diff --git a/src/main/java/org/openrewrite/java/testing/junit5/UpdateTestAnnotation.java b/src/main/java/org/openrewrite/java/testing/junit5/UpdateTestAnnotation.java
index e13765906..39a5b4527 100644
--- a/src/main/java/org/openrewrite/java/testing/junit5/UpdateTestAnnotation.java
+++ b/src/main/java/org/openrewrite/java/testing/junit5/UpdateTestAnnotation.java
@@ -30,7 +30,6 @@
 import org.openrewrite.marker.Markup;
 import org.openrewrite.staticanalysis.LambdaBlockToExpression;
 
-import java.util.Comparator;
 import java.util.List;
 import java.util.Objects;
 import java.util.Set;
@@ -156,18 +155,32 @@ public J.MethodDeclaration visitMethodDeclaration(J.MethodDeclaration method, Ex
                         maybeAddImport("org.junit.jupiter.api.Assertions", "assertThrows", false);
                     }
                 }
-                if (cta.timeout != null) {
-                    m = JavaTemplate.builder("@Timeout(value = #{any(long)}, unit = TimeUnit.MILLISECONDS)")
+                if (cta.timeout != null &&
+                        !J.Literal.isLiteralValue(cta.timeout, 0L) &&
+                        !J.Literal.isLiteralValue(cta.timeout, 0)) {
+                    m = JavaTemplate.builder("org.junit.jupiter.api.function.Executable o = () -> #{};")
                             .javaParser(javaParser)
-                            .imports("org.junit.jupiter.api.Timeout", "java.util.concurrent.TimeUnit")
                             .build()
                             .apply(
                                     updateCursor(m),
-                                    m.getCoordinates().addAnnotation(Comparator.comparing(J.Annotation::getSimpleName)),
-                                    cta.timeout
+                                    m.getCoordinates().replaceBody(),
+                                    m.getBody()
                             );
-                    maybeAddImport("org.junit.jupiter.api.Timeout");
-                    maybeAddImport("java.util.concurrent.TimeUnit");
+
+                    assert m.getBody() != null;
+                    J.Lambda lambda = (J.Lambda) ((J.VariableDeclarations) m.getBody().getStatements().get(0))
+                            .getVariables().get(0).getInitializer();
+
+                    assert lambda != null;
+
+                    m = JavaTemplate.builder("assertTimeoutPreemptively(Duration.ofMillis(#{any(long)}), #{any(org.junit.jupiter.api.function.Executable)});")
+                            .javaParser(javaParser)
+                            .staticImports("org.junit.jupiter.api.Assertions.assertTimeoutPreemptively")
+                            .imports("java.time.Duration")
+                            .build()
+                            .apply(updateCursor(m), m.getCoordinates().replaceBody(), cta.timeout, lambda);
+                    maybeAddImport("org.junit.jupiter.api.Assertions", "assertTimeoutPreemptively", false);
+                    maybeAddImport("java.time.Duration");
                 }
                 maybeAddImport("org.junit.jupiter.api.Test");
 
diff --git a/src/test/java/org/openrewrite/java/testing/junit5/UpdateTestAnnotationTest.java b/src/test/java/org/openrewrite/java/testing/junit5/UpdateTestAnnotationTest.java
index 9f29a01cd..9a8ff2f0e 100644
--- a/src/test/java/org/openrewrite/java/testing/junit5/UpdateTestAnnotationTest.java
+++ b/src/test/java/org/openrewrite/java/testing/junit5/UpdateTestAnnotationTest.java
@@ -335,6 +335,7 @@ public void test2() {
     }
 
     @Issue("https://github.com/openrewrite/rewrite-testing-frameworks/issues/450")
+    @Issue("https://github.com/openrewrite/rewrite-testing-frameworks/issues/1073")
     @Test
     void annotationWithTimeout() {
         //language=java
@@ -352,15 +353,89 @@ public void test() {
               """,
             """
               import org.junit.jupiter.api.Test;
-              import org.junit.jupiter.api.Timeout;
 
