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 c2f415378b..f6ca3e5f66 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;
@@ -170,7 +171,7 @@ public final class JwtIssuerReactiveAuthenticationManagerResolver
 							new JwtReactiveAuthenticationManager(ReactiveJwtDecoders.fromIssuerLocation(k))
 					)
 					.subscribeOn(Schedulers.boundedElastic())
-					.cache());
+					.cache((manager) -> Duration.ofMillis(Long.MAX_VALUE), (ex) -> Duration.ZERO, () -> Duration.ZERO));
 		}
 	}
 }
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 21df5189fe..e4d8e6d34d 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
@@ -38,9 +38,11 @@ import org.springframework.security.authentication.AuthenticationManager;
 import org.springframework.security.authentication.AuthenticationManagerResolver;
 import org.springframework.security.oauth2.core.OAuth2AuthenticationException;
 import org.springframework.security.oauth2.jose.TestKeys;
+import org.springframework.security.oauth2.jwt.JwtClaimNames;
 
 import static org.assertj.core.api.Assertions.assertThat;
 import static org.assertj.core.api.Assertions.assertThatCode;
+import static org.assertj.core.api.Assertions.assertThatExceptionOfType;
 import static org.mockito.Mockito.mock;
 import static org.springframework.security.oauth2.jwt.JwtClaimNames.ISS;
 
@@ -85,6 +87,35 @@ public class JwtIssuerAuthenticationManagerResolverTests {
 		}
 	}
 
+	@Test
+	public void resolveWhenIssuerFailsThenErrorNotCached() 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))
+			);
+			// @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);
+			MockHttpServletRequest request = new MockHttpServletRequest();
+			request.addHeader("Authorization", "Bearer " + jws.serialize());
+			assertThatExceptionOfType(IllegalArgumentException.class)
+					.isThrownBy(() -> authenticationManagerResolver.resolve(request));
+			AuthenticationManager authenticationManager = authenticationManagerResolver.resolve(request);
+			assertThat(authenticationManager).isNotNull();
+		}
+	}
+
 	@Test
 	public void resolveWhenUsingUntrustedIssuerThenException() {
 		JwtIssuerAuthenticationManagerResolver authenticationManagerResolver =
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 d694707096..4c1a4b176f 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
@@ -40,9 +40,11 @@ import org.springframework.security.authentication.ReactiveAuthenticationManager
 import org.springframework.security.authentication.ReactiveAuthenticationManagerResolver;
 import org.springframework.security.oauth2.core.OAuth2AuthenticationException;
 import org.springframework.security.oauth2.jose.TestKeys;
+import org.springframework.security.oauth2.jwt.JwtClaimNames;
 
 import static org.assertj.core.api.Assertions.assertThat;
 import static org.assertj.core.api.Assertions.assertThatCode;
+import static org.assertj.core.api.Assertions.assertThatExceptionOfType;
 import static org.mockito.Mockito.mock;
 import static org.springframework.security.oauth2.jwt.JwtClaimNames.ISS;
 
@@ -85,6 +87,31 @@ public class JwtIssuerReactiveAuthenticationManagerResolverTests {
 		}
 	}
 
+	// gh-10444
+	@Test
+	public void resolveWhenIssuerFailsThenErrorNotCached() 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)));
+			// @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);
+			MockServerWebExchange exchange = withBearerToken(jws.serialize());
+			assertThatExceptionOfType(IllegalArgumentException.class)
+					.isThrownBy(() -> authenticationManagerResolver.resolve(exchange).block());
+			ReactiveAuthenticationManager authenticationManager = authenticationManagerResolver.resolve(exchange)
+					.block();
+			assertThat(authenticationManager).isNotNull();
+		}
+	}
+
 	@Test
 	public void resolveWhenUsingUntrustedIssuerThenException() {
 		JwtIssuerReactiveAuthenticationManagerResolver authenticationManagerResolver =