diff --git a/buildman/component/buildcomponent.py b/buildman/component/buildcomponent.py
index 16887d439..31b9b70bb 100644
--- a/buildman/component/buildcomponent.py
+++ b/buildman/component/buildcomponent.py
@@ -124,12 +124,13 @@ class BuildComponent(BaseComponent):
     #   username: The username for pulling the base image (if any).
     #   password: The password for pulling the base image (if any).
 
-    subdir, dockerfile_name = self.name_and_path(build_config.get('build_subdir'))
+    # TODO: Charlie Tuesday, March 28, 2017 come back and clean up build_subdir.
+    dockerfile_path = os.path.relpath(build_config.get('build_subdir'), build_config.get('context'))
 
     build_arguments = {
       'build_package': build_job.get_build_package_url(self.user_files),
-      'sub_directory': subdir,
-      'dockerfile_name': dockerfile_name,
+      'context': build_config.get('context'),
+      'dockerfile_path': dockerfile_path,
       'repository': repository_name,
       'registry': self.registry_hostname,
       'pull_token': build_job.repo_build.access_token.code,
diff --git a/buildtrigger/basehandler.py b/buildtrigger/basehandler.py
index a929ead8b..f7491e97d 100644
--- a/buildtrigger/basehandler.py
+++ b/buildtrigger/basehandler.py
@@ -1,3 +1,4 @@
+import os
 from abc import ABCMeta, abstractmethod
 from jsonschema import validate
 from six import add_metaclass
@@ -290,7 +291,7 @@ class BuildTriggerHandler(object):
   def get_dockerfile_path(self):
     """ Returns the normalized path to the Dockerfile found in the subdirectory
         in the config. """
-    dockerfile_path = self.config.get('subdir') or 'Dockerfile'
+    dockerfile_path = self.config.get('dockerfile_path') or 'Dockerfile'
     if dockerfile_path[0] == '/':
       dockerfile_path = dockerfile_path[1:]
     return dockerfile_path
@@ -303,10 +304,11 @@ class BuildTriggerHandler(object):
     ref = metadata.get('ref', None)
     commit_sha = metadata['commit']
     default_branch = metadata.get('default_branch', None)
-
     prepared = PreparedBuild(self.trigger)
     prepared.name_from_sha(commit_sha)
-    prepared.subdirectory = config.get('subdir', None)
+    # TODO: Charlie Tuesday, March 28, 2017 come back and clean up subdirectory.
+    prepared.subdirectory = config.get('dockerfile_path', None)
+    prepared.context = config.get('context', None)
     prepared.is_manual = is_manual
     prepared.metadata = metadata
 
@@ -327,3 +329,28 @@ class BuildTriggerHandler(object):
     namespaces = list(namespaces_dict.values())
     validate(namespaces, NAMESPACES_SCHEMA)
     return namespaces
+
+  @classmethod
+  def get_parent_directory_mappings(cls, dockerfile_path, current_paths=None):
+    """ Returns a map of dockerfile_paths to it's possible contexts. """
+    if dockerfile_path == "":
+      return {}
+
+    if dockerfile_path[0] != os.path.sep:
+      dockerfile_path = os.path.sep + dockerfile_path
+
+    dockerfile_path = os.path.normpath(dockerfile_path)
+    all_paths = set()
+    path, _ = os.path.split(dockerfile_path)
+    if path == "":
+      path = os.path.sep
+
+    all_paths.add(path)
+    for i in range(1, len(path.split(os.path.sep))):
+      path, _ = os.path.split(path)
+      all_paths.add(path)
+
+    if current_paths:
+      return dict({dockerfile_path: list(all_paths)}, **current_paths)
+
+    return {dockerfile_path: list(all_paths)}
diff --git a/buildtrigger/githubhandler.py b/buildtrigger/githubhandler.py
index d5ec45b73..78ffe580a 100644
--- a/buildtrigger/githubhandler.py
+++ b/buildtrigger/githubhandler.py
@@ -371,17 +371,22 @@ class GithubBuildTrigger(BuildTriggerHandler):
       raise RepositoryReadException(message)
 
     path = self.get_dockerfile_path()
-    if not path or not self.filename_is_dockerfile(os.path.basename(path)):
+    if not path:
       return None
 
     try:
       file_info = repo.get_file_contents(path)
-    except GithubException as ghe:
+    # TypeError is needed because directory inputs cause a TypeError
+    except (GithubException, TypeError) as ghe:
+      logger.error("got error from trying to find github file %s" % ghe)
       return None
 
     if file_info is None:
       return None
 
+    if isinstance(file_info, list):
+      return None
+
     content = file_info.content
     if file_info.encoding == 'base64':
       content = base64.b64decode(content)
diff --git a/buildtrigger/test/bitbucketmock.py b/buildtrigger/test/bitbucketmock.py
index c53f4a57f..83791bbaa 100644
--- a/buildtrigger/test/bitbucketmock.py
+++ b/buildtrigger/test/bitbucketmock.py
@@ -4,11 +4,11 @@ from mock import Mock
 from buildtrigger.bitbuckethandler import BitbucketBuildTrigger
 from util.morecollections import AttrDict
 
-def get_bitbucket_trigger(subdir=''):
+def get_bitbucket_trigger(dockerfile_path=''):
   trigger_obj = AttrDict(dict(auth_token='foobar', id='sometrigger'))
   trigger = BitbucketBuildTrigger(trigger_obj, {
     'build_source': 'foo/bar',
-    'subdir': subdir,
+    'dockerfile_path': dockerfile_path,
     'username': 'knownuser'
   })
 
diff --git a/buildtrigger/test/githubmock.py b/buildtrigger/test/githubmock.py
index 295956614..f1c71e9c8 100644
--- a/buildtrigger/test/githubmock.py
+++ b/buildtrigger/test/githubmock.py
@@ -6,9 +6,9 @@ from github import GithubException
 from buildtrigger.githubhandler import GithubBuildTrigger
 from util.morecollections import AttrDict
 
