diff --git a/src/main/resources/META-INF/rewrite/assertj.yml b/src/main/resources/META-INF/rewrite/assertj.yml
index 28b7eae0b..1ae70b513 100644
--- a/src/main/resources/META-INF/rewrite/assertj.yml
+++ b/src/main/resources/META-INF/rewrite/assertj.yml
@@ -110,16 +110,31 @@ recipeList:
       assertToReplace: isTrue
       dedicatedAssertion: startsWith
       requiredType: java.lang.String
+  - org.openrewrite.java.testing.assertj.SimplifyChainedAssertJAssertion:
+      chainedAssertion: startsWith
+      assertToReplace: isFalse
+      dedicatedAssertion: doesNotStartWith
+      requiredType: java.lang.String
   - org.openrewrite.java.testing.assertj.SimplifyChainedAssertJAssertion:
       chainedAssertion: endsWith
       assertToReplace: isTrue
       dedicatedAssertion: endsWith
       requiredType: java.lang.String
+  - org.openrewrite.java.testing.assertj.SimplifyChainedAssertJAssertion:
+      chainedAssertion: endsWith
+      assertToReplace: isFalse
+      dedicatedAssertion: doesNotEndWith
+      requiredType: java.lang.String
   - org.openrewrite.java.testing.assertj.SimplifyChainedAssertJAssertion:
       chainedAssertion: matches
       assertToReplace: isTrue
       dedicatedAssertion: matches
       requiredType: java.lang.String
+  - org.openrewrite.java.testing.assertj.SimplifyChainedAssertJAssertion:
+      chainedAssertion: matches
+      assertToReplace: isFalse
+      dedicatedAssertion: doesNotMatch
+      requiredType: java.lang.String
   - org.openrewrite.java.testing.assertj.SimplifyChainedAssertJAssertion:
       chainedAssertion: trim
       assertToReplace: isEmpty
diff --git a/src/test/java/org/openrewrite/java/testing/assertj/SimplifyChainedAssertJAssertionsTest.java b/src/test/java/org/openrewrite/java/testing/assertj/SimplifyChainedAssertJAssertionsTest.java
index 874d6480b..cc5bed354 100644
--- a/src/test/java/org/openrewrite/java/testing/assertj/SimplifyChainedAssertJAssertionsTest.java
+++ b/src/test/java/org/openrewrite/java/testing/assertj/SimplifyChainedAssertJAssertionsTest.java
@@ -85,8 +85,11 @@ private static Stream<Arguments> stringReplacements() {
               Arguments.arguments("equalsIgnoreCase", "isTrue", "isEqualToIgnoringCase", "expected", ""),
               Arguments.arguments("contains", "isTrue", "contains", "expected", ""),
               Arguments.arguments("startsWith", "isTrue", "startsWith", "expected", ""),
+              Arguments.arguments("startsWith", "isFalse", "doesNotStartWith", "expected", ""),
               Arguments.arguments("endsWith", "isTrue", "endsWith", "expected", ""),
+              Arguments.arguments("endsWith", "isFalse", "doesNotEndWith", "expected", ""),
               Arguments.arguments("matches", "isTrue", "matches", "expected", ""),
+              Arguments.arguments("matches", "isFalse", "doesNotMatch", "expected", ""),
               Arguments.arguments("trim", "isEmpty", "isBlank", "", ""),
               Arguments.arguments("length", "isEqualTo", "hasSize", "", "length"),
               Arguments.arguments("isEmpty", "isFalse", "isNotEmpty", "", "")