diff --git a/core/src/main/java/org/testcontainers/containers/wait/strategy/WaitAllStrategy.java b/core/src/main/java/org/testcontainers/containers/wait/strategy/WaitAllStrategy.java
index 5c7530fc67f..ca32e5ba4a2 100644
--- a/core/src/main/java/org/testcontainers/containers/wait/strategy/WaitAllStrategy.java
+++ b/core/src/main/java/org/testcontainers/containers/wait/strategy/WaitAllStrategy.java
@@ -88,7 +88,9 @@ public WaitAllStrategy withStartupTimeout(Duration startupTimeout) {
         }
 
         this.timeout = startupTimeout;
-        strategies.forEach(this::applyStartupTimeout);
+        if (mode == Mode.WITH_OUTER_TIMEOUT) {
+            strategies.forEach(this::applyStartupTimeout);
+        }
         return this;
     }
 
diff --git a/core/src/test/java/org/testcontainers/containers/wait/strategy/WaitAllStrategyTest.java b/core/src/test/java/org/testcontainers/containers/wait/strategy/WaitAllStrategyTest.java
index aeebe425776..7fdaa18e625 100644
--- a/core/src/test/java/org/testcontainers/containers/wait/strategy/WaitAllStrategyTest.java
+++ b/core/src/test/java/org/testcontainers/containers/wait/strategy/WaitAllStrategyTest.java
@@ -11,6 +11,7 @@
 import java.time.Duration;
 
 import static org.assertj.core.api.Assertions.assertThat;
+import static org.assertj.core.api.Assertions.assertThatCode;
 import static org.assertj.core.api.Assertions.catchThrowable;
 import static org.mockito.ArgumentMatchers.any;
 import static org.mockito.ArgumentMatchers.eq;
@@ -90,6 +91,61 @@ void parentTimeoutAppliesToAdditionalChildren() {
             .isEqualTo(20L);
     }
 
+    @Test
+    void maximumOuterTimeoutPreservesChildrenAddedAfterTimeout() {
+        DummyStrategy child1 = new DummyStrategy(Duration.ofSeconds(5));
+        DummyStrategy child2 = new DummyStrategy(Duration.ofSeconds(10));
+
+        new WaitAllStrategy(WaitAllStrategy.Mode.WITH_MAXIMUM_OUTER_TIMEOUT)
+            .withStartupTimeout(Duration.ofSeconds(60))
+            .withStrategy(child1)
+            .withStrategy(child2);
+
+        assertThat(child1.startupTimeout).isEqualTo(Duration.ofSeconds(5));
+        assertThat(child2.startupTimeout).isEqualTo(Duration.ofSeconds(10));
+    }
+
+    @Test
+    void maximumOuterTimeoutPreservesChildrenAddedBeforeTimeout() {
+        DummyStrategy child1 = new DummyStrategy(Duration.ofSeconds(5));
+        DummyStrategy child2 = new DummyStrategy(Duration.ofSeconds(10));
+
+        new WaitAllStrategy(WaitAllStrategy.Mode.WITH_MAXIMUM_OUTER_TIMEOUT)
+            .withStrategy(child1)
+            .withStrategy(child2)
+            .withStartupTimeout(Duration.ofSeconds(60));
+
+        assertThat(child1.startupTimeout).isEqualTo(Duration.ofSeconds(5));
+        assertThat(child2.startupTimeout).isEqualTo(Duration.ofSeconds(10));
+    }
+
+    @Test
+    void maximumOuterTimeoutPreservesChildrenWhenTimeoutChanges() {
+        DummyStrategy child1 = new DummyStrategy(Duration.ofSeconds(5));
+        DummyStrategy child2 = new DummyStrategy(Duration.ofSeconds(10));
+
+        new WaitAllStrategy(WaitAllStrategy.Mode.WITH_MAXIMUM_OUTER_TIMEOUT)
+            .withStrategy(child1)
+            .withStartupTimeout(Duration.ofSeconds(60))
+            .withStrategy(child2)
+            .withStartupTimeout(Duration.ofSeconds(90));
+
+        assertThat(child1.startupTimeout).isEqualTo(Duration.ofSeconds(5));
+        assertThat(child2.startupTimeout).isEqualTo(Duration.ofSeconds(10));
+    }
+
+    @Test
+    void maximumOuterTimeoutAllowsNestedIndividualTimeoutStrategy() {
+        WaitAllStrategy child = new WaitAllStrategy(WaitAllStrategy.Mode.WITH_INDIVIDUAL_TIMEOUTS_ONLY);
+
+        assertThatCode(() -> {
+                new WaitAllStrategy(WaitAllStrategy.Mode.WITH_MAXIMUM_OUTER_TIMEOUT)
+                    .withStrategy(child)
+                    .withStartupTimeout(Duration.ofSeconds(60));
+            })
+            .doesNotThrowAnyException();
+    }
+
     /*
      * Mock-based tests to check overall behaviour, without involving timing-sensitive code
      */