-def get_github_trigger(subdir=''):
+def get_github_trigger(dockerfile_path=''):
   trigger_obj = AttrDict(dict(auth_token='foobar', id='sometrigger'))
-  trigger = GithubBuildTrigger(trigger_obj, {'build_source': 'foo', 'subdir': subdir})
+  trigger = GithubBuildTrigger(trigger_obj, {'build_source': 'foo', 'dockerfile_path': dockerfile_path})
   trigger._get_client = get_mock_github
   return trigger
 
diff --git a/buildtrigger/test/gitlabmock.py b/buildtrigger/test/gitlabmock.py
index c7d4a5865..2739a539f 100644
--- a/buildtrigger/test/gitlabmock.py
+++ b/buildtrigger/test/gitlabmock.py
@@ -4,11 +4,11 @@ from mock import Mock
 from buildtrigger.gitlabhandler import GitLabBuildTrigger
 from util.morecollections import AttrDict
 
-def get_gitlab_trigger(subdir=''):
+def get_gitlab_trigger(dockerfile_path=''):
   trigger_obj = AttrDict(dict(auth_token='foobar', id='sometrigger'))
   trigger = GitLabBuildTrigger(trigger_obj, {
     'build_source': 'foo/bar',
-    'subdir': subdir,
+    'dockerfile_path': dockerfile_path,
     'username': 'knownuser'
   })
 
diff --git a/buildtrigger/test/test_basehandler.py b/buildtrigger/test/test_basehandler.py
index 5bf95c41b..7162c2535 100644
--- a/buildtrigger/test/test_basehandler.py
+++ b/buildtrigger/test/test_basehandler.py
@@ -13,3 +13,43 @@ from buildtrigger.basehandler import BuildTriggerHandler
 ])
 def test_path_is_dockerfile(input, output):
   assert BuildTriggerHandler.filename_is_dockerfile(input) == output
+
+
+@pytest.mark.parametrize('input,output', [
+  ("", {}),
+  ("/a", {"/a": ["/"]}),
+  ("a", {"/a": ["/"]}),
+  ("/b/a", {"/b/a": ["/b", "/"]}),
+  ("b/a", {"/b/a": ["/b", "/"]}),
+  ("/c/b/a", {"/c/b/a": ["/c/b", "/c", "/"]}),
+  ("/a//b//c", {"/a/b/c": ["/", "/a", "/a/b"]}),
+  ("/a", {"/a": ["/"]}),
+])
+def test_subdir_path_map_no_previous(input, output):
+  actual_mapping = BuildTriggerHandler.get_parent_directory_mappings(input)
+  for key in actual_mapping:
+    value = actual_mapping[key]
+    actual_mapping[key] = value.sort()
+  for key in output:
+    value = output[key]
+    output[key] = value.sort()
+
+  assert actual_mapping == output
+
+
+@pytest.mark.parametrize('new_path,original_dictionary,output', [
+  ("/a", {}, {"/a": ["/"]}),
+  ("b", {"/a": ["some_path", "another_path"]}, {"/a": ["some_path", "another_path"], "/b": ["/"]}),
+  ("/a/b/c/d", {"/e": ["some_path", "another_path"]},
+   {"/e": ["some_path", "another_path"], "/a/b/c/d": ["/", "/a", "/a/b", "/a/b/c"]}),
+])
+def test_subdir_path_map(new_path, original_dictionary, output):
+  actual_mapping = BuildTriggerHandler.get_parent_directory_mappings(new_path, original_dictionary)
+  for key in actual_mapping:
+    value = actual_mapping[key]
+    actual_mapping[key] = value.sort()
+  for key in output:
+    value = output[key]
+    output[key] = value.sort()
+
+  assert actual_mapping == output
diff --git a/buildtrigger/test/test_bitbuckethandler.py b/buildtrigger/test/test_bitbuckethandler.py
index 320a18906..c4ebb4ac7 100644
--- a/buildtrigger/test/test_bitbuckethandler.py
+++ b/buildtrigger/test/test_bitbuckethandler.py
@@ -16,13 +16,13 @@ def test_list_build_subdirs(bitbucket_trigger):
   assert bitbucket_trigger.list_build_subdirs() == ["/Dockerfile"]
 
 
-@pytest.mark.parametrize('subdir, contents', [
+@pytest.mark.parametrize('dockerfile_path, contents', [
   ('/Dockerfile', 'hello world'),
   ('somesubdir/Dockerfile', 'hi universe'),
   ('unknownpath', None),
 ])
-def test_load_dockerfile_contents(subdir, contents):
-  trigger = get_bitbucket_trigger(subdir)
+def test_load_dockerfile_contents(dockerfile_path, contents):
+  trigger = get_bitbucket_trigger(dockerfile_path)
   assert trigger.load_dockerfile_contents() == contents
 
 
diff --git a/buildtrigger/test/test_githubhandler.py b/buildtrigger/test/test_githubhandler.py
index db236048c..3d8ac2763 100644
--- a/buildtrigger/test/test_githubhandler.py
+++ b/buildtrigger/test/test_githubhandler.py
@@ -68,13 +68,13 @@ def test_handle_trigger_request(github_trigger, payload, expected_error, expecte
     assert isinstance(github_trigger.handle_trigger_request(request), PreparedBuild)
 
 
-@pytest.mark.parametrize('subdir, contents', [
+@pytest.mark.parametrize('dockerfile_path, contents', [
   ('/Dockerfile', 'hello world'),
   ('somesubdir/Dockerfile', 'hi universe'),
   ('unknownpath', None),
 ])
-def test_load_dockerfile_contents(subdir, contents):
-  trigger = get_github_trigger(subdir)
+def test_load_dockerfile_contents(dockerfile_path, contents):
+  trigger = get_github_trigger(dockerfile_path)
   assert trigger.load_dockerfile_contents() == contents
 
 
diff --git a/buildtrigger/test/test_gitlabhandler.py b/buildtrigger/test/test_gitlabhandler.py
index a74f5fea2..6f6555769 100644
--- a/buildtrigger/test/test_gitlabhandler.py
+++ b/buildtrigger/test/test_gitlabhandler.py
@@ -16,13 +16,13 @@ def test_list_build_subdirs(gitlab_trigger):
   assert gitlab_trigger.list_build_subdirs() == ['/Dockerfile']
 
