diff --git a/spring-modulith-events/spring-modulith-events-core/src/main/java/org/springframework/modulith/events/support/PersistentApplicationEventMulticaster.java b/spring-modulith-events/spring-modulith-events-core/src/main/java/org/springframework/modulith/events/support/PersistentApplicationEventMulticaster.java
index 47356b981..f4c157d10 100644
--- a/spring-modulith-events/spring-modulith-events-core/src/main/java/org/springframework/modulith/events/support/PersistentApplicationEventMulticaster.java
+++ b/spring-modulith-events/spring-modulith-events-core/src/main/java/org/springframework/modulith/events/support/PersistentApplicationEventMulticaster.java
@@ -15,6 +15,7 @@
  */
 package org.springframework.modulith.events.support;
 
+import java.lang.reflect.Method;
 import java.time.Duration;
 import java.util.Collection;
 import java.util.List;
@@ -31,6 +32,7 @@
 import org.springframework.context.PayloadApplicationEvent;
 import org.springframework.context.event.AbstractApplicationEventMulticaster;
 import org.springframework.context.event.ApplicationEventMulticaster;
+import org.springframework.context.event.ApplicationListenerMethodAdapter;
 import org.springframework.core.ResolvableType;
 import org.springframework.core.annotation.AnnotationAwareOrderComparator;
 import org.springframework.core.env.Environment;
@@ -46,6 +48,7 @@
 import org.springframework.transaction.event.TransactionalApplicationListener;
 import org.springframework.transaction.event.TransactionalEventListener;
 import org.springframework.util.Assert;
+import org.springframework.util.ReflectionUtils;
 
 /**
  * An {@link ApplicationEventMulticaster} to register {@link EventPublication}s in an {@link EventPublicationRegistry}
@@ -62,11 +65,17 @@ public class PersistentApplicationEventMulticaster extends AbstractApplicationEv
 		implements IncompleteEventPublications, SmartInitializingSingleton {
 
 	private static final Logger LOGGER = LoggerFactory.getLogger(PersistentApplicationEventMulticaster.class);
+	private static final Method SUPPORTS_METHOD = ReflectionUtils.findMethod(ApplicationListenerMethodAdapter.class,
+			"shouldHandle", ApplicationEvent.class, Object[].class);
 	static final String REPUBLISH_ON_RESTART = "spring.modulith.republish-outstanding-events-on-restart";
 
 	private final @NonNull Supplier<EventPublicationRegistry> registry;
 	private final @NonNull Supplier<Environment> environment;
 
+	static {
+		ReflectionUtils.makeAccessible(SUPPORTS_METHOD);
+	}
+
 	/**
 	 * Creates a new {@link PersistentApplicationEventMulticaster} for the given {@link EventPublicationRegistry}.
 	 *
@@ -127,14 +136,14 @@ protected Collection<ApplicationListener<?>> getApplicationListeners(Application
 
 		return super.getApplicationListeners(event, eventType)
 				.stream()
-				.filter(it -> matches(eventToPersist, it))
+				.filter(it -> matches(event, eventToPersist, it))
 				.toList();
 	}
 
-		/*
-	 * (non-Javadoc)
-	 * @see org.springframework.modulith.events.IncompleteEventPublications#resubmitIncompletePublications(java.util.function.Predicate)
-	 */
+	/*
+	* (non-Javadoc)
+	* @see org.springframework.modulith.events.IncompleteEventPublications#resubmitIncompletePublications(java.util.function.Predicate)
+	*/
 	@Override
 	public void resubmitIncompletePublications(Predicate<EventPublication> filter) {
 		doResubmitUncompletedPublicationsOlderThan(null);
@@ -219,10 +228,22 @@ private static Object getEventToPersist(ApplicationEvent event) {
 				: event;
 	}
 
