diff --git a/mcp-core/src/main/java/io/modelcontextprotocol/spec/DefaultMcpTransportSession.java b/mcp-core/src/main/java/io/modelcontextprotocol/spec/DefaultMcpTransportSession.java
index fdb7bfd89..6c2930abb 100644
--- a/mcp-core/src/main/java/io/modelcontextprotocol/spec/DefaultMcpTransportSession.java
+++ b/mcp-core/src/main/java/io/modelcontextprotocol/spec/DefaultMcpTransportSession.java
@@ -77,8 +77,9 @@ public void close() {
 
 	@Override
 	public Mono<Void> closeGracefully() {
-		return Mono.from(this.onClose.apply(this.sessionId.get()))
-			.then(Mono.fromRunnable(this.openConnections::dispose));
+		return Mono.defer(() -> Mono.from(this.onClose.apply(this.sessionId.get())))
+			.doFinally(signalType -> this.openConnections.dispose())
+			.then();
 	}
 
 }
diff --git a/mcp-core/src/test/java/io/modelcontextprotocol/spec/DefaultMcpTransportSessionTests.java b/mcp-core/src/test/java/io/modelcontextprotocol/spec/DefaultMcpTransportSessionTests.java
new file mode 100644
index 000000000..0da3ae70c
--- /dev/null
+++ b/mcp-core/src/test/java/io/modelcontextprotocol/spec/DefaultMcpTransportSessionTests.java
@@ -0,0 +1,56 @@
+/*
+ * Copyright 2024-2025 the original author or authors.
+ */
+
+package io.modelcontextprotocol.spec;
+
+import java.util.concurrent.atomic.AtomicBoolean;
+
+import org.junit.jupiter.api.Test;
+import reactor.core.Disposable;
+import reactor.core.publisher.Mono;
+import reactor.test.StepVerifier;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+/**
+ * Tests for {@link DefaultMcpTransportSession}.
+ */
+class DefaultMcpTransportSessionTests {
+
+	@Test
+	void shouldDisposeConnectionsEvenIfOnCloseErrors() {
+		// Given
+		AtomicBoolean disposed = new AtomicBoolean(false);
+		Disposable connection = () -> disposed.set(true);
+
+		DefaultMcpTransportSession session = new DefaultMcpTransportSession(
+				sessionId -> Mono.error(new RuntimeException("onClose failure")));
+		session.addConnection(connection);
+
+		// When
+		StepVerifier.create(session.closeGracefully())
+			.expectErrorMatches(t -> t instanceof RuntimeException && "onClose failure".equals(t.getMessage()))
+			.verify();
+
+		// Then
+		assertThat(disposed.get()).as("Connection should be disposed even if onClose fails").isTrue();
+	}
+
+	@Test
+	void shouldDisposeConnectionsOnSuccessfulClose() {
+		// Given
+		AtomicBoolean disposed = new AtomicBoolean(false);
+		Disposable connection = () -> disposed.set(true);
+
+		DefaultMcpTransportSession session = new DefaultMcpTransportSession(sessionId -> Mono.empty());
+		session.addConnection(connection);
+
+		// When
+		StepVerifier.create(session.closeGracefully()).verifyComplete();
+
+		// Then
+		assertThat(disposed.get()).as("Connection should be disposed on successful close").isTrue();
+	}
+
+}