Index: src/applications/drydock/blueprint/DrydockAmazonEC2HostBlueprintImplementation.php
===================================================================
--- src/applications/drydock/blueprint/DrydockAmazonEC2HostBlueprintImplementation.php
+++ src/applications/drydock/blueprint/DrydockAmazonEC2HostBlueprintImplementation.php
@@ -814,6 +814,128 @@
       }
     }
 
+    if ($resource->getAttribute('platform') === 'windows') {
+      $drive_path = $this->getDetail('storage-path');
+      if ($drive_path[1] === ':') {
+        $drive_path = $drive_path[0].':\\';
+
+        $resource->setAttribute(
+          'aws-status',
+          pht(
+            'Waiting for lease drive "%s" to appear',
+            $drive_path));
+        $resource->save();
+
+        $last_attempt = PhabricatorTime::getNow();
+
+        while (true) {
+          try {
+            $last_attempt = PhabricatorTime::getNow();
+
+            $this->log(pht(
+              'Attempting to check lease drive \'%s\' exists on \'%s\'',
+              $drive_path,
+              $instance_id));
+
+            $ssh_future = $ssh->getExecFuture(
+              'ls %s',
+              $drive_path);
+            $ssh_future->resolvex();
+            if ($ssh_future->getWasKilledByTimeout()) {
+              throw new Exception(
+                pht('%s execution timed out.', $protocol_name));
+            }
+
+            break;
+          } catch (Exception $ex) {
+
+            $this->log(pht('%s', (string)$ex));
+
+            // Make sure the instance hasn't been terminated or shutdown while
+            // we've been trying to connect.
+            $result = $this->getAWSEC2Future()
+              ->setRawAWSQuery(
+                'DescribeInstances',
+                array(
+                  'InstanceId.0' => $instance_id,
+                ))
+              ->resolve();
+
+            $reservation = $result->reservationSet->item[0];
+            $instance = $reservation->instancesSet->item[0];
+            $instance_state = (string)$instance->instanceState->name;
+
+            $this->log(pht(
+              'Lease storage drive "%s" not yet ready; instance is in '.
+              'state \'%s\'',
+              $drive_path,
+              $instance_state));
+
+            if ($instance_state === 'shutting-down' ||
+              $instance_state === 'terminated') {
+
+              $this->log(pht(
+                'Instance has ended up in state \'%s\' while waiting '.
+                'for lease storage drive to appear',
+                $instance_state));
+
+              // Deallocate and release the public IP address if we
+              // allocated one.
+              if ($resource->getAttribute('eip-allocated')) {
+                try {
+                  $this->getAWSEC2Future()
+                    ->setRawAWSQuery(
+                      'DisassociateAddress',
+                      array(
+                        'AssociationId' =>
+                          $resource->getAttribute('eip-association-id'),
+                      ))
+                    ->resolve();
+                } catch (PhutilAWSException $ex) {}
+
+                try {
+                  $this->getAWSEC2Future()
+                    ->setRawAWSQuery(
+                      'ReleaseAddress',
+                      array(
+                        'AllocationId' =>
+                          $resource->getAttribute('eip-allocation-id'),
+                      ))
+                    ->resolve();
+                } catch (PhutilAWSException $ex) {}
+
+                $resource->setAttribute(
+                  'eip-status',
+                  'Released');
+                $resource->save();
+              }
+
+              $resource->setAttribute(
+                'aws-status',
+                'Terminated');
+              $resource->save();
+
+              throw new Exception(
+                'Allocated instance, but ended up in unexpected state \''.
+                $instance_state.'\'!');
+            } else {
+              $check_time = PhabricatorTime::getNow() - $last_attempt;
+              if ($check_time < 60) {
+                $this->log(pht(
+                  '%s connection returned too quickly, manually sleeping '.
+                  'for %d seconds to avoid a large number of AWS calls.',
+                  $protocol_name,
+                  $check_time));
+                sleep($check_time);
+              }
+            }
+
+            continue;
+          }
+        }
+      }
+    }
+
     // Update the resource into open status.
     $resource->setStatus(DrydockResourceStatus::STATUS_OPEN);
     $resource->setAttribute(