diff --git a/src/applications/drydock/worker/DrydockLeaseUpdateWorker.php b/src/applications/drydock/worker/DrydockLeaseUpdateWorker.php
--- a/src/applications/drydock/worker/DrydockLeaseUpdateWorker.php
+++ b/src/applications/drydock/worker/DrydockLeaseUpdateWorker.php
@@ -26,6 +26,7 @@
       $this->handleUpdate($lease);
     } catch (Exception $ex) {
       $lock->unlock();
+      $this->flushDrydockTaskQueue();
       throw $ex;
     }
 
diff --git a/src/applications/drydock/worker/DrydockResourceUpdateWorker.php b/src/applications/drydock/worker/DrydockResourceUpdateWorker.php
--- a/src/applications/drydock/worker/DrydockResourceUpdateWorker.php
+++ b/src/applications/drydock/worker/DrydockResourceUpdateWorker.php
@@ -24,6 +24,7 @@
       $this->handleUpdate($resource);
     } catch (Exception $ex) {
       $lock->unlock();
+      $this->flushDrydockTaskQueue();
       throw $ex;
     }
 
diff --git a/src/applications/drydock/worker/DrydockWorker.php b/src/applications/drydock/worker/DrydockWorker.php
--- a/src/applications/drydock/worker/DrydockWorker.php
+++ b/src/applications/drydock/worker/DrydockWorker.php
@@ -170,4 +170,30 @@
     return 15;
   }
 
+  protected function flushDrydockTaskQueue() {
+    // NOTE: By default, queued tasks are not scheduled if the current task
+    // fails. This is a good, safe default behavior. For example, it can
+    // protect us from executing side effect tasks too many times, like
+    // sending extra email.
+
+    // However, it is not the behavior we want in Drydock, because we queue
+    // followup tasks after lease and resource failures and want them to
+    // execute in order to clean things up.
+
+    // At least for now, we just explicitly flush the queue before exiting
+    // with a failure to make sure tasks get queued up properly.
+    try {
+      $this->flushTaskQueue();
+    } catch (Exception $ex) {
+      // If this fails, we want to swallow the exception so the caller throws
+      // the original error, since we're more likely to be able to understand
+      // and fix the problem if we have the original error than if we replace
+      // it with this one.
+      phlog($ex);
+    }
+
+    return $this;
+  }
+
+
 }
diff --git a/src/infrastructure/daemon/workers/PhabricatorWorker.php b/src/infrastructure/daemon/workers/PhabricatorWorker.php
--- a/src/infrastructure/daemon/workers/PhabricatorWorker.php
+++ b/src/infrastructure/daemon/workers/PhabricatorWorker.php
@@ -158,11 +158,8 @@
 
       while (true) {
         try {
-          $worker->doWork();
-          foreach ($worker->getQueuedTasks() as $queued_task) {
-            list($queued_class, $queued_data, $queued_options) = $queued_task;
-            self::scheduleTask($queued_class, $queued_data, $queued_options);
-          }
+          $worker->executeTask();
+          $worker->flushTaskQueue();
           break;
         } catch (PhabricatorWorkerYieldException $ex) {
           phlog(
@@ -236,12 +233,35 @@
    *
    * @return list<tuple<string, wild, int|null>> Queued task specifications.
    */
-  final public function getQueuedTasks() {
+  final protected function getQueuedTasks() {
     return $this->queuedTasks;
   }
 
 
   /**
+   * Schedule any queued tasks, then empty the task queue.
+   *
+   * By default, the queue is flushed only if a task succeeds. You can call
+   * this method to force the queue to flush before failing (for example, if
+   * you are using queues to improve locking behavior).
+   *
+   * @param map<string, wild> Optional default options.
+   * @return this
+   */
+  final public function flushTaskQueue($defaults = array()) {
+    foreach ($this->getQueuedTasks() as $task) {
+      list($class, $data, $options) = $task;
+
+      $options = $options + $defaults;
+
+      self::scheduleTask($class, $data, $options);
+    }
+
+    $this->queuedTasks = array();
+  }
+
+
+  /**
    * Awaken tasks that have yielded.
    *
    * Reschedules the specified tasks if they are currently queued in a yielded,
diff --git a/src/infrastructure/daemon/workers/storage/PhabricatorWorkerActiveTask.php b/src/infrastructure/daemon/workers/storage/PhabricatorWorkerActiveTask.php
--- a/src/infrastructure/daemon/workers/storage/PhabricatorWorkerActiveTask.php
+++ b/src/infrastructure/daemon/workers/storage/PhabricatorWorkerActiveTask.php
@@ -216,16 +216,11 @@
     // NOTE: If this throws, we don't want it to cause the task to fail again,
     // so execute it out here and just let the exception escape.
     if ($did_succeed) {
-      foreach ($worker->getQueuedTasks() as $task) {
-        list($class, $data, $options) = $task;
-
-        // Default the new task priority to our own priority.
-        $options = $options + array(
-          'priority' => (int)$this->getPriority(),
-        );
-
-        PhabricatorWorker::scheduleTask($class, $data, $options);
-      }
+      // Default the new task priority to our own priority.
+      $defaults = array(
+        'priority' => (int)$this->getPriority(),
+      );
+      $worker->flushTaskQueue($defaults);
     }
 
     return $result;