diff --git a/buildSrc/build.gradle b/buildSrc/build.gradle
index 0839b8a22f8..73115aab88f 100644
--- a/buildSrc/build.gradle
+++ b/buildSrc/build.gradle
@@ -94,6 +94,7 @@ dependencies {
   compile 'com.perforce:p4java:2012.3.551082' // THIS IS SUPPOSED TO BE OPTIONAL IN THE FUTURE....
   compile 'de.thetaphi:forbiddenapis:2.3'
   compile 'org.apache.rat:apache-rat:0.11'
+  compile "org.elasticsearch:jna:4.4.0-1"
 }
 
 // Gradle 2.14+ removed ProgressLogger(-Factory) classes from the public APIs
diff --git a/buildSrc/src/main/groovy/org/elasticsearch/gradle/test/ClusterFormationTasks.groovy b/buildSrc/src/main/groovy/org/elasticsearch/gradle/test/ClusterFormationTasks.groovy
index d6eeb2f4447..d1a67597dd9 100644
--- a/buildSrc/src/main/groovy/org/elasticsearch/gradle/test/ClusterFormationTasks.groovy
+++ b/buildSrc/src/main/groovy/org/elasticsearch/gradle/test/ClusterFormationTasks.groovy
@@ -206,7 +206,19 @@ class ClusterFormationTasks {
         for (Map.Entry<String, Object[]> command : node.config.setupCommands.entrySet()) {
             // the first argument is the actual script name, relative to home
             Object[] args = command.getValue().clone()
-            args[0] = new File(node.homeDir, args[0].toString())
+            final Object commandPath
+            if (Os.isFamily(Os.FAMILY_WINDOWS)) {
+                /*
+                 * We have to delay building the string as the path will not exist during configuration which will fail on Windows due to
+                 * getting the short name requiring the path to already exist. Note that we have to capture the value of arg[0] now
+                 * otherwise we would stack overflow later since arg[0] is replaced below.
+                 */
+                String argsZero = args[0]
+                commandPath = "${-> Paths.get(NodeInfo.getShortPathName(node.homeDir.toString())).resolve(argsZero.toString()).toString()}"
+            } else {
+                commandPath = node.homeDir.toPath().resolve(args[0].toString()).toString()
+            }
+            args[0] = commandPath
             setup = configureExecTask(taskName(prefix, node, command.getKey()), project, setup, node, args)
         }
 
@@ -337,7 +349,11 @@ class ClusterFormationTasks {
         if (node.config.keystoreSettings.isEmpty()) {
             return setup
         } else {
-            File esKeystoreUtil = Paths.get(node.homeDir.toString(), "bin/" + "elasticsearch-keystore").toFile()
+            /*
+             * We have to delay building the string as the path will not exist during configuration which will fail on Windows due to
+             * getting the short name requiring the path to already exist.
+             */
+            final Object esKeystoreUtil = "${-> node.binPath().resolve('elasticsearch-keystore').toString()}"
             return configureExecTask(name, project, setup, node, esKeystoreUtil, 'create')
         }
     }
@@ -345,8 +361,12 @@ class ClusterFormationTasks {
     /** Adds tasks to add settings to the keystore */
     static Task configureAddKeystoreSettingTasks(String parent, Project project, Task setup, NodeInfo node) {
         Map kvs = node.config.keystoreSettings
-        File esKeystoreUtil = Paths.get(node.homeDir.toString(), "bin/" + "elasticsearch-keystore").toFile()
         Task parentTask = setup
+        /*
+         * We have to delay building the string as the path will not exist during configuration which will fail on Windows due to getting
+         * the short name requiring the path to already exist.
+         */
+        final Object esKeystoreUtil = "${-> node.binPath().resolve('elasticsearch-keystore').toString()}"
         for (Map.Entry<String, String> entry in kvs) {
             String key = entry.getKey()
             String name = taskName(parent, node, 'addToKeystore#' + key)
@@ -482,8 +502,13 @@ class ClusterFormationTasks {
             pluginZip = project.configurations.getByName("_plugin_${prefix}_${plugin.path}")
         }
         // delay reading the file location until execution time by wrapping in a closure within a GString
-        Object file = "${-> new File(node.pluginsTmpDir, pluginZip.singleFile.getName()).toURI().toURL().toString()}"
-        Object[] args = [new File(node.homeDir, 'bin/elasticsearch-plugin'), 'install', file]
+        final Object file = "${-> new File(node.pluginsTmpDir, pluginZip.singleFile.getName()).toURI().toURL().toString()}"
+        /*
+         * We have to delay building the string as the path will not exist during configuration which will fail on Windows due to getting
+         * the short name requiring the path to already exist.
+         */
+        final Object esPluginUtil = "${-> node.binPath().resolve('elasticsearch-plugin').toString()}"
+        final Object[] args = [esPluginUtil, 'install', file]
         return configureExecTask(name, project, setup, node, args)
     }
 