 
-@pytest.mark.parametrize('subdir, contents', [
+@pytest.mark.parametrize('dockerfile_path, contents', [
   ('/Dockerfile', 'hello world'),
   ('somesubdir/Dockerfile', 'hi universe'),
   ('unknownpath', None),
 ])
-def test_load_dockerfile_contents(subdir, contents):
-  trigger = get_gitlab_trigger(subdir)
+def test_load_dockerfile_contents(dockerfile_path, contents):
+  trigger = get_gitlab_trigger(dockerfile_path)
   assert trigger.load_dockerfile_contents() == contents
 
 
diff --git a/data/migrations/versions/a6c463dfb9fe_back_fill_build_expand_config.py b/data/migrations/versions/a6c463dfb9fe_back_fill_build_expand_config.py
new file mode 100644
index 000000000..44701f959
--- /dev/null
+++ b/data/migrations/versions/a6c463dfb9fe_back_fill_build_expand_config.py
@@ -0,0 +1,85 @@
+"""back fill build expand_config
+
+Revision ID: a6c463dfb9fe
+Revises: e2894a3a3c19
+Create Date: 2017-03-17 10:00:19.739858
+
+"""
+
+# revision identifiers, used by Alembic.
+import json
+import os
+
+from data.database import RepositoryBuildTrigger
+
+revision = 'a6c463dfb9fe'
+down_revision = 'e2894a3a3c19'
+
+from alembic import op
+
+
+def upgrade(tables):
+  repostioryBuildTriggers = RepositoryBuildTrigger.select()
+  for repositoryBuildTrigger in repostioryBuildTriggers:
+    config = json.loads(repositoryBuildTrigger.config)
+    repositoryBuildTrigger.config = json.dumps(get_config_expand(config))
+
+
+def downgrade(tables):
+  repostioryBuildTriggers = RepositoryBuildTrigger.select()
+  for repositoryBuildTrigger in repostioryBuildTriggers:
+    config = json.loads(repositoryBuildTrigger.config)
+    repositoryBuildTrigger.config = json.dumps(get_config_expand(config))
+
+
+def create_context(current_subdir):
+  if current_subdir == "":
+    current_subdir = os.path.sep + current_subdir
+
+  if current_subdir[len(current_subdir) - 1] != os.path.sep:
+    current_subdir += os.path.sep
+
+  context, _ = os.path.split(current_subdir)
+  return context
+
+
+def create_dockerfile_path(current_subdir):
+  if current_subdir == "":
+    current_subdir = os.path.sep + current_subdir
+
+  if current_subdir[len(current_subdir) - 1] != os.path.sep:
+    current_subdir += os.path.sep
+
+  return current_subdir + "Dockerfile"
+
+
+def get_config_expand(config):
+  """ A function to transform old records into new records """
+  if not config:
+    return config
+
+  # skip records that have been updated
+  if "context" in config or "dockerfile_path" in config:
+    return config
+
+  config_expand = {}
+  if "subdir" in config:
+    config_expand = dict(config)
+    config_expand["context"] = create_context(config["subdir"])
+    config_expand["dockerfile_path"] = create_dockerfile_path(config["subdir"])
+
+  return config_expand
+
+
+def get_config_contract(config):
+  """ A function to delete context and dockerfile_path from config """
+  if not config:
+    return config
+
+  if "context" in config:
+    del config["context"]
+
+  if "dockerfile_path" in config:
+    del config["dockerfile_path"]
+
+  return config
diff --git a/data/model/build.py b/data/model/build.py
index 605259e14..e67eaffe5 100644
--- a/data/model/build.py
+++ b/data/model/build.py
@@ -18,10 +18,14 @@ PHASES_NOT_ALLOWED_TO_CANCEL_FROM = (BUILD_PHASE.PUSHING, BUILD_PHASE.COMPLETE,
 ARCHIVABLE_BUILD_PHASES = [BUILD_PHASE.COMPLETE, BUILD_PHASE.ERROR, BUILD_PHASE.CANCELLED]
 
 
-def update_build_trigger(trigger, config, auth_token=None):
+def update_build_trigger(trigger, config, auth_token=None, write_token=None):
   trigger.config = json.dumps(_get_config_expand(config or {}))
   if auth_token is not None:
     trigger.auth_token = auth_token
+
+  if write_token is not None:
+    trigger.write_token = write_token
+
   trigger.save()
 
 
diff --git a/data/model/helpers/build_helper.py b/data/model/helpers/build_helper.py
index 7de9da254..1f5da8296 100644
--- a/data/model/helpers/build_helper.py
+++ b/data/model/helpers/build_helper.py
@@ -1,44 +1,9 @@
-import os
-
 
 def _get_config_expand(config):
   """ Get config with both context and dockerfile_path written to it """
-  if config and "subdir" in config and "context" not in config:
-    config_expand = dict(config)
-    config_expand["context"] = _create_context(config["subdir"])
-    config_expand["dockerfile_path"] = _create_dockerfile_path(config["subdir"])
-    return config_expand
-  return config or {}
+  if not config:
+    return {}
+  if 'context' in config:
+    config['subdir'] = config['context']
 
-
-def _create_context(current_subdir):
-  """ Create context from current subdir """
-  if current_subdir.endswith("Dockerfile"):
-    context, _ = os.path.split(current_subdir)
-    if context == "":
-      return os.path.sep
-
-    return context
-
-  if current_subdir == "":
-    current_subdir = os.path.sep + current_subdir
-
-  if current_subdir[len(current_subdir) - 1] != os.path.sep:
-    current_subdir += os.path.sep
-
-  context, _ = os.path.split(current_subdir)
-  return context
-
-
-def _create_dockerfile_path(current_subdir):
-  """ Create dockefile path from current subdir """
-  if current_subdir.endswith("Dockerfile"):
-    return current_subdir
-
-  if current_subdir == "":
-    current_subdir = os.path.sep + current_subdir
-
-  if current_subdir[len(current_subdir) - 1] != os.path.sep:
-    current_subdir += os.path.sep
-
-  return current_subdir + "Dockerfile"
+  return config
diff --git a/data/model/helpers/test/test_build_helper.py b/data/model/helpers/test/test_build_helper.py
index cfb792d6f..25686faff 100644
--- a/data/model/helpers/test/test_build_helper.py
+++ b/data/model/helpers/test/test_build_helper.py
@@ -4,27 +4,11 @@ from data.model.helpers.build_helper import _get_config_expand
 