-	private static boolean matches(Object event, ApplicationListener<?> listener) {
+	@SuppressWarnings("null")
+	private static boolean matches(ApplicationEvent event, Object payload, ApplicationListener<?> listener) {
+
+		// Verify general listener matching by eagerly evaluating the condition
+		if (ApplicationListenerMethodAdapter.class.isInstance(listener)) {
+
+			boolean result = (boolean) ReflectionUtils.invokeMethod(SUPPORTS_METHOD, listener, event,
+					new Object[] { payload });
+
+			if (!result) {
+				return false;
+			}
+		}
 
 		return ConditionalEventListener.class.isInstance(listener)
-				? ConditionalEventListener.class.cast(listener).supports(event)
+				? ConditionalEventListener.class.cast(listener).supports(payload)
 				: true;
 	}
 
diff --git a/spring-modulith-events/spring-modulith-events-core/src/test/java/org/springframework/modulith/events/support/PersistentApplicationEventMulticasterUnitTests.java b/spring-modulith-events/spring-modulith-events-core/src/test/java/org/springframework/modulith/events/support/PersistentApplicationEventMulticasterUnitTests.java
index 9448c0082..7f1a88f06 100644
--- a/spring-modulith-events/spring-modulith-events-core/src/test/java/org/springframework/modulith/events/support/PersistentApplicationEventMulticasterUnitTests.java
+++ b/spring-modulith-events/spring-modulith-events-core/src/test/java/org/springframework/modulith/events/support/PersistentApplicationEventMulticasterUnitTests.java
@@ -15,15 +15,25 @@
  */
 package org.springframework.modulith.events.support;
 
+import static org.assertj.core.api.Assertions.*;
 import static org.mockito.Mockito.*;
 
+import lombok.AllArgsConstructor;
+
 import java.util.Map;
 
 import org.junit.jupiter.api.BeforeEach;
 import org.junit.jupiter.api.Test;
+import org.springframework.context.PayloadApplicationEvent;
+import org.springframework.context.annotation.AnnotationConfigApplicationContext;
+import org.springframework.context.event.ApplicationEventMulticaster;
+import org.springframework.context.event.EventListenerMethodProcessor;
+import org.springframework.core.ResolvableType;
 import org.springframework.core.env.MapPropertySource;
 import org.springframework.core.env.StandardEnvironment;
 import org.springframework.modulith.events.core.EventPublicationRegistry;
+import org.springframework.stereotype.Component;
+import org.springframework.transaction.event.TransactionalEventListener;
 
 /**
  * Unit tests for {@link PersistentApplicationEventMulticaster}.
@@ -61,4 +71,39 @@ void triggersRepublicationIfExplicitlyEnabled() {
 
 		verify(registry).findIncompletePublications();
 	}
+
+	@Test // GH-277
+	void honorsListenerCondition() throws Exception {
+
+		try (var ctx = new AnnotationConfigApplicationContext()) {
+
+			ctx.addBeanFactoryPostProcessor(new EventListenerMethodProcessor());
+			ctx.registerBean("applicationEventMulticaster", ApplicationEventMulticaster.class, () -> multicaster);
+			ctx.registerBean("conditionalListener", ConditionalListener.class);
+			ctx.refresh();
+
+			assertListenerSelected(new SampleEvent(true), true);
+			assertListenerSelected(new SampleEvent(false), false);
+		}
+	}
+
+	private void assertListenerSelected(SampleEvent event, boolean expected) {
+
+		var listeners = multicaster.getApplicationListeners(new PayloadApplicationEvent<>(this, event),
+				ResolvableType.forClass(event.getClass()));
+
+		assertThat(listeners).hasSize(expected ? 1 : 0);
+	}
+
+	@Component
+	static class ConditionalListener {
+
+		@TransactionalEventListener(condition = "#event.supported")
+		void on(SampleEvent event) {}
+	}
+
+	@AllArgsConstructor
+	static class SampleEvent {
+		public boolean supported;
+	}
 }