diff --git a/buildman/buildcomponent.py b/buildman/buildcomponent.py
index f47de4022..9b29ad5b6 100644
--- a/buildman/buildcomponent.py
+++ b/buildman/buildcomponent.py
@@ -258,7 +258,8 @@ class BuildComponent(BaseComponent):
       worker_error = WorkerError(aex.error, aex.kwargs.get('base_error'))
 
       # Write the error to the log.
-      self._build_status.set_error(worker_error.public_message(), worker_error.extra_data())
+      self._build_status.set_error(worker_error.public_message(), worker_error.extra_data(),
+                                   internal_error=worker_error.is_internal_error())
 
       # Mark the build as completed.
       if worker_error.is_internal_error():
@@ -326,6 +327,12 @@ class BuildComponent(BaseComponent):
         with build_status as status_dict:
           status_dict['heartbeat'] = int(time.time())
 
+
+      # Mark the build item.
+      current_job = self._current_job
+      if current_job is not None:
+        self.parent_manager.job_heartbeat(current_job)
+
       # Check the heartbeat from the worker.
       LOGGER.debug('Checking heartbeat on realm %s', self.builder_realm)
       if not self._last_heartbeat:
@@ -348,7 +355,7 @@ class BuildComponent(BaseComponent):
     # manager.
     if self._current_job is not None:
       if timed_out:
-        self._build_status.set_error('Build worker timed out. Build has been requeued.')
+        self._build_status.set_error('Build worker timed out', internal_error=True)
 
       self.parent_manager.job_completed(self._current_job, BuildJobResult.INCOMPLETE, self)
       self._build_status = None
diff --git a/buildman/buildstatus.py b/buildman/buildstatus.py
index 0ce509343..68b8cd5e3 100644
--- a/buildman/buildstatus.py
+++ b/buildman/buildstatus.py
@@ -28,8 +28,11 @@ class StatusHandler(object):
   def set_command(self, command, extra_data=None):
     self._append_log_message(command, self._build_logs.COMMAND, extra_data)
 
-  def set_error(self, error_message, extra_data=None):
-    self.set_phase(BUILD_PHASE.ERROR)
+  def set_error(self, error_message, extra_data=None, internal_error=False):
+    self.set_phase(BUILD_PHASE.INTERNAL_ERROR if internal_error else BUILD_PHASE.ERROR)
+
+    extra_data = extra_data or {}
+    extra_data['internal_error'] = internal_error
     self._append_log_message(error_message, self._build_logs.ERROR, extra_data)
 
   def set_phase(self, phase, extra_data=None):
diff --git a/buildman/manager/basemanager.py b/buildman/manager/basemanager.py
index 1de6e24df..f66054c45 100644
--- a/buildman/manager/basemanager.py
+++ b/buildman/manager/basemanager.py
@@ -1,10 +1,23 @@
 class BaseManager(object):
   """ Base for all worker managers. """
-  def __init__(self, register_component, unregister_component, job_complete_callback):
+  def __init__(self, register_component, unregister_component, job_heartbeat_callback,
+               job_complete_callback):
     self.register_component = register_component
     self.unregister_component = unregister_component
+    self.job_heartbeat_callback = job_heartbeat_callback
     self.job_complete_callback = job_complete_callback
 
+  def job_heartbeat(self, build_job):
+    """ Method invoked to tell the manager that a job is still running. This method will be called
+        every few minutes. """
+    self.job_heartbeat_callback(build_job)
+
+  def setup_time(self):
+    """ Returns the number of seconds that the build system should wait before allowing the job
+        to be picked up again after called 'schedule'.
+    """
+    raise NotImplementedError
+
   def shutdown(self):
     """ Indicates that the build controller server is in a shutdown state and that no new jobs
         or workers should be performed. Existing workers should be cleaned up once their jobs
diff --git a/buildman/manager/enterprise.py b/buildman/manager/enterprise.py
index 584a6daf4..9abe5f3c0 100644
--- a/buildman/manager/enterprise.py
+++ b/buildman/manager/enterprise.py
@@ -36,6 +36,11 @@ class EnterpriseManager(BaseManager):
     # production, build workers in enterprise are long-lived and register dynamically.
     self.register_component(REGISTRATION_REALM, DynamicRegistrationComponent)
 