 
 @pytest.mark.parametrize('org_config,expected', [
-  # Empty config
   (None, {}),
-
-  # No subdir in config
   ({}, {}),
-
-  ({"subdir": ""}, {"context": "/", "dockerfile_path": "/Dockerfile", "subdir": ""}),
-  ({"subdir": "/"}, {"context": "/", "dockerfile_path": "/Dockerfile", "subdir": "/"}),
-  ({"subdir": "/Dockerfile"}, {"context": "/", "dockerfile_path": "/Dockerfile", "subdir": "/Dockerfile"}),
-  ({"subdir": "a"}, {"context": "a", "dockerfile_path": "a/Dockerfile", "subdir": "a"}),
-  ({"subdir": "Dockerfile"}, {"context": "/", "dockerfile_path": "Dockerfile", "subdir": "Dockerfile"}),
-  ({"subdir": "server.Dockerfile"},
-   {"context": "/", "dockerfile_path": "server.Dockerfile", "subdir": "server.Dockerfile"}),
-  ({"subdir": "/a/b/Dockerfile"},
-   {"context": "/a/b", "dockerfile_path": "/a/b/Dockerfile", "subdir": "/a/b/Dockerfile"}),
-  ({"subdir": "/a/b/server.Dockerfile"},
-   {"context": "/a/b", "dockerfile_path": "/a/b/server.Dockerfile", "subdir": "/a/b/server.Dockerfile"}),
-  ({"subdir": "a/b/Dockerfile"}, {"context": "a/b", "dockerfile_path": "a/b/Dockerfile", "subdir": "a/b/Dockerfile"}),
-  ({"subdir": "a/b/server.Dockerfile"},
-   {"context": "a/b", "dockerfile_path": "a/b/server.Dockerfile", "subdir": "a/b/server.Dockerfile"}),
-  ({"subdir": "/a/b/c", "context": "slime"}, {"context": "slime", "subdir": "/a/b/c"}),
+  ({'some other key': 'some other value'}, {'some other key': 'some other value'}),
+  ({'context': 'some/context', 'dockerfile_path': 'some/context/with/Dockerfile'},
+  {'context': 'some/context', 'dockerfile_path': 'some/context/with/Dockerfile', 'subdir': 'some/context'}),
 ])
 def test_super_user_build_endpoints(org_config, expected):
   assert _get_config_expand(org_config) == expected
diff --git a/endpoints/api/build.py b/endpoints/api/build.py
index 1bb575a4f..1a0d1c89c 100644
--- a/endpoints/api/build.py
+++ b/endpoints/api/build.py
@@ -1,5 +1,5 @@
 """ Create, list, cancel and get status/logs of repository builds. """
-
+import os
 from urlparse import urlparse
 
 import logging
@@ -51,6 +51,7 @@ def user_view(user):
     'is_robot': user.robot,
   }
 
+
 def trigger_view(trigger, can_read=False, can_admin=False, for_build=False):
   if trigger and trigger.uuid:
     build_trigger = BuildTriggerHandler.get_handler(trigger)
@@ -133,6 +134,8 @@ def build_status_view(build_obj):
     'display_name': build_obj.display_name,
     'status': status or {},
     'subdirectory': job_config.get('build_subdir', ''),
+    'dockerfile_path': job_config.get('build_subdir', ''),
+    'context': job_config.get('context', ''),
     'tags': job_config.get('docker_tags', []),
     'manual_user': job_config.get('manual_user', None),
     'is_writer': can_write,
@@ -244,6 +247,7 @@ class RepositoryBuildList(RepositoryParamResource):
         raise InvalidRequest('Invalid Archive URL: Must be http or https')
 
     subdir = request_json['subdirectory'] if 'subdirectory' in request_json else ''
+    context = request_json['context'] if 'context' in request_json else os.path.dirname(subdir)
     tags = request_json.get('docker_tags', ['latest'])
     pull_robot_name = request_json.get('pull_robot', None)
 
@@ -291,9 +295,9 @@ class RepositoryBuildList(RepositoryParamResource):
     prepared.archive_url = archive_url
     prepared.tags = tags
     prepared.subdirectory = subdir
+    prepared.context = context
     prepared.is_manual = True
     prepared.metadata = {}
-
     try:
       build_request = start_build(repo, prepared, pull_robot_name=pull_robot_name)
     except MaximumBuildsQueuedException:
diff --git a/endpoints/api/test/test_trigger.py b/endpoints/api/test/test_trigger.py
new file mode 100644
index 000000000..48339c9d4
--- /dev/null
+++ b/endpoints/api/test/test_trigger.py
@@ -0,0 +1,22 @@
+import pytest
+
+from endpoints.api.trigger import is_parent
+
+
+@pytest.mark.parametrize('context,dockerfile_path,expected', [
+  ("/", "/a/b", True),
+  ("/a", "/a/b", True),
+  ("/a/b", "/a/b", False),
+  ("/a//", "/a/b", True),
+  ("/a", "/a//b/c", True),
+  ("/a//", "a/b", True),
+  ("/a/b", "a/bc/d", False),
+  ("/d", "/a/b", False),
+  ("/a/b", "/a/b.c", False),
+  ("/a/b", "/a/b/b.c", True),
+  ("", "/a/b.c", False),
+  ("/a/b", "", False),
+  ("", "", False),
+])
+def test_super_user_build_endpoints(context, dockerfile_path, expected):
+  assert is_parent(context, dockerfile_path) == expected
diff --git a/endpoints/api/trigger.py b/endpoints/api/trigger.py
index 2698bbb3b..1bb885878 100644
--- a/endpoints/api/trigger.py
+++ b/endpoints/api/trigger.py
@@ -2,17 +2,21 @@
 
 import json
 import logging
-
+from os import path
 from urllib import quote
 from urlparse import urlunparse
 
