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
@@ -59,6 +59,11 @@
     DrydockResource $resource,
     DrydockLease $lease) {
 
+    // Allow other workers to start leasing against this.
+    $resource
+      ->setStatus(DrydockResourceStatus::STATUS_PENDING)
+      ->save();
+
     // We need to retrieve this as we need to use it for both importing the
     // key and looking up the ID for the resource attributes.
     $credential = id(new PassphraseCredentialQuery())
@@ -266,13 +271,28 @@
         $resource->setAttribute('eip-status', 'Associating Elastic IP');
         $resource->save();
 
-        $result = $this->getAWSEC2Future()
-          ->setRawAWSQuery(
-            'AssociateAddress',
-            array(
-              'InstanceId' => $instance_id,
-              'AllocationId' => $allocation_id,))
-          ->resolve();
+        while (true) {
+          try {
+            $result = $this->getAWSEC2Future()
+              ->setRawAWSQuery(
+                'AssociateAddress',
+                array(
+                  'InstanceId' => $instance_id,
+                  'AllocationId' => $allocation_id,))
+              ->resolve();
+            break;
+          } catch (PhutilAWSException $exx) {
+            if (substr_count(
+              $exx->getMessage(),
+              'InvalidAllocationID.NotFound') > 0) {
+              // AWS eventual consistency.  Wait a little while.
+              sleep(5);
+              continue;
+            } else {
+              throw $exx;
+            }
+          }
+        }
 
         $association_id = (string)$result->associationId;
 
@@ -349,6 +369,7 @@
         'credential' => $resource->getAttribute('credential'),
         'platform' => $resource->getAttribute('platform'),));
     $ssh->setConnectTimeout(60);
+    $ssh->setExecTimeout(60);
 
     $resource->setAttribute(
       'aws-status',
@@ -357,7 +378,12 @@
 
     while (true) {
       try {
-        $ssh->getExecFuture('echo "test"')->resolvex();
+        $ssh_future = $ssh->getExecFuture('echo "test"');
+        $ssh_future->resolvex();
+        if ($ssh_future->getWasKilledByTimeout()) {
+          throw new Exception('SSH execution timed out.');
+        }
+
         break;
       } catch (Exception $ex) {
 
@@ -432,6 +458,7 @@
 
     // Deallocate and release the public IP address if we allocated one.
     if ($resource->getAttribute('eip-allocated')) {
+      try {
       $this->getAWSEC2Future()
         ->setRawAWSQuery(
           'DisassociateAddress',
@@ -445,15 +472,33 @@
           array(
             'AllocationId' => $resource->getAttribute('eip-allocation-id'),))
         ->resolve();
+      } catch (PhutilAWSException $ex) {
+        if (substr_count(
+          $ex->getMessage(),
+          'InvalidAssociationID.NotFound') > 0 ||
+          substr_count($ex->getMessage(), 'InvalidAllocationID.NotFound') > 0) {
+          // TODO: Should we log this somewhere?
+        } else {
+          throw $ex;
+        }
+      }
     }
 
-    // Terminate the EC2 instance.
-    $this->getAWSEC2Future()
-      ->setRawAWSQuery(
-        'TerminateInstances',
-        array(
-          'InstanceId.0' => $resource->getAttribute('instance-id'),))
-      ->resolve();
+    try {
+      // Terminate the EC2 instance.
+      $this->getAWSEC2Future()
+        ->setRawAWSQuery(
+          'TerminateInstances',
+          array(
+            'InstanceId.0' => $resource->getAttribute('instance-id'),))
+        ->resolve();
+    } catch (PhutilAWSException $exx) {
+      if (substr_count($exx->getMessage(), 'InvalidInstanceID.NotFound') > 0) {
+        return;
+      } else {
+        throw $exx;
+      }
+    }
 
   }
 
@@ -488,7 +533,24 @@
 
     $cmd = $lease->getInterface('command');
 
-    $cmd->execx('mkdir %s', $full_path);
+    $attempts = 10;
+    while ($attempts > 0) {
+      $attempts--;
+      try {
+        if ($platform === 'windows') {
+          $cmd->execx('mkdir -Force %s', $full_path);
+        } else {
+          $cmd->execx('mkdir %s', $full_path);
+        }
+        break;
+      } catch (Exception $ex) {
+        if ($attempts == 0) {
+          throw ex;
+        }
+
+        sleep(5);
+      }
+    }
 
     $lease->setAttribute('path', $full_path);
   }
diff --git a/src/applications/drydock/controller/DrydockResourceCloseController.php b/src/applications/drydock/controller/DrydockResourceCloseController.php
--- a/src/applications/drydock/controller/DrydockResourceCloseController.php
+++ b/src/applications/drydock/controller/DrydockResourceCloseController.php
@@ -23,7 +23,8 @@
     $resource_uri = '/resource/'.$resource->getID().'/';
     $resource_uri = $this->getApplicationURI($resource_uri);
 
-    if ($resource->getStatus() != DrydockResourceStatus::STATUS_OPEN) {
+    if ($resource->getStatus() != DrydockResourceStatus::STATUS_OPEN &&
+      $resource->getStatus() != DrydockResourceStatus::STATUS_PENDING) {
       $dialog = id(new AphrontDialogView())
         ->setUser($viewer)
         ->setTitle(pht('Resource Not Open'))
diff --git a/src/applications/drydock/interface/command/DrydockSSHCommandInterface.php b/src/applications/drydock/interface/command/DrydockSSHCommandInterface.php
--- a/src/applications/drydock/interface/command/DrydockSSHCommandInterface.php
+++ b/src/applications/drydock/interface/command/DrydockSSHCommandInterface.php
@@ -4,6 +4,7 @@
 
   private $passphraseSSHKey;
   private $connectTimeout;
+  private $execTimeout;
 
   private function openCredentialsIfNotOpen() {
     if ($this->passphraseSSHKey !== null) {
@@ -31,6 +32,11 @@
     return $this;
   }
 
