diff --git a/buildSrc/src/main/groovy/org/elasticsearch/gradle/vagrant/VagrantTestPlugin.groovy b/buildSrc/src/main/groovy/org/elasticsearch/gradle/vagrant/VagrantTestPlugin.groovy
index 0fe45c4321ef8..3868e0417f4d8 100644
--- a/buildSrc/src/main/groovy/org/elasticsearch/gradle/vagrant/VagrantTestPlugin.groovy
+++ b/buildSrc/src/main/groovy/org/elasticsearch/gradle/vagrant/VagrantTestPlugin.groovy
@@ -312,7 +312,7 @@ class VagrantTestPlugin implements Plugin<Project> {
                        test_args=( "\$@" )
                      fi
                      
-                     "${-> convertPath(project, linuxGradleJdk.toString()) }"/bin/java -cp "\$PACKAGING_TESTS/*" org.elasticsearch.packaging.VMTestRunner "\${test_args[@]}"
+                     "${-> convertLinuxPath(project, linuxGradleJdk.toString()) }"/bin/java -cp "\$PACKAGING_TESTS/*" org.elasticsearch.packaging.VMTestRunner "\${test_args[@]}"
                      """
         }
         Task createWindowsRunnerScript = project.tasks.create('createWindowsRunnerScript', FileContentsTask) {
@@ -321,13 +321,19 @@ class VagrantTestPlugin implements Plugin<Project> {
             // the use of $args rather than param() here is deliberate because the syntax for array (multivalued) parameters is likely
             // a little trappy for those unfamiliar with powershell
             contents """\
-                     if (\$args.Count -eq 0) {
-                       \$testArgs = @("${-> project.extensions.esvagrant.testClass}")
-                     } else {
-                       \$testArgs = \$args
+                     try {
+                         if (\$args.Count -eq 0) {
+                           \$testArgs = @("${-> project.extensions.esvagrant.testClass}")
+                         } else {
+                           \$testArgs = \$args
+                         }
+                         & "${-> convertWindowsPath(project, windowsGradleJdk.toString()) }/bin/java" -cp "\$Env:PACKAGING_TESTS/*" org.elasticsearch.packaging.VMTestRunner @testArgs
+                         exit \$LASTEXITCODE
+                     } catch {
+                         # catch if we have a failure to even run the script at all above, equivalent to set -e, sort of
+                         echo "\$_.Exception.Message"
+                         exit 1
                      }
-                     & "${-> convertPath(project, windowsGradleJdk.toString()) }"/bin/java -cp "\$Env:PACKAGING_TESTS/*" org.elasticsearch.packaging.VMTestRunner @testArgs
-                     exit \$LASTEXITCODE
                      """
         }
 
@@ -610,7 +616,7 @@ class VagrantTestPlugin implements Plugin<Project> {
                 // https://github.com/hashicorp/vagrant/blob/9c299a2a357fcf87f356bb9d56e18a037a53d138/plugins/communicators/winrm/communicator.rb#L195-L225
                 // https://devops-collective-inc.gitbooks.io/secrets-of-powershell-remoting/content/manuscript/accessing-remote-computers.html
                 javaPackagingTest.command = 'winrm'
-                javaPackagingTest.args = ['--elevated', '--command', 'powershell -File "$Env:PACKAGING_TESTS/run-tests.ps1"']
+                javaPackagingTest.args = ['--elevated', '--command', '& "$Env:PACKAGING_TESTS/run-tests.ps1"; exit $LASTEXITCODE']
             }
 
             TaskExecutionAdapter javaPackagingReproListener = createReproListener(project, javaPackagingTest.path)
@@ -643,7 +649,10 @@ class VagrantTestPlugin implements Plugin<Project> {
     }
 
     // convert the given path from an elasticsearch repo path to a VM path
-    private String convertPath(Project project, String path) {
+    private String convertLinuxPath(Project project, String path) {
         return "/elasticsearch/" + project.rootDir.toPath().relativize(Paths.get(path));
     }
+    private String convertWindowsPath(Project project, String path) {
+        return "C:\\elasticsearch\\" + project.rootDir.toPath().relativize(Paths.get(path)).toString().replace('/', '\\');
+    }
 }
diff --git a/distribution/src/bin/elasticsearch-service.bat b/distribution/src/bin/elasticsearch-service.bat
index 2f9c280743dfb..fd4d4b666dba8 100644
--- a/distribution/src/bin/elasticsearch-service.bat
+++ b/distribution/src/bin/elasticsearch-service.bat
@@ -106,6 +106,10 @@ if exist "%JAVA_HOME%\bin\server\jvm.dll" (
 )
 
 :foundJVM
+if not defined ES_TMPDIR (
+  for /f "tokens=* usebackq" %%a in (`CALL %JAVA% -cp "!ES_CLASSPATH!" "org.elasticsearch.tools.launchers.TempDirectory"`) do set ES_TMPDIR=%%a
+)
+
 set ES_JVM_OPTIONS=%ES_PATH_CONF%\jvm.options
 
 if not "%ES_JAVA_OPTS%" == "" set ES_JAVA_OPTS=%ES_JAVA_OPTS: =;%
diff --git a/qa/vagrant/src/main/java/org/elasticsearch/packaging/test/WindowsServiceTestCase.java b/qa/vagrant/src/main/java/org/elasticsearch/packaging/test/WindowsServiceTestCase.java
index 57eaf13fe9e94..b0827513c9233 100644
--- a/qa/vagrant/src/main/java/org/elasticsearch/packaging/test/WindowsServiceTestCase.java
+++ b/qa/vagrant/src/main/java/org/elasticsearch/packaging/test/WindowsServiceTestCase.java
@@ -92,7 +92,7 @@ private void assertExit(Result result, String script, int exitCode) {
             Result logs = sh.run("$files = Get-ChildItem \"" + installation.logs + "\\elasticsearch.log\"; " +
                 "Write-Output $files; " +
                 "foreach ($file in $files) {" +
-                    "Write-Output \"$file\"; " +    
+                    "Write-Output \"$file\"; " +
                     "Get-Content \"$file\" " +
                 "}");
             logger.error(logs.stdout);