 from flask import request, url_for
 
 from app import app
+from auth.permissions import (UserAdminPermission, AdministerOrganizationPermission,
+                              ReadRepositoryPermission, AdministerRepositoryPermission)
 from buildtrigger.basehandler import BuildTriggerHandler
 from buildtrigger.triggerutil import (TriggerDeactivationException,
                                       TriggerActivationException, EmptyRepositoryException,
                                       RepositoryReadException, TriggerStartException)
+from data import model
+from data.model.build import update_build_trigger
 from endpoints.api import (RepositoryParamResource, nickname, resource, require_repo_admin,
                            log_action, request_error, query_param, parse_args, internal_only,
                            validate_json_request, api, path_param, abort,
@@ -20,12 +24,9 @@ from endpoints.api import (RepositoryParamResource, nickname, resource, require_
 from endpoints.exception import NotFound, Unauthorized, InvalidRequest
 from endpoints.api.build import build_status_view, trigger_view, RepositoryBuildStatus
 from endpoints.building import start_build, MaximumBuildsQueuedException
-from data import model
-from auth.permissions import (UserAdminPermission, AdministerOrganizationPermission,
-                              ReadRepositoryPermission, AdministerRepositoryPermission)
-from util.names import parse_robot_username
+from endpoints.exception import NotFound, Unauthorized, InvalidRequest
 from util.dockerfileparse import parse_dockerfile
-
+from util.names import parse_robot_username
 
 logger = logging.getLogger(__name__)
 
@@ -131,19 +132,25 @@ class BuildTriggerSubdirs(RepositoryParamResource):
 
       try:
         subdirs = handler.list_build_subdirs()
+        context_map = {}
+        for file in subdirs:
+          context_map = handler.get_parent_directory_mappings(file, context_map)
+
         return {
-          'subdir': ['/' + subdir for subdir in subdirs],
-          'status': 'success'
+          'dockerfile_paths': ['/' + subdir for subdir in subdirs],
+          'contextMap': context_map,
+          'status': 'success',
         }
       except EmptyRepositoryException as exc:
         return {
           'status': 'success',
-          'subdir': []
+          'contextMap': {},
+          'dockerfile_paths': [],
         }
       except RepositoryReadException as exc:
         return {
           'status': 'error',
-          'message': exc.message
+          'message': exc.message,
         }
     else:
       raise Unauthorized()
@@ -235,9 +242,7 @@ class BuildTriggerActivate(RepositoryParamResource):
         raise request_error(message=exc.message)
 
       # Save the updated config.
-      trigger.config = json.dumps(final_config)
-      trigger.write_token = write_token
-      trigger.save()
+      update_build_trigger(trigger, final_config, write_token=write_token)
 
       # Log the trigger setup.
       repo = model.repository.get_repository(namespace_name, repo_name)
@@ -343,6 +348,15 @@ class BuildTriggerAnalyze(RepositoryParamResource):
           'message': 'Could not parse the Dockerfile specified'
         }
 
+      # Check whether the dockerfile_path is correct
+      if new_config_dict.get('context'):
+        if not is_parent(new_config_dict.get('context'), new_config_dict.get('dockerfile_path')):
+          return {
+            'status': 'error',
+            'message': 'Dockerfile, %s, is not child of the context, %s.' %
+                       (new_config_dict.get('context'), new_config_dict.get('dockerfile_path'))
+          }
+
       # Default to the current namespace.
       base_namespace = namespace_name
       base_repository = None
@@ -399,6 +413,28 @@ class BuildTriggerAnalyze(RepositoryParamResource):
     raise NotFound()
 
 
+def is_parent(context, dockerfile_path):
+  """ This checks whether the context is a parent of the dockerfile_path"""
+  if context == "" or dockerfile_path == "":
+    return False
+
+  normalized_context = path.normpath(context)
+  if normalized_context[len(normalized_context) - 1] != path.sep:
+    normalized_context += path.sep
+
+  if normalized_context[0] != path.sep:
+    normalized_context = path.sep + normalized_context
+
+  normalized_subdir = path.normpath(path.dirname(dockerfile_path))
+  if normalized_subdir[0] != path.sep:
+    normalized_subdir = path.sep + normalized_subdir
+
+  if normalized_subdir[len(normalized_subdir) - 1] != path.sep:
+    normalized_subdir += path.sep
+
+  return normalized_subdir.startswith(normalized_context)
+
+
 @resource('/v1/repository/<apirepopath:repository>/trigger/<trigger_uuid>/start')
 @path_param('repository', 'The full path of the repository. e.g. namespace/name')
 @path_param('trigger_uuid', 'The UUID of the build trigger')
@@ -418,7 +454,7 @@ class ActivateBuildTrigger(RepositoryParamResource):
           'description': '(Custom Only) If specified, the ref/SHA1 used to checkout a git repository.'
         },
         'refs': {
-          'type': ['object',  'null'],
+          'type': ['object', 'null'],
           'description': '(SCM Only) If specified, the ref to build.'
         }
       },
@@ -467,6 +503,7 @@ class ActivateBuildTrigger(RepositoryParamResource):
 @path_param('trigger_uuid', 'The UUID of the build trigger')
 class TriggerBuildList(RepositoryParamResource):
   """ Resource to represent builds that were activated from the specified trigger. """
+
   @require_repo_admin
   @disallow_for_app_repositories
   @parse_args()
@@ -483,10 +520,12 @@ class TriggerBuildList(RepositoryParamResource):
 
 FIELD_VALUE_LIMIT = 30
 
+
 @resource('/v1/repository/<apirepopath:repository>/trigger/<trigger_uuid>/fields/<field_name>')
 @internal_only
 class BuildTriggerFieldValues(RepositoryParamResource):
   """ Custom verb to fetch a values list for a particular field name. """
+
   @require_repo_admin
   @disallow_for_app_repositories
   @nickname('listTriggerFieldValues')
@@ -558,13 +597,13 @@ class BuildTriggerSources(RepositoryParamResource):
       raise Unauthorized()
 