+  public function setExecTimeout($timeout) {
+    $this->execTimeout = $timeout;
+    return $this;
+  }
+
   public function getExecFuture($command) {
     $this->openCredentialsIfNotOpen();
 
@@ -137,6 +143,7 @@
       $this->passphraseSSHKey->getUsernameEnvelope(),
       $this->getConfig('host'),
       $full_command);
+    $future->setTimeout($this->execTimeout);
     $future->setPowershellXML($this->getConfig('platform') === 'windows');
     return $future;
   }
diff --git a/src/applications/drydock/management/DrydockManagementSSHWorkflow.php b/src/applications/drydock/management/DrydockManagementSSHWorkflow.php
--- a/src/applications/drydock/management/DrydockManagementSSHWorkflow.php
+++ b/src/applications/drydock/management/DrydockManagementSSHWorkflow.php
@@ -39,8 +39,6 @@
 
     if (!$lease) {
       $console->writeErr("Lease %d does not exist!\n", $id);
-    } else if ($lease->getStatus() != DrydockLeaseStatus::STATUS_ACTIVE) {
-      $console->writeErr("Lease %d is not 'active'!\n", $id);
     } else {
       $interface = $lease->getInterface('command');
       $future = $interface->getExecFuture('%C', $args->getArg('command'));
diff --git a/src/applications/drydock/worker/DrydockAllocatorWorker.php b/src/applications/drydock/worker/DrydockAllocatorWorker.php
--- a/src/applications/drydock/worker/DrydockAllocatorWorker.php
+++ b/src/applications/drydock/worker/DrydockAllocatorWorker.php
@@ -39,6 +39,12 @@
 
   protected function doWork() {
     $lease = $this->loadLease();
+
+    if ($lease->getStatus() != DrydockLeaseStatus::STATUS_PENDING) {
+      // We can't handle non-pending leases.
+      return;
+    }
+
     $this->logToDrydock('Allocating Lease');
 
     try {
@@ -50,7 +56,9 @@
       // and always fail after the first retry right now, so this is
       // functionally equivalent.
       $lease->reload();
-      if ($lease->getStatus() == DrydockLeaseStatus::STATUS_PENDING) {
+      if ($lease->getStatus() == DrydockLeaseStatus::STATUS_PENDING ||
+        $lease->getStatus() == DrydockLeaseStatus::STATUS_ACQUIRING) {
+
         $lease->setStatus(DrydockLeaseStatus::STATUS_BROKEN);
         $lease->save();
       }
diff --git a/src/applications/harbormaster/step/HarbormasterLeaseHostBuildStepImplementation.php b/src/applications/harbormaster/step/HarbormasterLeaseHostBuildStepImplementation.php
--- a/src/applications/harbormaster/step/HarbormasterLeaseHostBuildStepImplementation.php
+++ b/src/applications/harbormaster/step/HarbormasterLeaseHostBuildStepImplementation.php
@@ -29,11 +29,6 @@
         ) + $custom_attributes)
       ->queueForActivation();
 
-    // Wait until the lease is fulfilled.
-    // TODO: This will throw an exception if the lease can't be fulfilled;
-    // we should treat that as build failure not build error.
-    $lease->waitUntilActive();
-
     // Create the associated artifact.
     $artifact = $build->createArtifact(
       $build_target,
@@ -43,6 +38,11 @@
       'drydock-lease' => $lease->getID(),
     ));
     $artifact->save();
+
+    // Wait until the lease is fulfilled.
+    // TODO: This will throw an exception if the lease can't be fulfilled;
+    // we should treat that as build failure not build error.
+    $lease->waitUntilActive();
   }
 
   public function getArtifactOutputs() {
diff --git a/src/applications/harbormaster/storage/build/HarbormasterBuildArtifact.php b/src/applications/harbormaster/storage/build/HarbormasterBuildArtifact.php
--- a/src/applications/harbormaster/storage/build/HarbormasterBuildArtifact.php
+++ b/src/applications/harbormaster/storage/build/HarbormasterBuildArtifact.php
@@ -79,10 +79,14 @@
           ->execute();
         $lease = $leases[$data['drydock-lease']];
 
-        return id(new PHUIObjectItemView())
-          ->setObjectName(pht('Drydock Lease'))
-          ->setHeader($lease->getID())
-          ->setHref('/drydock/lease/'.$lease->getID());
+        if ($lease !== null) {
+          return id(new PHUIObjectItemView())
+            ->setObjectName(pht('Drydock Lease'))
+            ->setHeader($lease->getID())
+            ->setHref('/drydock/lease/'.$lease->getID());
+        } else {
+          return null;
+        }
       case self::TYPE_URI:
         return id(new PHUIObjectItemView())
           ->setObjectName($data['name'])
@@ -148,12 +152,25 @@
   }
 
   public function releaseDrydockLease() {
-    $lease = $this->loadDrydockLease();
+    try {
+      $lease = $this->loadDrydockLease();
+    } catch (Exception $ex) {
+      // When a resource fails to allocate correctly, the resource
+      // is deleted in the database, which will cause loadDrydockLease
+      // to throw an exception.  We ignore the exception since there's
+      // nothing to clean up if we don't have a valid lease / resource.
+      return;
+    }
+
     $resource = $lease->getResource();
     $blueprint = $resource->getBlueprint();
 
     if ($lease->isActive()) {
-      $blueprint->releaseLease($resource, $lease);
+      try {
+        $blueprint->releaseLease($resource, $lease);
+      } catch (Exception $ex) {
+        // Ignore exception
+      }
     }
   }