diff --git a/requirements/edx/base.txt b/requirements/edx/base.txt
index a67b8cf0f2..eddde18673 100644
--- a/requirements/edx/base.txt
+++ b/requirements/edx/base.txt
@@ -111,8 +111,8 @@ edx-django-oauth2-provider==1.3.5
 edx-django-release-util==0.3.1
 edx-django-sites-extensions==2.3.1
 edx-django-utils==1.0.3
-edx-drf-extensions==2.2.0
-edx-enterprise==1.4.9
+edx-drf-extensions==2.2.1
+edx-enterprise==1.4.10
 edx-i18n-tools==0.4.8
 edx-milestones==0.1.13
 edx-oauth2-provider==1.2.2
diff --git a/requirements/edx/development.txt b/requirements/edx/development.txt
index 4cdbec14c5..4419d6b2fa 100644
--- a/requirements/edx/development.txt
+++ b/requirements/edx/development.txt
@@ -72,7 +72,6 @@ code-annotations==0.3.1
 colorama==0.4.1
 configparser==3.7.4
 constantly==15.1.0
-contextlib2==0.5.5
 coreapi==2.3.3
 coreschema==0.0.4
 coverage==4.4
@@ -133,8 +132,8 @@ edx-django-oauth2-provider==1.3.5
 edx-django-release-util==0.3.1
 edx-django-sites-extensions==2.3.1
 edx-django-utils==1.0.3
-edx-drf-extensions==2.2.0
-edx-enterprise==1.4.9
+edx-drf-extensions==2.2.1
+edx-enterprise==1.4.10
 edx-i18n-tools==0.4.8
 edx-lint==1.1.2
 edx-milestones==0.1.13
@@ -181,7 +180,6 @@ httpretty==0.9.6
 hyperlink==19.0.0
 idna==2.8
 imagesize==1.1.0          # via sphinx
-importlib-metadata==0.9
 incremental==17.5.0
 inflect==2.1.0
 ipaddress==1.0.22
@@ -194,7 +192,7 @@ jmespath==0.9.4
 jsondiff==1.1.1
 jsonfield==2.0.2
 kombu==3.0.37
-lazy-object-proxy==1.3.1
+lazy-object-proxy==1.4.0
 lazy==1.1
 lepl==5.1.3
 libsass==0.10.0
@@ -235,7 +233,7 @@ pdfminer.six==20181108
 piexif==1.0.2
 pillow==6.0.0
 pip-tools==3.6.1
-pluggy==0.10.0
+pluggy==0.11.0
 polib==1.1.0
 psutil==1.2.1
 py2neo==3.1.2
@@ -348,5 +346,4 @@ xblock-utils==1.2.1
 xblock==1.2.2
 xmltodict==0.12.0
 zendesk==1.1.1
-zipp==0.4.0
 zope.interface==4.6.0
diff --git a/requirements/edx/testing.txt b/requirements/edx/testing.txt
index be1cd4aba5..e96f69bb50 100644
--- a/requirements/edx/testing.txt
+++ b/requirements/edx/testing.txt
@@ -68,9 +68,8 @@ click-log==0.3.2          # via edx-lint
 click==7.0
 code-annotations==0.3.1
 colorama==0.4.1           # via radon
-configparser==3.7.4       # via entrypoints, flake8, importlib-metadata, pylint
+configparser==3.7.4       # via entrypoints, flake8, pylint
 constantly==15.1.0        # via twisted
-contextlib2==0.5.5        # via importlib-metadata
 coreapi==2.3.3
 coreschema==0.0.4
 coverage==4.4
@@ -129,8 +128,8 @@ edx-django-oauth2-provider==1.3.5
 edx-django-release-util==0.3.1
 edx-django-sites-extensions==2.3.1
 edx-django-utils==1.0.3
-edx-drf-extensions==2.2.0
-edx-enterprise==1.4.9
+edx-drf-extensions==2.2.1
+edx-enterprise==1.4.10
 edx-i18n-tools==0.4.8
 edx-lint==1.1.2
 edx-milestones==0.1.13
@@ -175,7 +174,6 @@ httplib2==0.12.3
 httpretty==0.9.6
 hyperlink==19.0.0         # via twisted
 idna==2.8
-importlib-metadata==0.9   # via pluggy
 incremental==17.5.0       # via twisted
 inflect==2.1.0
 ipaddress==1.0.22
@@ -188,7 +186,7 @@ jmespath==0.9.4
 jsondiff==1.1.1
 jsonfield==2.0.2
 kombu==3.0.37
-lazy-object-proxy==1.3.1  # via astroid
+lazy-object-proxy==1.4.0  # via astroid
 lazy==1.1
 lepl==5.1.3
 libsass==0.10.0
@@ -220,14 +218,14 @@ pa11ycrawler==1.7.3
 packaging==19.0           # via caniusepython3
 parsel==1.5.1             # via scrapy
 path.py==8.2.1
-pathlib2==2.3.3           # via importlib-metadata, pytest, pytest-django
+pathlib2==2.3.3           # via pytest, pytest-django
 pathtools==0.1.2
 paver==1.3.4
 pbr==5.2.0
 pdfminer.six==20181108
 piexif==1.0.2
 pillow==6.0.0
-pluggy==0.10.0            # via pytest, tox
+pluggy==0.11.0            # via pytest, tox
 polib==1.1.0
 psutil==1.2.1
 py2neo==3.1.2
@@ -334,5 +332,4 @@ xblock-utils==1.2.1
 xblock==1.2.2
 xmltodict==0.12.0         # via moto
 zendesk==1.1.1
-zipp==0.4.0               # via importlib-metadata
 zope.interface==4.6.0     # via twisted