diff --git a/gradle/wrapper/gradle-wrapper.properties b/gradle/wrapper/gradle-wrapper.properties
index 74bb77845..933b6473c 100644
--- a/gradle/wrapper/gradle-wrapper.properties
+++ b/gradle/wrapper/gradle-wrapper.properties
@@ -2,4 +2,4 @@ distributionBase=GRADLE_USER_HOME
 distributionPath=wrapper/dists
 zipStoreBase=GRADLE_USER_HOME
 zipStorePath=wrapper/dists
-distributionUrl=https\://services.gradle.org/distributions/gradle-4.2.1-bin.zip
+distributionUrl=https\://services.gradle.org/distributions/gradle-4.4-bin.zip
diff --git a/src/main/groovy/com/github/jengelman/gradle/plugins/shadow/ShadowApplicationPlugin.groovy b/src/main/groovy/com/github/jengelman/gradle/plugins/shadow/ShadowApplicationPlugin.groovy
index 6c1b2d79f..39e5d8e27 100644
--- a/src/main/groovy/com/github/jengelman/gradle/plugins/shadow/ShadowApplicationPlugin.groovy
+++ b/src/main/groovy/com/github/jengelman/gradle/plugins/shadow/ShadowApplicationPlugin.groovy
@@ -89,7 +89,7 @@ class ShadowApplicationPlugin implements Plugin<Project> {
         Sync installTask = project.tasks.getByName(SHADOW_INSTALL_TASK_NAME)
         installTask.doFirst { Sync task ->
             if (task.destinationDir.directory) {
-                if (!new File(task.destinationDir, 'lib').directory || !new File(task.destinationDir, 'bin').directory) {
+                if (task.destinationDir.listFiles().size() != 0 && (!new File(task.destinationDir, 'lib').directory || !new File(task.destinationDir, 'bin').directory)) {
                     throw new GradleException("The specified installation directory '${task.destinationDir}' is neither empty nor does it contain an installation for '${pluginConvention.applicationName}'.\n" +
                             "If you really want to install to this directory, delete it and run the install task again.\n" +
                             "Alternatively, choose a different installation directory."
diff --git a/src/test/groovy/com/github/jengelman/gradle/plugins/shadow/ShadowPluginSpec.groovy b/src/test/groovy/com/github/jengelman/gradle/plugins/shadow/ShadowPluginSpec.groovy
index 6421f3084..7eafa08f3 100644
--- a/src/test/groovy/com/github/jengelman/gradle/plugins/shadow/ShadowPluginSpec.groovy
+++ b/src/test/groovy/com/github/jengelman/gradle/plugins/shadow/ShadowPluginSpec.groovy
@@ -86,7 +86,7 @@ class ShadowPluginSpec extends PluginSpecification {
         assert output.exists()
 
         where:
-        version << ['3.0', '3.1', '3.2', '3.3', '3.4', '3.5', '4.0', '4.1', '4.2', '4.3']
+        version << ['3.0', '3.1', '3.2', '3.3', '3.4', '3.5', '4.0', '4.1', '4.2', '4.3', '4.4']
     }
 
     def 'Error in Gradle versions < 3.0'() {