 
-
 @resource('/v1/repository/<apirepopath:repository>/trigger/<trigger_uuid>/namespaces')
 @path_param('repository', 'The full path of the repository. e.g. namespace/name')
 @path_param('trigger_uuid', 'The UUID of the build trigger')
 @internal_only
 class BuildTriggerSourceNamespaces(RepositoryParamResource):
   """ Custom verb to fetch the list of namespaces (orgs, projects, etc) for the trigger config. """
+
   @require_repo_admin
   @disallow_for_app_repositories
   @nickname('listTriggerBuildSourceNamespaces')
diff --git a/endpoints/building.py b/endpoints/building.py
index a1e17897d..8515287a1 100644
--- a/endpoints/building.py
+++ b/endpoints/building.py
@@ -54,6 +54,7 @@ def start_build(repository, prepared_build, pull_robot_name=None):
     'docker_tags': prepared_build.tags,
     'registry': host,
     'build_subdir': prepared_build.subdirectory,
+    'context': prepared_build.context,
     'trigger_metadata': prepared_build.metadata or {},
     'is_manual': prepared_build.is_manual,
     'manual_user': get_authenticated_user().username if get_authenticated_user() else None,
@@ -122,6 +123,7 @@ class PreparedBuild(object):
     self._tags = None
     self._build_name = None
     self._subdirectory = None
+    self._context = None
     self._metadata = None
     self._trigger = trigger
     self._is_manual = None
@@ -224,6 +226,20 @@ class PreparedBuild(object):
 
     self._subdirectory = value
 
+  @property
+  def context(self):
+    if self._context is None:
+      raise Exception('Missing property context')
+
+    return self._context
+
+  @context.setter
+  def context(self, value):
+    if self._context:
+      raise Exception('Property context already set')
+
+    self._context = value
+
   @property
   def metadata(self):
     if self._metadata is None:
diff --git a/initdb.py b/initdb.py
index 0a284ae4a..03bb9131c 100644
--- a/initdb.py
+++ b/initdb.py
@@ -605,6 +605,8 @@ def populate_database(minimal=False, with_storage=False):
   trigger.config = json.dumps({
     'build_source': 'jakedt/testconnect',
     'subdir': '',
+    'dockerfile_path': 'Dockerfile',
+    'context': '/',
   })
   trigger.save()
 
diff --git a/static/directives/repo-view/repo-panel-builds.html b/static/directives/repo-view/repo-panel-builds.html
index 327846002..f59fb8361 100644
--- a/static/directives/repo-view/repo-panel-builds.html
+++ b/static/directives/repo-view/repo-panel-builds.html
@@ -119,6 +119,7 @@
           <thead>
             <td>Trigger Name</td>
             <td>Dockerfile Location</td>
+            <td>Context Location</td>
             <td>Branches/Tags</td>
             <td>Pull Robot</td>
             <td class="options-col"></td>
@@ -133,7 +134,8 @@
 
           <tr ng-repeat="trigger in triggers | filter:{'is_active':true}">
             <td><div class="trigger-description" trigger="trigger"></div></td>
-            <td>{{ trigger.config.subdir || '/' }}</td>
+            <td>{{ trigger.config.dockerfile_path || '/Dockerfile' }}</td>
+            <td>{{ trigger.config.context  || '/' }}</td>
             <td>{{ trigger.config.branchtag_regex || 'All' }}</td>
             <td>
               <span class="entity-reference" entity="trigger.pull_robot" ng-if="trigger.pull_robot"></span>
diff --git a/static/js/directives/ui/context-path-select/context-path-select.component.html b/static/js/directives/ui/context-path-select/context-path-select.component.html
new file mode 100644
index 000000000..dac40463a
--- /dev/null
+++ b/static/js/directives/ui/context-path-select/context-path-select.component.html
@@ -0,0 +1,33 @@
+<div class="context-path-select-element">
+  <div class="dropdown-select" placeholder="'Enter a docker context'"
+       selected-item="$ctrl.selectedContext"
+       lookahead-items="$ctrl.contexts"
+       handle-input="$ctrl.setContext(input)"
+       handle-item-selected="$ctrl.setSelectedContext(datum.value)"
+       allow-custom-input="true"
+       hide-dropdown="$ctrl.contexts.length <= 0">
+    <!-- Icons -->
+    <i class="dropdown-select-icon none-icon fa fa-folder-o fa-lg"
+       ng-show="$ctrl.isUnknownContext"></i>
+    <i class="dropdown-select-icon none-icon fa fa-folder fa-lg" style="color: black;"
+       ng-show="!$ctrl.isUnknownContext"></i>
+    <i class="dropdown-select-icon fa fa-folder fa-lg"></i>
+
+    <!-- Dropdown menu -->
+    <ul class="dropdown-select-menu pull-right" role="menu">
+      <li ng-repeat="context in $ctrl.contexts">
+        <a ng-click="$ctrl.setSelectedContext(context)"
+           ng-if="context">
+          <i class="fa fa-folder fa-lg"></i> {{ context }}
+        </a>
+      </li>
+    </ul>
+  </div>
+
+  <div style="padding: 10px">
+    <div class="co-alert co-alert-danger"
+         ng-show="!$ctrl.isValidContext && $ctrl.currentContext">
+      Path is an invalid context.
+    </div>
+  </div>
+</div>
diff --git a/static/js/directives/ui/context-path-select/context-path-select.component.spec.ts b/static/js/directives/ui/context-path-select/context-path-select.component.spec.ts
new file mode 100644
index 000000000..033ce4945
--- /dev/null
+++ b/static/js/directives/ui/context-path-select/context-path-select.component.spec.ts
@@ -0,0 +1,87 @@
+import { ContextPathSelectComponent } from './context-path-select.component';
+
+
+describe("ContextPathSelectComponent", () => {
+  var component: ContextPathSelectComponent;
+  var currentContext: string;
+  var isValidContext: boolean;
+  var contexts: string[];
+
+  beforeEach(() => {
+    component = new ContextPathSelectComponent();
+    currentContext = '/';
+    isValidContext = false;
+    contexts = ['/'];
+    component.currentContext = currentContext;
+    component.isValidContext = isValidContext;
+    component.contexts = contexts;
+  });
+
+  describe("$onChanges", () => {
+
+    it("sets valid context flag to true if current context is valid", () => {
+      component.$onChanges({});
+
+      expect(component.isValidContext).toBe(true);
+    });
+
+    it("sets valid context flag to false if current context is invalid", () => {
+      component.currentContext = "asdfdsf";
+      component.$onChanges({});
+
+      expect(component.isValidContext).toBe(false);
+    });
+  });
+
+  describe("setcontext", () => {
+    var newContext: string;
+
+    beforeEach(() => {
+      newContext = '/conf';
+    });
+
+    it("sets current context to given context", () => {
+      component.setContext(newContext);
+
+      expect(component.currentContext).toEqual(newContext);
+    });
+
+    it("sets valid context flag to true if given context is valid", () => {
+      component.setContext(newContext);
+
+      expect(component.isValidContext).toBe(true);
+    });
+
+    it("sets valid context flag to false if given context is invalid", () => {
+      component.setContext("asdfsadfs");
+
+      expect(component.isValidContext).toBe(false);
+    });
+  });
+
+  describe("setCurrentcontext", () => {
+    var context: string;
+
+    beforeEach(() => {
+      context = '/conf';
+    });
+
+    it("sets current context to given context", () => {
+      component.setSelectedContext(context);
+
+      expect(component.currentContext).toEqual(context);
+    });
+
+    it("sets valid context flag to true if given context is valid", () => {
+      component.setSelectedContext(context);
+
+      expect(component.isValidContext).toBe(true);
+    });
+
+    it("sets valid context flag to false if given context is invalid", () => {
+      component.setSelectedContext("a;lskjdf;ldsa");
+
+      expect(component.isValidContext).toBe(false);
+    });
+  });
+});
\ No newline at end of file
diff --git a/static/js/directives/ui/context-path-select/context-path-select.component.ts b/static/js/directives/ui/context-path-select/context-path-select.component.ts
new file mode 100644
index 000000000..4d70992f6
--- /dev/null
+++ b/static/js/directives/ui/context-path-select/context-path-select.component.ts
@@ -0,0 +1,46 @@
+import { Input, Component } from 'angular-ts-decorators';
+
+
+/**
+ * A component that allows the user to select the location of the Context in their source code repository.
+ */
+@Component({
+  selector: 'contextPathSelect',
+  templateUrl: '/static/js/directives/ui/context-path-select/context-path-select.component.html'
+})
+export class ContextPathSelectComponent implements ng.IComponentController {
+
+  // FIXME: Use one-way data binding
+  @Input('=') public currentContext: string;
+  @Input('=') public isValidContext: boolean;
+  @Input('=') public contexts: string[];
+  private isUnknownContext: boolean = true;
+  private selectedContext: string | null = null;
+
+  public $onChanges(changes: ng.IOnChangesObject): void {
+    this.isValidContext = this.checkContext(this.currentContext, this.contexts);
+  }
+
+  public setContext(context: string): void {
+    this.currentContext = context;
+    this.selectedContext = null;
+    this.isValidContext = this.checkContext(context, this.contexts);
+  }
+
+  public setSelectedContext(context: string): void {
+    this.currentContext = context;
+    this.selectedContext = context;
+    this.isValidContext = this.checkContext(context, this.contexts);
+  }
+
+  private checkContext(context: string = '', contexts: string[] = []): boolean {
+    this.isUnknownContext = false;
+    var isValidContext: boolean = false;
+
+    if (context.length > 0 && context[0] === '/') {
+      isValidContext = true;
+      this.isUnknownContext = true;
+    }
+    return isValidContext;
+  }
+}
diff --git a/static/js/directives/ui/manage-trigger-githost/manage-trigger-githost.component.html b/static/js/directives/ui/manage-trigger-githost/manage-trigger-githost.component.html
index 6298cc9df..1ecc8e28d 100644
--- a/static/js/directives/ui/manage-trigger-githost/manage-trigger-githost.component.html
+++ b/static/js/directives/ui/manage-trigger-githost/manage-trigger-githost.component.html
@@ -257,9 +257,10 @@
 
