diff --git a/.gitignore b/.gitignore
index d213cf5c9..d622dc1d1 100644
--- a/.gitignore
+++ b/.gitignore
@@ -8,3 +8,4 @@ out/
 bin/
 *.log
 .vscode/
+src/main/generated/
\ No newline at end of file
diff --git a/build.gradle.kts b/build.gradle.kts
index e7ccd9904..c1a91eafc 100644
--- a/build.gradle.kts
+++ b/build.gradle.kts
@@ -37,6 +37,8 @@ dependencies {
     implementation("org.openrewrite.recipe:rewrite-static-analysis:$rewriteVersion")
     runtimeOnly("org.openrewrite:rewrite-java-17")
 
+    compileOnly("org.junit.jupiter:junit-jupiter-engine:latest.release")
+
     compileOnly("org.projectlombok:lombok:latest.release")
     annotationProcessor("org.projectlombok:lombok:latest.release")
 
@@ -47,6 +49,12 @@ dependencies {
     testImplementation("org.openrewrite:rewrite-kotlin:$rewriteVersion")
     testImplementation("org.openrewrite.gradle.tooling:model:$rewriteVersion")
 
+    annotationProcessor("org.openrewrite:rewrite-templating:${rewriteVersion}")
+    implementation("org.openrewrite:rewrite-templating:${rewriteVersion}")
+    compileOnly("com.google.errorprone:error_prone_core:2.19.1:with-dependencies") {
+        exclude("com.google.auto.service", "auto-service-annotations")
+    }
+
     testRuntimeOnly("org.gradle:gradle-tooling-api:latest.release")
 
     testRuntimeOnly("com.tngtech.archunit:archunit:0.23.1")
diff --git a/src/main/java/org/openrewrite/java/testing/cleanup/AssertLiteralBooleanToFail.java b/src/main/java/org/openrewrite/java/testing/cleanup/AssertLiteralBooleanToFail.java
new file mode 100644
index 000000000..e1e53aea7
--- /dev/null
+++ b/src/main/java/org/openrewrite/java/testing/cleanup/AssertLiteralBooleanToFail.java
@@ -0,0 +1,49 @@
+/*
+ * Copyright 2021 the original author or authors.
+ * <p>
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ * <p>
+ * https://www.apache.org/licenses/LICENSE-2.0
+ * <p>
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+package org.openrewrite.java.testing.cleanup;
+
+import com.google.errorprone.refaster.annotation.AfterTemplate;
+import com.google.errorprone.refaster.annotation.BeforeTemplate;
+import com.google.errorprone.refaster.annotation.UseImportPolicy;
+import org.openrewrite.java.template.RecipeDescriptor;
+
+import static com.google.errorprone.refaster.ImportPolicy.STATIC_IMPORT_ALWAYS;
+import static org.junit.jupiter.api.Assertions.*;
+
+@RecipeDescriptor(
+        name = "Replace JUnit `assertTrue(false, \"reason\")` and `assertFalse(true, \"reason\")` with `fail(\"reason\")`",
+        description = "Using fail is more direct and clear."
+)
+public class AssertLiteralBooleanToFail {
+
+    @BeforeTemplate
+    void assertFalseBefore(String message) {
+        assertFalse(true, message);
+    }
+
+    @BeforeTemplate
+    void assertTrueBefore(String message) {
+        assertTrue(false, message);
+    }
+
+    @AfterTemplate
+    // This annotation does not get taken into account
+    // resulting in Assertions.fail(message) being outputted
+    @UseImportPolicy(value = STATIC_IMPORT_ALWAYS)
+    void after(String message) {
+        fail(message);
+    }
+}
diff --git a/src/test/java/org/openrewrite/java/testing/cleanup/AssertLiteralBooleanToFailTest.java b/src/test/java/org/openrewrite/java/testing/cleanup/AssertLiteralBooleanToFailTest.java
new file mode 100644
index 000000000..da773f4b1
--- /dev/null
+++ b/src/test/java/org/openrewrite/java/testing/cleanup/AssertLiteralBooleanToFailTest.java
@@ -0,0 +1,117 @@
+/*
+ * Copyright 2024 the original author or authors.
+ * <p>
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ * <p>
+ * https://www.apache.org/licenses/LICENSE-2.0
+ * <p>
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+package org.openrewrite.java.testing.cleanup;
+
+import org.junit.jupiter.api.Test;
+import org.openrewrite.DocumentExample;
+import org.openrewrite.InMemoryExecutionContext;
+import org.openrewrite.java.JavaParser;
+import org.openrewrite.test.RecipeSpec;
+import org.openrewrite.test.RewriteTest;
+
+import static org.openrewrite.java.Assertions.java;
+
+class AssertLiteralBooleanToFailTest implements RewriteTest {
+
+    @Override
+    public void defaults(RecipeSpec spec) {
+        spec
+          .parser(JavaParser.fromJavaVersion().classpathFromResources(new InMemoryExecutionContext(), "junit-jupiter-api-5.9"))
+          .recipe(new AssertLiteralBooleanToFailRecipe());
+    }
+
+    @Test
+    @DocumentExample
+    @SuppressWarnings("SimplifiableAssertion")
+    void assertWithStaticImports() {
+        //language=java
+        rewriteRun(
+          java(
+            """
+              import static org.junit.jupiter.api.Assertions.assertFalse;
+              import static org.junit.jupiter.api.Assertions.assertTrue;
+
+              public class Test {
+                  void test() {
+                      assertFalse(true, "assert false true");
+                      assertTrue(false, "assert true false");
+                  }
+              }
+              """,
+            """
+              import org.junit.jupiter.api.Assertions;
+
+              public class Test {
+                  void test() {
+                      Assertions.fail("assert false true");
+                      Assertions.fail("assert true false");
+                  }
+              }
+              """
+          )
+        );
+    }
+
+    @Test
+    @SuppressWarnings("SimplifiableAssertion")
+    void assertWithAssertionsImport() {
+        //language=java
+        rewriteRun(
+          java(
+            """
+              import org.junit.jupiter.api.Assertions;
+
+              public class Test {
+                  void test() {
+                      Assertions.assertFalse(true, "assert false true");
+                      Assertions.assertTrue(false, "assert true false");
+                  }
+              }
+              """,
+            """
+              import org.junit.jupiter.api.Assertions;
+
+              public class Test {
+                  void test() {
+                      Assertions.fail("assert false true");
+                      Assertions.fail("assert true false");
+                  }
+              }
+              """
+          )
+        );
+    }
+
+    @Test
+    void noChangeWhenNotLiteral() {
+        //language=java
+        rewriteRun(
+          java(
+            """
+              import static org.junit.jupiter.api.Assertions.assertFalse;
+              import static org.junit.jupiter.api.Assertions.assertTrue;
+
+              public class Test {
+                  void test(boolean a, Object b) {
+                      assertTrue(a, "message");
+                      assertFalse(b.equals("foo"), "message");
+                  }
+              }
+              """
+          )
+        );
+    }
+}