-              import java.util.concurrent.TimeUnit;
+              import java.time.Duration;
+
+              import static org.junit.jupiter.api.Assertions.assertTimeoutPreemptively;
 
               public class MyTest {
 
                   @Test
-                  @Timeout(value = 500, unit = TimeUnit.MILLISECONDS)
                   public void test() {
+                      assertTimeoutPreemptively(Duration.ofMillis(500), () -> {
+                      });
+                  }
+              }
+              """
+          )
+        );
+    }
+
+    @Issue("https://github.com/openrewrite/rewrite-testing-frameworks/issues/1073")
+    @Test
+    void timeoutZeroIsNoOpInJUnit4SoAnnotationOnlyMigrated() {
+        //language=java
+        rewriteRun(
+          java(
+            """
+              import org.junit.Test;
+
+              public class MyTest {
+
+                  @Test(timeout = 0)
+                  public void test() {
+                      String foo = "foo";
+                  }
+              }
+              """,
+            """
+              import org.junit.jupiter.api.Test;
+
+              public class MyTest {
+
+                  @Test
+                  public void test() {
+                      String foo = "foo";
+                  }
+              }
+              """
+          )
+        );
+    }
+
+    @Issue("https://github.com/openrewrite/rewrite-testing-frameworks/issues/1073")
+    @Test
+    void annotationWithTimeoutAndStatements() {
+        //language=java
+        rewriteRun(
+          java(
+            """
+              import org.junit.Test;
+
+              public class MyTest {
+
+                  @Test(timeout = 500)
+                  public void test() {
+                      String foo = "foo";
+                      System.out.println(foo);
+                  }
+              }
+              """,
+            """
+              import org.junit.jupiter.api.Test;
+
+              import java.time.Duration;
+
+              import static org.junit.jupiter.api.Assertions.assertTimeoutPreemptively;
+
+              public class MyTest {
+
+                  @Test
+                  public void test() {
+                      assertTimeoutPreemptively(Duration.ofMillis(500), () -> {
+                          String foo = "foo";
+                          System.out.println(foo);
+                      });
                   }
               }
               """
@@ -415,6 +490,7 @@ public void test() {
         );
     }
 
+    @Issue("https://github.com/openrewrite/rewrite-testing-frameworks/issues/1073")
     @Test
     void annotationWithTimeoutAndException() {
         //language=java
@@ -433,19 +509,20 @@ public void test() {
               """,
             """
               import org.junit.jupiter.api.Test;
-              import org.junit.jupiter.api.Timeout;
 
-              import java.util.concurrent.TimeUnit;
+              import java.time.Duration;
 
               import static org.junit.jupiter.api.Assertions.assertThrows;
+              import static org.junit.jupiter.api.Assertions.assertTimeoutPreemptively;
 
               public class MyTest {
 
                   @Test
-                  @Timeout(value = 500, unit = TimeUnit.MILLISECONDS)
                   public void test() {
-                      assertThrows(IllegalArgumentException.class, () -> {
-                          throw new IllegalArgumentException("boom");
+                      assertTimeoutPreemptively(Duration.ofMillis(500), () -> {
+                          assertThrows(IllegalArgumentException.class, () -> {
+                              throw new IllegalArgumentException("boom");
+                          });
                       });
                   }
               }
@@ -496,7 +573,6 @@ public void foo() {
         );
     }
 
-
     @Test
     void migrateDotClass() {
         //language=java
@@ -550,8 +626,8 @@ public void test() {
 
     @Test
     void fullyQualified() {
+        //language=java
         rewriteRun(
-          //language=java
           java(
             """
               public class MyTest {
@@ -575,8 +651,8 @@ public void feature1() {
 
     @Test
     void mixedFullyQualifiedAndNot() {
+        //language=java
         rewriteRun(
-          //language=java
           java(
             """
               import org.junit.Test;