diff --git a/dd-java-agent/dd-java-agent.gradle b/dd-java-agent/dd-java-agent.gradle
index a9e5da0f71..d47ee5eac6 100644
--- a/dd-java-agent/dd-java-agent.gradle
+++ b/dd-java-agent/dd-java-agent.gradle
@@ -23,6 +23,8 @@ def includeShadowJar(subproject, jarname) {
       from(zipTree(subproject.tasks.shadowJar.archivePath)) {
         into jarname
         rename '(^.*)\\.class$', '$1.classdata'
+        // Rename LICENSE file since it clashes with license dir on non-case sensitive FSs (i.e. Mac)
+        rename '^LICENSE$', 'LICENSE.renamed'
       }
     }