+  def setup_time(self):
+    # Builders are already registered, so the setup time should be essentially instant. We therefore
+    # only return a minute here.
+    return 60
+
   def add_build_component(self):
     """ Adds a new build component for an Enterprise Registry. """
     # Generate a new unique realm ID for the build worker.
diff --git a/buildman/server.py b/buildman/server.py
index 0e2d7e050..fd5d4f409 100644
--- a/buildman/server.py
+++ b/buildman/server.py
@@ -9,14 +9,17 @@ from aiowsgi import create_server as create_wsgi_server
 from flask import Flask
 from threading import Event
 from trollius.coroutines import From
+from datetime import datetime, timedelta
 
 from buildman.buildjob import BuildJob, BuildJobLoadException
+from data.queue import WorkQueue
 
 LOGGER = logging.getLogger(__name__)
 
 WORK_CHECK_TIMEOUT = 10
 TIMEOUT_PERIOD_MINUTES = 20
-RESERVATION_SECONDS = (TIMEOUT_PERIOD_MINUTES + 5) * 60
+JOB_TIMEOUT_SECONDS = 300
+MINIMUM_JOB_EXTENSION = timedelta(minutes=2)
 
 class BuildJobResult(object):
   """ Build job result enum """
@@ -42,6 +45,7 @@ class BuilderServer(object):
     self._lifecycle_manager = lifecycle_manager_klass(
         self._register_component,
         self._unregister_component,
+        self._job_heartbeat,
         self._job_complete
     )
 
@@ -107,6 +111,10 @@ class BuilderServer(object):
     self._current_components.remove(component)
     self._session_factory.remove(component)
 
+  def _job_heartbeat(self, build_job):
+    WorkQueue.extend_processing(build_job.job_item(), seconds_from_now=JOB_TIMEOUT_SECONDS,
+                                retry_count=1, minimum_extension=MINIMUM_JOB_EXTENSION)
+
   def _job_complete(self, build_job, job_status):
     if job_status == BuildJobResult.INCOMPLETE:
       self._queue.incomplete(build_job.job_item(), restore_retry=True, retry_after=30)
@@ -126,7 +134,7 @@ class BuilderServer(object):
   def _work_checker(self):
     while self._current_status == 'running':
       LOGGER.debug('Checking for more work')
-      job_item = self._queue.get(processing_time=RESERVATION_SECONDS)
+      job_item = self._queue.get(processing_time=self._lifecycle_manager.setup_time())
       if job_item is None:
         LOGGER.debug('No additional work found. Going to sleep for %s seconds', WORK_CHECK_TIMEOUT)
         yield From(trollius.sleep(WORK_CHECK_TIMEOUT))
diff --git a/buildman/workererror.py b/buildman/workererror.py
index c5a5adbd0..8271976e4 100644
--- a/buildman/workererror.py
+++ b/buildman/workererror.py
@@ -73,9 +73,6 @@ class WorkerError(object):
     if handler.get('show_base_error', False) and self._base_message:
       message = message + ': ' + self._base_message
 
-    if handler.get('is_internal', False):
-      message = message + '\nThe build will be retried shortly'
-
     return message
 
   def extra_data(self):
diff --git a/data/database.py b/data/database.py
index 6562e1f63..e8874f692 100644
--- a/data/database.py
+++ b/data/database.py
@@ -370,6 +370,7 @@ class RepositoryTag(BaseModel):
 class BUILD_PHASE(object):
   """ Build phases enum """
   ERROR = 'error'
+  INTERNAL_ERROR = 'internalerror'
   UNPACKING = 'unpacking'
   PULLING = 'pulling'
   BUILDING = 'building'
diff --git a/data/queue.py b/data/queue.py
index 548ee380c..203d31eeb 100644
--- a/data/queue.py
+++ b/data/queue.py
@@ -120,10 +120,14 @@ class WorkQueue(object):
       self._currently_processing = False
 
   @staticmethod
-  def extend_processing(queue_item, seconds_from_now):
+  def extend_processing(queue_item, seconds_from_now, retry_count=None,
+                        minimum_extension=MINIMUM_EXTENSION):
     new_expiration = datetime.utcnow() + timedelta(seconds=seconds_from_now)
 