diff --git a/buildSrc/src/main/groovy/org/elasticsearch/gradle/test/JNAKernel32Library.java b/buildSrc/src/main/groovy/org/elasticsearch/gradle/test/JNAKernel32Library.java
new file mode 100644
index 00000000000..4d069cd434f
--- /dev/null
+++ b/buildSrc/src/main/groovy/org/elasticsearch/gradle/test/JNAKernel32Library.java
@@ -0,0 +1,25 @@
+package org.elasticsearch.gradle.test;
+
+import com.sun.jna.Native;
+import com.sun.jna.WString;
+import org.apache.tools.ant.taskdefs.condition.Os;
+
+public class JNAKernel32Library {
+
+    private static final class Holder {
+        private static final JNAKernel32Library instance = new JNAKernel32Library();
+    }
+
+    static JNAKernel32Library getInstance() {
+        return Holder.instance;
+    }
+
+    private JNAKernel32Library() {
+        if (Os.isFamily(Os.FAMILY_WINDOWS)) {
+            Native.register("kernel32");
+        }
+    }
+
+    native int GetShortPathNameW(WString lpszLongPath, char[] lpszShortPath, int cchBuffer);
+
+}
diff --git a/buildSrc/src/main/groovy/org/elasticsearch/gradle/test/NodeInfo.groovy b/buildSrc/src/main/groovy/org/elasticsearch/gradle/test/NodeInfo.groovy
index 9aadc5cf4a4..de48a20dc49 100644
--- a/buildSrc/src/main/groovy/org/elasticsearch/gradle/test/NodeInfo.groovy
+++ b/buildSrc/src/main/groovy/org/elasticsearch/gradle/test/NodeInfo.groovy
@@ -18,11 +18,16 @@
  */
 package org.elasticsearch.gradle.test
 
+import com.sun.jna.Native
+import com.sun.jna.WString
 import org.apache.tools.ant.taskdefs.condition.Os
 import org.elasticsearch.gradle.Version
 import org.gradle.api.InvalidUserDataException
 import org.gradle.api.Project
 
+import java.nio.file.Path
+import java.nio.file.Paths
+
 /**
  * A container for the files and configuration associated with a single node in a test cluster.
  */
@@ -85,10 +90,10 @@ class NodeInfo {
     String executable
 
     /** Path to the elasticsearch start script */
-    File esScript
+    private Object esScript
 
     /** script to run when running in the background */
-    File wrapperScript
+    private File wrapperScript
 
     /** buffer for ant output when starting this node */
     ByteArrayOutputStream buffer = new ByteArrayOutputStream()
@@ -132,11 +137,15 @@ class NodeInfo {
             args.add('/C')
             args.add('"') // quote the entire command
             wrapperScript = new File(cwd, "run.bat")
-            esScript = new File(homeDir, 'bin/elasticsearch.bat')
+            /*
+             * We have to delay building the string as the path will not exist during configuration which will fail on Windows due to
+             * getting the short name requiring the path to already exist.
+             */
+            esScript = "${-> binPath().resolve('elasticsearch.bat').toString()}"
         } else {
             executable = 'bash'
             wrapperScript = new File(cwd, "run")
-            esScript = new File(homeDir, 'bin/elasticsearch')
+            esScript = binPath().resolve('elasticsearch')
         }
         if (config.daemonize) {
             args.add("${wrapperScript}")
@@ -170,6 +179,31 @@ class NodeInfo {
         }
     }
 
+    Path binPath() {
+        if (Os.isFamily(Os.FAMILY_WINDOWS)) {
+            return Paths.get(getShortPathName(new File(homeDir, 'bin').toString()))
+        } else {
+            return Paths.get(new File(homeDir, 'bin').toURI())
+        }
+    }
+
+    static String getShortPathName(String path) {
+        assert Os.isFamily(Os.FAMILY_WINDOWS)
+        final WString longPath = new WString("\\\\?\\" + path)
+        // first we get the length of the buffer needed
+        final int length = JNAKernel32Library.getInstance().GetShortPathNameW(longPath, null, 0)
+        if (length == 0) {
+            throw new IllegalStateException("path [" + path + "] encountered error [" + Native.getLastError() + "]")
+        }
+        final char[] shortPath = new char[length]
+        // knowing the length of the buffer, now we get the short name
+        if (JNAKernel32Library.getInstance().GetShortPathNameW(longPath, shortPath, length) == 0) {
+            throw new IllegalStateException("path [" + path + "] encountered error [" + Native.getLastError() + "]")
+        }
+        // we have to strip the \\?\ away from the path for cmd.exe
+        return Native.toString(shortPath).substring(4)
+    }
+
     /** Returns debug string for the command that started this node. */
     String getCommandString() {
         String esCommandString = "\nNode ${nodeNum} configuration:\n"
diff --git a/buildSrc/version.properties b/buildSrc/version.properties
index eb39b486e64..1ff107d52e1 100644
--- a/buildSrc/version.properties
+++ b/buildSrc/version.properties
@@ -10,6 +10,8 @@ snakeyaml         = 1.15
 # When updating log4j, please update also docs/java-api/index.asciidoc
 log4j             = 2.8.2
 slf4j             = 1.6.2
+
+# when updating the JNA version, also update the version in buildSrc/build.gradle
 jna               = 4.4.0-1
 
 # test dependencies