diff --git a/jetty-webapp/src/main/java/org/eclipse/jetty/webapp/WebInfConfiguration.java b/jetty-webapp/src/main/java/org/eclipse/jetty/webapp/WebInfConfiguration.java
index 53ec88c942a1..6fbe03080dd3 100644
--- a/jetty-webapp/src/main/java/org/eclipse/jetty/webapp/WebInfConfiguration.java
+++ b/jetty-webapp/src/main/java/org/eclipse/jetty/webapp/WebInfConfiguration.java
@@ -354,8 +354,10 @@ public void configure(WebAppContext context) throws Exception
     @Override
     public void deconfigure(WebAppContext context) throws Exception
     {
-        //if we're not persisting the temp dir contents delete it
-        if (!context.isPersistTempDirectory() && context.getTempDirectory() != null && context.getTempDirectory().exists())
+        File tempDirectory = context.getTempDirectory();
+
+        // if we're not persisting the temp dir contents delete it
+        if (!context.isPersistTempDirectory() && tempDirectory != null && tempDirectory.exists())
         {
             IO.delete(context.getTempDirectory());
         }
@@ -504,13 +506,15 @@ public void makeTempDirectory(File parent, WebAppContext context)
             //if it is to be persisted, make sure it will be the same name
             //by not using File.createTempFile, which appends random digits
             tmpDir = new File(parent, temp);
+            configureTempDirectory(tmpDir, context);
         }
         else
         {
-            //ensure file will always be unique by appending random digits
+            // ensure dir will always be unique by having classlib generate random path name
             tmpDir = Files.createTempDirectory(parent.toPath(), temp).toFile();
+            tmpDir.deleteOnExit();
+            ensureTempDirUsable(tmpDir);
         }
-        configureTempDirectory(tmpDir, context);
 
         if (LOG.isDebugEnabled())
             LOG.debug("Set temp dir " + tmpDir);
@@ -522,6 +526,12 @@ public void configureTempDirectory(File dir, WebAppContext context)
         if (dir == null)
             throw new IllegalArgumentException("Null temp dir");
 
+        // if dir exists and we don't want it persisted, delete it
+        if (!context.isPersistTempDirectory() && dir.exists() && !IO.delete(dir))
+        {
+            throw new IllegalStateException("Failed to delete temp dir " + dir);
+        }
+
         // if it doesn't exist make it
         if (!dir.exists())
         {
@@ -531,6 +541,14 @@ public void configureTempDirectory(File dir, WebAppContext context)
             }
         }
 
+        if (!context.isPersistTempDirectory())
+            dir.deleteOnExit();
+
+        ensureTempDirUsable(dir);
+    }
+
+    private void ensureTempDirUsable(File dir)
+    {
         // is it useable
         if (!dir.canWrite() || !dir.isDirectory())
             throw new IllegalStateException("Temp dir " + dir + " not useable: writeable=" + dir.canWrite() + ", dir=" + dir.isDirectory());