diff --git a/buildSrc/src/main/groovy/MuzzlePlugin.groovy b/buildSrc/src/main/groovy/MuzzlePlugin.groovy
index 3c8507f1ac..dfd7ea8e4e 100644
--- a/buildSrc/src/main/groovy/MuzzlePlugin.groovy
+++ b/buildSrc/src/main/groovy/MuzzlePlugin.groovy
@@ -103,6 +103,13 @@ class MuzzlePlugin implements Plugin<Project> {
         muzzleDirectiveToArtifacts(muzzleDirective, system, session).collect() { Artifact singleVersion ->
           runAfter = addMuzzleTask(muzzleDirective, singleVersion, project, runAfter, bootstrapProject, toolingProject)
         }
+        if (muzzleDirective.assertInverse) {
+          inverseOf(muzzleDirective, system, session).collect() { MuzzleDirective inverseDirective ->
+            muzzleDirectiveToArtifacts(inverseDirective, system, session).collect() { Artifact singleVersion ->
+              runAfter = addMuzzleTask(inverseDirective, singleVersion, project, runAfter, bootstrapProject, toolingProject)
+            }
+          }
+        }
       }
     }
   }
@@ -179,6 +186,41 @@ class MuzzlePlugin implements Plugin<Project> {
     return allVersionArtifacts
   }
 
+  /**
+   * Create a list of muzzle directives which assert the opposite of the given MuzzleDirective.
+   */
+  private static List<MuzzleDirective> inverseOf(MuzzleDirective muzzleDirective, RepositorySystem system, RepositorySystemSession session) {
+    List<MuzzleDirective> inverseDirectives = new ArrayList<>()
+
+    final Artifact allVerisonsArtifact = new DefaultArtifact(muzzleDirective.group, muzzleDirective.module, "jar", "[,)")
+    final Artifact directiveArtifact = new DefaultArtifact(muzzleDirective.group, muzzleDirective.module, "jar", muzzleDirective.versions)
+
+
+    final VersionRangeRequest allRangeRequest = new VersionRangeRequest()
+    allRangeRequest.setRepositories(MUZZLE_REPOS)
+    allRangeRequest.setArtifact(allVerisonsArtifact)
+    final VersionRangeResult allRangeResult = system.resolveVersionRange(session, allRangeRequest)
+
+    final VersionRangeRequest rangeRequest = new VersionRangeRequest()
+    rangeRequest.setRepositories(MUZZLE_REPOS)
+    rangeRequest.setArtifact(directiveArtifact)
+    final VersionRangeResult rangeResult = system.resolveVersionRange(session, rangeRequest)
+
+    filterVersion(allRangeResult.versions).collect { version ->
+      if (!rangeResult.versions.contains(version)) {
+        final MuzzleDirective inverseDirective = new MuzzleDirective()
+        inverseDirective.group = muzzleDirective.group
+        inverseDirective.module = muzzleDirective.module
+        inverseDirective.versions = "$version"
+        inverseDirective.assertPass = !muzzleDirective.assertPass
+        inverseDirectives.add(inverseDirective)
+      }
+    }
+
+    return inverseDirectives
+  }
+
+
   /**
    * Configure a muzzle task to pass or fail a given version.
    *
@@ -272,6 +314,7 @@ class MuzzleDirective {
   String versions
   List<String> additionalDependencies = new ArrayList<>()
   boolean assertPass
+  boolean assertInverse = false
   void extraDependency(String compileString) {
     additionalDependencies.add(compileString)
   }
diff --git a/dd-java-agent/instrumentation/apache-httpclient-4.3/apache-httpclient-4.3.gradle b/dd-java-agent/instrumentation/apache-httpclient-4.3/apache-httpclient-4.3.gradle
index bed8c30d1f..75abaff407 100644
--- a/dd-java-agent/instrumentation/apache-httpclient-4.3/apache-httpclient-4.3.gradle
+++ b/dd-java-agent/instrumentation/apache-httpclient-4.3/apache-httpclient-4.3.gradle
@@ -1,21 +1,17 @@
 apply from: "${rootDir}/gradle/java.gradle"
 
 muzzle {
-  pass {
-    group = "org.apache.httpcomponents"
-    module = "httpclient"
-    versions = "[4.3,)"
-  }
-  fail {
-    group = "org.apache.httpcomponents"
-    module = "httpclient"
-    versions = "[,4.3)"
-  }
   fail {
     group = "commons-httpclient"
     module = "commons-httpclient"
     versions = "[,4.3)"
   }
+  pass {
+    group = "org.apache.httpcomponents"
+    module = "httpclient"
+    versions = "[4.3,)"
+    assertInverse = true
+  }
 }
 
 apply plugin: 'org.unbroken-dome.test-sets'