
+			jws.sign(new RSASSASigner(TestKeys.DEFAULT_PRIVATE_KEY));
+			JwtIssuerAuthenticationManagerResolver authenticationManagerResolver = new JwtIssuerAuthenticationManagerResolver(
+					issuer);
+			Authentication token = withBearerToken(jws.serialize());
+			AuthenticationManager authenticationManager = authenticationManagerResolver.resolve(null);
+			assertThat(authenticationManager).isNotNull();
+			assertThatExceptionOfType(IllegalArgumentException.class)
+					.isThrownBy(() -> authenticationManager.authenticate(token));
+			Authentication authentication = authenticationManager.authenticate(token);
+			assertThat(authentication.isAuthenticated()).isTrue();
+		}
+	}
+
 	@Test
 	public void resolveWhenUsingSameIssuerThenReturnsSameAuthenticationManager() throws Exception {
 		try (MockWebServer server = new MockWebServer()) {
diff --git a/oauth2/oauth2-resource-server/src/test/java/org/springframework/security/oauth2/server/resource/authentication/JwtIssuerReactiveAuthenticationManagerResolverTests.java b/oauth2/oauth2-resource-server/src/test/java/org/springframework/security/oauth2/server/resource/authentication/JwtIssuerReactiveAuthenticationManagerResolverTests.java
index c13eac86f8..357d95423d 100644
--- a/oauth2/oauth2-resource-server/src/test/java/org/springframework/security/oauth2/server/resource/authentication/JwtIssuerReactiveAuthenticationManagerResolverTests.java
+++ b/oauth2/oauth2-resource-server/src/test/java/org/springframework/security/oauth2/server/resource/authentication/JwtIssuerReactiveAuthenticationManagerResolverTests.java
@@ -95,6 +95,34 @@ public class JwtIssuerReactiveAuthenticationManagerResolverTests {
 		}
 	}
 
+	// gh-10444
+	@Test
+	public void resolveWhednUsingTrustedIssuerThenReturnsAuthenticationManager() throws Exception {
+		try (MockWebServer server = new MockWebServer()) {
+			String issuer = server.url("").toString();
+			// @formatter:off
+			server.enqueue(new MockResponse().setResponseCode(500).setHeader("Content-Type", "application/json")
+					.setBody(String.format(DEFAULT_RESPONSE_TEMPLATE, issuer, issuer)));
+			server.enqueue(new MockResponse().setResponseCode(200).setHeader("Content-Type", "application/json")
+					.setBody(String.format(DEFAULT_RESPONSE_TEMPLATE, issuer, issuer)));
+			server.enqueue(new MockResponse().setResponseCode(200).setHeader("Content-Type", "application/json")
+					.setBody(JWK_SET));
+			// @formatter:on
+			JWSObject jws = new JWSObject(new JWSHeader(JWSAlgorithm.RS256),
+					new Payload(new JSONObject(Collections.singletonMap(JwtClaimNames.ISS, issuer))));
+			jws.sign(new RSASSASigner(TestKeys.DEFAULT_PRIVATE_KEY));
+			JwtIssuerReactiveAuthenticationManagerResolver authenticationManagerResolver = new JwtIssuerReactiveAuthenticationManagerResolver(
+					issuer);
+			ReactiveAuthenticationManager authenticationManager = authenticationManagerResolver.resolve(null).block();
+			assertThat(authenticationManager).isNotNull();
+			Authentication token = withBearerToken(jws.serialize());
+			assertThatExceptionOfType(IllegalArgumentException.class)
+					.isThrownBy(() -> authenticationManager.authenticate(token).block());
+			Authentication authentication = authenticationManager.authenticate(token).block();
+			assertThat(authentication.isAuthenticated()).isTrue();
+		}
+	}
+
 	@Test
 	public void resolveWhenUsingSameIssuerThenReturnsSameAuthenticationManager() throws Exception {
 		try (MockWebServer server = new MockWebServer()) {