diff --git a/src/applications/drydock/blueprint/DrydockAmazonEC2HostBlueprintImplementation.php b/src/applications/drydock/blueprint/DrydockAmazonEC2HostBlueprintImplementation.php
--- a/src/applications/drydock/blueprint/DrydockAmazonEC2HostBlueprintImplementation.php
+++ b/src/applications/drydock/blueprint/DrydockAmazonEC2HostBlueprintImplementation.php
@@ -861,9 +861,17 @@
       'Releasing lease %d',
       $lease->getID()));
 
-    $cmd = $lease->getInterface('command');
     $path = $lease->getAttribute('path');
 
+    // Set the path back to null for the lease.  This ensures on Windows
+    // machines we don't change to the directory we're about to delete, because
+    // Windows implicitly locks a directory from deletion whenever there is a
+    // process with it's current working directory within that directory or
+    // any of it's sub-directories.
+    $lease->setAttribute('path', null);
+
+    $cmd = $lease->getInterface('command');
+
     try {
       $this->log(pht(
         'Removing contents of \'%s\' on host',
@@ -883,7 +891,12 @@
         'occur when files are locked by the operating system.  The exception '.
         'message was \'%s\'.',
         $ex->getMessage()));
+      return;
     }
+
+    $this->log(pht(
+      'Removed contents of \'%s\' on host successfully',
+      $path));
   }
 
   public function getType() {