         <dockerfile-path-select
           current-path="$ctrl.local.dockerfilePath"
-          paths="$ctrl.local.dockerfileLocations.subdir"
+          paths="$ctrl.local.dockerfileLocations.dockerfile_paths"
           supports-full-listing="true"
-          is-valid-path="$ctrl.local.hasValidDockerfilePath"></dockerfile-path-select>
+          is-valid-path="$ctrl.local.hasValidDockerfilePath">
+        </dockerfile-path-select>
       </div>
 
       <div class="col-lg-8 col-md-8 col-sm-12 main-col"
@@ -268,10 +269,44 @@
       </div>
       <div class="col-lg-4 col-md-4 hidden-sm hidden-xs help-col">
         <p>Please select the location containing the Dockerfile to be built.</p>
-        <p>The build context will start at the location selected.</p>
       </div>
     </linear-workflow-section><!-- /Section: Dockerfile Location -->
 
+            <!-- Section: Context Location -->
+    <linear-workflow-section class="row"
+          section-id="contextlocation"
+          section-title="Select Docker Context"
+          section-valid="$ctrl.local.hasValidContextLocation">
+          <div class="col-lg-7 col-md-7 col-sm-12 main-col"
+               ng-if="$ctrl.local.dockerfileLocations.status == 'error'">
+            <div class="co-alert co-alert-warning">
+              {{ $ctrl.local.dockerfileLocations.message }}
+            </div>
+          </div>
+
+      <div class="col-lg-7 col-md-7 col-sm-12 main-col" ng-if="$ctrl.local.dockerfileLocations.status == 'success'">
+        <h3>Select Context</h3>
+        <strong>
+          Please select the context for the docker build
+        </strong>
+
+        <context-path-select
+          current-context="$ctrl.local.dockerContext"
+          current-path="$ctrl.local.dockerfilePath"
+          contexts="$ctrl.local.contexts"
+          is-valid-context="$ctrl.local.hasValidContextLocation">
+        </context-path-select>
+      </div>
+
+      <div class="col-lg-8 col-md-8 col-sm-12 main-col"
+           ng-if="!$ctrl.local.dockerfileLocations">
+        <span class="cor-loader-inline"></span> Retrieving Dockerfile locations
+      </div>
+      <div class="col-lg-4 col-md-4 hidden-sm hidden-xs help-col">
+        <p>Please select a docker context.</p>
+      </div>
+    </linear-workflow-section><!-- /Section: Context Location -->
+
     <!-- Section: Robot Account -->
     <linear-workflow-section class="row"
       section-id="verification"
diff --git a/static/js/directives/ui/manage-trigger-githost/manage-trigger-githost.component.ts b/static/js/directives/ui/manage-trigger-githost/manage-trigger-githost.component.ts
index 1af095941..6e49f2eb9 100644
--- a/static/js/directives/ui/manage-trigger-githost/manage-trigger-githost.component.ts
+++ b/static/js/directives/ui/manage-trigger-githost/manage-trigger-githost.component.ts
@@ -80,7 +80,14 @@ export class ManageTriggerGithostComponent implements ng.IComponentController {
 
     this.$scope.$watch(() => this.local.dockerfilePath, (path) => {
       if (path && this.local.selectedRepository) {
-        this.checkDockerfilePath(this.local.selectedRepository, path);
+        this.setPossibleContexts(path);
+        this.checkDockerfilePath(this.local.selectedRepository, path, this.local.dockerContext);
+      }
+    });
+
+    this.$scope.$watch(() => this.local.dockerContext, (context) => {
+      if (context && this.local.selectedRepository) {
+        this.checkDockerfilePath(this.local.selectedRepository, this.local.dockerfilePath, context);
       }
     });
 
