diff --git a/oauth2/oauth2-jose/src/main/java/org/springframework/security/oauth2/jwt/ReactiveRemoteJWKSource.java b/oauth2/oauth2-jose/src/main/java/org/springframework/security/oauth2/jwt/ReactiveRemoteJWKSource.java
index e976328623..48f491ccad 100644
--- a/oauth2/oauth2-jose/src/main/java/org/springframework/security/oauth2/jwt/ReactiveRemoteJWKSource.java
+++ b/oauth2/oauth2-jose/src/main/java/org/springframework/security/oauth2/jwt/ReactiveRemoteJWKSource.java
@@ -19,6 +19,7 @@
 import java.text.ParseException;
 import java.util.Collections;
 import java.util.List;
+import java.util.Objects;
 import java.util.Set;
 import java.util.concurrent.atomic.AtomicReference;
 
@@ -44,6 +45,12 @@ class ReactiveRemoteJWKSource implements ReactiveJWKSource {
 	 */
 	private final AtomicReference<Mono<JWKSet>> cachedJWKSet = new AtomicReference<>(Mono.empty());
 
+	/**
+	 * In-flight JWK set fetch request, used to coalesce concurrent fetches into a single
+	 * HTTP call.
+	 */
+	private final AtomicReference<@Nullable Mono<JWKSet>> inflightRequest = new AtomicReference<>();
+
 	/**
 	 * The cached JWK set URL.
 	 */
@@ -101,24 +108,23 @@ private Mono<List<JWK>> get(JWKSelector jwkSelector, JWKSet jwkSet) {
 	}
 
 	/**
-	 * Updates the cached JWK set from the configured URL.
+	 * Updates the cached JWK set from the configured URL. Concurrent calls are coalesced
+	 * into a single HTTP request to prevent thundering herd during cold start.
 	 * @return The updated JWK set.
 	 * @throws RemoteKeySourceException If JWK retrieval failed.
 	 */
 	private Mono<JWKSet> getJWKSet() {
-		// @formatter:off
-		return this.jwkSetUrlProvider
-				.flatMap((jwkSetURL) -> this.webClient.get()
-					.uri(jwkSetURL)
-					.retrieve()
-					.bodyToMono(String.class)
-				)
-				.map(this::parse)
-				.doOnNext((jwkSet) -> this.cachedJWKSet
-					.set(Mono.just(jwkSet))
-				)
-				.cache();
-		// @formatter:on
+		Mono<JWKSet> fetch = Mono.defer(() -> this.jwkSetUrlProvider
+			.flatMap((jwkSetURL) -> this.webClient.get().uri(jwkSetURL).retrieve().bodyToMono(String.class))
+			.map(this::parse)
+			.doOnNext((jwkSet) -> {
+				this.cachedJWKSet.set(Mono.just(jwkSet));
+				this.inflightRequest.set(null);
+			})
+			.doOnError((ex) -> this.inflightRequest.set(null))
+			.doOnCancel(() -> this.inflightRequest.set(null))
+			.switchIfEmpty(Mono.fromRunnable(() -> this.inflightRequest.set(null)))).cache();
+		return Objects.requireNonNull(this.inflightRequest.updateAndGet((v) -> (v != null) ? v : fetch));
 	}
 
 	private JWKSet parse(String body) {
diff --git a/oauth2/oauth2-jose/src/test/java/org/springframework/security/oauth2/jwt/ReactiveRemoteJWKSourceTests.java b/oauth2/oauth2-jose/src/test/java/org/springframework/security/oauth2/jwt/ReactiveRemoteJWKSourceTests.java
index e00b76047f..719f8ae900 100644
--- a/oauth2/oauth2-jose/src/test/java/org/springframework/security/oauth2/jwt/ReactiveRemoteJWKSourceTests.java
+++ b/oauth2/oauth2-jose/src/test/java/org/springframework/security/oauth2/jwt/ReactiveRemoteJWKSourceTests.java
@@ -16,8 +16,10 @@
 
 package org.springframework.security.oauth2.jwt;
 
+import java.time.Duration;
 import java.util.Collections;
 import java.util.List;
+import java.util.concurrent.TimeUnit;
 import java.util.function.Supplier;
 
 import com.nimbusds.jose.jwk.JWK;
@@ -32,7 +34,9 @@
 import org.junit.jupiter.api.extension.ExtendWith;
 import org.mockito.Mock;
 import org.mockito.junit.jupiter.MockitoExtension;
+import reactor.core.publisher.Flux;
 import reactor.core.publisher.Mono;
+import reactor.core.scheduler.Schedulers;
 
 import org.springframework.web.reactive.function.client.WebClientResponseException;
 
@@ -166,6 +170,44 @@ public void getWhenNoMatchAndKeyIdMatchThenEmpty() {
 		assertThat(this.source.get(this.selector).block()).isEmpty();
 	}
 
+	@Test
+	public void getWhenConcurrentRequestsThenSingleFetch() {
+		// given
+		given(this.matcher.matches(any())).willReturn(true);
+		int concurrentRequests = 10;
+		for (int i = 0; i < concurrentRequests; i++) {
+			this.server.enqueue(new MockResponse().setBody(this.keys).setBodyDelay(100, TimeUnit.MILLISECONDS));
+		}
+
+		// when
+		List<List<JWK>> results = Flux.range(0, concurrentRequests)
+			.flatMap((i) -> this.source.get(this.selector).subscribeOn(Schedulers.parallel()), concurrentRequests)
+			.collectList()
+			.block(Duration.ofSeconds(5));
+
+		// then
+		assertThat(results).hasSize(concurrentRequests);
+		assertThat(this.server.getRequestCount()).isEqualTo(1);
+	}
+
+	@Test
+	public void getWhenEmptyResponseThenNextCallSucceeds() {
+		// given
+		given(this.matcher.matches(any())).willReturn(true);
+		this.source = new ReactiveRemoteJWKSource(Mono.fromSupplier(this.mockStringSupplier));
+		// first call: supplier returns null URL, causing empty Mono from
+		// jwkSetUrlProvider
+		willReturn(null).given(this.mockStringSupplier).get();
+
+		// when: first call completes empty
+		List<JWK> firstResult = this.source.get(this.selector).block(Duration.ofSeconds(5));
+
+		// then: inflight is cleared and second call can succeed
+		willReturn(this.server.url("/").toString()).given(this.mockStringSupplier).get();
+		List<JWK> secondResult = this.source.get(this.selector).block(Duration.ofSeconds(5));
+		assertThat(secondResult).isNotEmpty();
+	}
+
 	@Test
 	public void getShouldRecoverAndReturnKeysAfterErrorCase() {
 		given(this.matcher.matches(any())).willReturn(true);