     # Only actually write the new expiration to the db if it moves the expiration some minimum
-    if new_expiration - queue_item.processing_expires > MINIMUM_EXTENSION:
+    if new_expiration - queue_item.processing_expires > minimum_extension:
+      if retry_count is not None:
+        queue_item.retries_remaining = retry_count
+
       queue_item.processing_expires = new_expiration
       queue_item.save()
diff --git a/endpoints/api/build.py b/endpoints/api/build.py
index adf6f43ec..2af1e0c8b 100644
--- a/endpoints/api/build.py
+++ b/endpoints/api/build.py
@@ -1,5 +1,7 @@
 import logging
 import json
+import time
+import datetime
 
 from flask import request, redirect
 
@@ -9,7 +11,7 @@ from endpoints.api import (RepositoryParamResource, parse_args, query_param, nic
                            ApiResource, internal_only, format_date, api, Unauthorized, NotFound)
 from endpoints.common import start_build
 from endpoints.trigger import BuildTrigger
-from data import model
+from data import model, database
 from auth.auth_context import get_authenticated_user
 from auth.permissions import ModifyRepositoryPermission, AdministerOrganizationPermission
 from data.buildlogs import BuildStatusRetrievalError
@@ -65,6 +67,13 @@ def build_status_view(build_obj, can_write=False):
     status = {}
     phase = 'cannot_load'
 
+  # If the status contains a heartbeat, then check to see if has been written in the last few
+  # minutes. If not, then the build timed out.
+  if status is not None and 'heartbeat' in status and status['heartbeat']:
+    heartbeat = datetime.datetime.fromtimestamp(status['heartbeat'])
+    if datetime.datetime.now() - heartbeat > datetime.timedelta(minutes=1):
+      phase = database.BUILD_PHASE.INTERNAL_ERROR
+
   logger.debug('Can write: %s job_config: %s', can_write, build_obj.job_config)
   resp = {
     'id': build_obj.uuid,
diff --git a/static/css/quay.css b/static/css/quay.css
index 1065fa586..2a2f80136 100644
--- a/static/css/quay.css
+++ b/static/css/quay.css
@@ -864,6 +864,10 @@ i.toggle-icon:hover {
   background-color: red;
 }
 
+.phase-icon.internalerror {
+  background-color: #DFFF00;
+}
+
 .phase-icon.waiting, .phase-icon.unpacking, .phase-icon.starting, .phase-icon.initializing {
   background-color: #ddd;
 }
diff --git a/static/directives/build-log-error.html b/static/directives/build-log-error.html
index 13b399bb9..c012a623f 100644
--- a/static/directives/build-log-error.html
+++ b/static/directives/build-log-error.html
@@ -9,7 +9,6 @@
     </span>
   </span>
 
-  
   <div class="alert alert-danger" ng-if="error.message == 'HTTP code: 403' && getLocalPullInfo().isLocal">
     <div ng-if="getLocalPullInfo().login">
       Note: The credentials <b>{{ getLocalPullInfo().login.username }}</b> for registry <b>{{ getLocalPullInfo().login.registry }}</b> cannot
diff --git a/static/js/app.js b/static/js/app.js
index 1f5d53574..3440468d4 100644
--- a/static/js/app.js
+++ b/static/js/app.js
@@ -4746,6 +4746,11 @@ quayApp.directive('buildLogError', function () {
       'entries': '=entries'
     },
     controller: function($scope, $element, Config) {
+      $scope.isInternalError = function() {
+        var entry = $scope.entries[$scope.entries.length - 1];
+        return entry && entry.data && entry.data['internal_error'];
+      };
+
       $scope.getLocalPullInfo = function() {
         if ($scope.entries.__localpull !== undefined) {
           return $scope.entries.__localpull;
@@ -5690,6 +5695,9 @@ quayApp.directive('buildMessage', function () {
           
           case 'error':
             return 'Dockerfile build failed';
+
+          case 'internalerror':
+            return 'A system error occurred while building - Will be retried shortly';
         }
       };
     }
diff --git a/static/js/controllers.js b/static/js/controllers.js
index 07041ae7a..6a4051e50 100644
--- a/static/js/controllers.js
+++ b/static/js/controllers.js
@@ -1238,7 +1238,7 @@ function RepoBuildCtrl($scope, Restangular, ApiService, $routeParams, $rootScope
 
     ApiService.getRepoBuildStatus(null, params, true).then(function(resp) {
       if (build != $scope.currentBuild) { callback(false); return; }
-      
+
       // Note: We use extend here rather than replacing as Angular is depending on the
       // root build object to remain the same object.
       var matchingBuilds = $.grep($scope.builds, function(elem) {