@@ -117,7 +124,8 @@ export class ManageTriggerGithostComponent implements ng.IComponentController {
   public createTrigger(): void {
     var config: any = {
       build_source: this.local.selectedRepository.full_name,
-      subdir: this.local.dockerfilePath.substr(1) // Remove starting /
+      dockerfile_path: this.local.dockerfilePath,
+      context: this.local.dockerContext
     };
 
     if (this.local.triggerOptions.hasBranchTagFilter &&
@@ -271,6 +279,7 @@ export class ManageTriggerGithostComponent implements ng.IComponentController {
 
   private loadDockerfileLocations(repository: any): void {
     this.local.dockerfilePath = null;
+    this.local.dockerContext = null;
 
     var params = {
       'repository': this.repository.namespace + '/' + this.repository.name,
@@ -301,7 +310,7 @@ export class ManageTriggerGithostComponent implements ng.IComponentController {
       []);
   }
 
-  private checkDockerfilePath(repository: any, path: string): void {
+  private checkDockerfilePath(repository: any, path: string, context: string): void {
     this.local.triggerAnalysis = null;
     this.local.robotAccount = null;
 
@@ -312,7 +321,8 @@ export class ManageTriggerGithostComponent implements ng.IComponentController {
 
     var config = {
       'build_source': repository.full_name,
-      'subdir': path.substr(1)
+      'dockerfile_path': path.substr(1),
+      'context': context
     };
 
     var data = {
@@ -325,6 +335,12 @@ export class ManageTriggerGithostComponent implements ng.IComponentController {
         this.buildOrderedRobotAccounts();
       }, this.ApiService.errorDisplay('Could not analyze trigger'));
   }
+
+  private setPossibleContexts(path){
+    if(this.local.dockerfileLocations.contextMap){
+      this.local.contexts = this.local.dockerfileLocations.contextMap[path] || [];
+    }
+  }
 }
 
 
diff --git a/static/js/quay.module.ts b/static/js/quay.module.ts
index e1162bb32..980c5e9c2 100644
--- a/static/js/quay.module.ts
+++ b/static/js/quay.module.ts
@@ -7,6 +7,7 @@ import { RegexMatchViewComponent } from "./directives/ui/regex-match-view/regex-
 import { NgModule } from "angular-ts-decorators";
 import { QuayRoutes } from "./quay-routes.module";
 import { DockerfilePathSelectComponent } from './directives/ui/dockerfile-path-select/dockerfile-path-select.component';
+import { ContextPathSelectComponent } from './directives/ui/context-path-select/context-path-select.component';
 import { ManageTriggerCustomGitComponent } from './directives/ui/manage-trigger-custom-git/manage-trigger-custom-git.component';
 import { ManageTriggerGithostComponent } from './directives/ui/manage-trigger-githost/manage-trigger-githost.component';
 import { LinearWorkflowComponent } from './directives/ui/linear-workflow/linear-workflow.component';
@@ -31,6 +32,7 @@ import { DataFileServiceImpl } from './services/datafile/datafile.service.impl';
   declarations: [
     RegexMatchViewComponent,
     DockerfilePathSelectComponent,
+    ContextPathSelectComponent,
     ManageTriggerCustomGitComponent,
     ManageTriggerGithostComponent,
     LinearWorkflowComponent,
diff --git a/test/data/test.db b/test/data/test.db
index 874875be8..fc8c7f127 100644
Binary files a/test/data/test.db and b/test/data/test.db differ
diff --git a/test/test_api_usage.py b/test/test_api_usage.py
index 020a4faf9..2f2548df5 100644
--- a/test/test_api_usage.py
+++ b/test/test_api_usage.py
@@ -3852,6 +3852,7 @@ class FakeBuildTrigger(BuildTriggerHandler):
     prepared.subdirectory = 'subdir'
     prepared.metadata = {'foo': 'bar'}
     prepared.is_manual = True
+    prepared.context = '/'
     return prepared
 
   def get_repository_url(self):
@@ -4046,7 +4047,11 @@ class TestBuildTriggers(ApiTestCase):
                                                     trigger_uuid=trigger.uuid),
                                         data={'somevalue': 'meh'})
 
-    self.assertEquals({'status': 'success', 'subdir': ['/sometoken', '/foo', '/bar', '/meh']},
+    self.assertEquals({'status': 'success', 'dockerfile_paths': ['/sometoken', '/foo', '/bar', '/meh'],
+                       'contextMap': {'/bar': ['/'],
+                                      '/foo': ['/'],
+                                      '/meh': ['/'],
+                                      '/sometoken': ['/']}},
                       subdir_json)
 
     # Activate the trigger.
diff --git a/tools/migratebranchregex.py b/tools/migratebranchregex.py
index 832cf2bf2..791d2b477 100644
--- a/tools/migratebranchregex.py
+++ b/tools/migratebranchregex.py
@@ -5,6 +5,7 @@ import json
 from app import app
 from data import model
 from data.database import RepositoryBuildTrigger, configure
+from data.model.build import update_build_trigger
 
 configure(app.config)
 
@@ -40,8 +41,7 @@ def run_branchregex_migration():
       config['branchtag_regex'] = new_regex
 
       logger.debug("Updating to branchtag regex '%s'", new_regex)
-      trigger.config = json.dumps(config)
-      trigger.save()
+      update_build_trigger(trigger, config)
 
 if __name__ == "__main__":
   logging.basicConfig(level=logging.DEBUG)