diff --git a/rsocket-core/src/main/java/io/rsocket/core/ServerSetup.java b/rsocket-core/src/main/java/io/rsocket/core/ServerSetup.java
index 5aae22e89..7ca400862 100644
--- a/rsocket-core/src/main/java/io/rsocket/core/ServerSetup.java
+++ b/rsocket-core/src/main/java/io/rsocket/core/ServerSetup.java
@@ -29,6 +29,8 @@
 import io.rsocket.resume.*;
 import java.nio.channels.ClosedChannelException;
 import java.time.Duration;
+import java.util.Map;
+import java.util.concurrent.ConcurrentHashMap;
 import java.util.function.BiFunction;
 import java.util.function.Function;
 import reactor.core.publisher.Mono;
@@ -96,6 +98,8 @@ static class ResumableServerSetup extends ServerSetup {
     private final Duration resumeStreamTimeout;
     private final Function<? super ByteBuf, ? extends ResumableFramesStore> resumeStoreFactory;
     private final boolean cleanupStoreOnKeepAlive;
+    private final Map<DuplexConnection, DuplexConnection> rawConnections =
+        new ConcurrentHashMap<>();
 
     ResumableServerSetup(
         Duration timeout,
@@ -136,6 +140,8 @@ public Mono<Void> acceptRSocketSetup(
 
         sessionManager.save(serverRSocketSession, resumeToken);
 
+        rawConnections.put(resumableDuplexConnection, duplexConnection);
+
         return then.apply(
             new ResumableKeepAliveHandler(
                 resumableDuplexConnection, serverRSocketSession, serverRSocketSession),
@@ -145,6 +151,21 @@ public Mono<Void> acceptRSocketSetup(
       }
     }
 
+    @Override
+    void sendError(DuplexConnection duplexConnection, RSocketErrorException exception) {
+      DuplexConnection rawConnection = rawConnections.remove(duplexConnection);
+      if (rawConnection != null) {
+        // Send the error directly on the raw connection, bypassing ResumableDuplexConnection
+        // which would buffer the frame instead of sending it to the client
+        rawConnection.sendErrorAndClose(exception);
+        rawConnection.receive().subscribe();
+        // Dispose the resumable connection to clean up the session
+        duplexConnection.dispose();
+      } else {
+        super.sendError(duplexConnection, exception);
+      }
+    }
+
     @Override
     public Mono<Void> acceptRSocketResume(ByteBuf frame, DuplexConnection duplexConnection) {
       ServerRSocketSession session = sessionManager.get(ResumeFrameCodec.token(frame));
diff --git a/rsocket-core/src/test/java/io/rsocket/core/RSocketServerTest.java b/rsocket-core/src/test/java/io/rsocket/core/RSocketServerTest.java
index a335ac1f3..36cdf12a8 100644
--- a/rsocket-core/src/test/java/io/rsocket/core/RSocketServerTest.java
+++ b/rsocket-core/src/test/java/io/rsocket/core/RSocketServerTest.java
@@ -198,4 +198,36 @@ public void ensuresErrorFrameDeliveredPriorConnectionDisposal() {
     server.dispose();
     transport.alloc().assertHasNoLeaks();
   }
+
+  @Test
+  public void ensuresErrorFrameDeliveredWithResumeEnabled() {
+    TestServerTransport transport = new TestServerTransport();
+    Closeable server =
+        RSocketServer.create()
+            .resume(new Resume())
+            .acceptor(
+                (setup, sendingSocket) -> Mono.error(new RejectedSetupException("ACCESS_DENIED")))
+            .bind(transport)
+            .block();
+
+    TestDuplexConnection connection = transport.connect();
+    connection.addToReceivedBuffer(
+        SetupFrameCodec.encode(
+            ByteBufAllocator.DEFAULT,
+            false,
+            0,
+            1,
+            Unpooled.wrappedBuffer("test-resume-token".getBytes()),
+            "metadata_type",
+            "data_type",
+            EmptyPayload.INSTANCE));
+
+    StepVerifier.create(connection.onClose()).expectComplete().verify(Duration.ofSeconds(30));
+    FrameAssert.assertThat(connection.pollFrame())
+        .hasStreamIdZero()
+        .hasData("ACCESS_DENIED")
+        .hasNoLeaks();
+    server.dispose();
+    transport.alloc().assertHasNoLeaks();
+  }
 }