diff --git a/requirements/constraints.txt b/requirements/constraints.txt
index e355b75261378a88648cbfaff0e2aba8ed9e2f4b..5ab4a83dd7fc4b3149ef1d495035e9d11811a78f 100644
--- a/requirements/constraints.txt
+++ b/requirements/constraints.txt
@@ -11,9 +11,6 @@
 # The CORS_ORIGIN_WHITELIST changes in a backwards incompatible way in 3.0.0, needs matching configuration repo changes
 django-cors-headers<3.0.0
 
-# Constraining this since the newer versions no longer work with the deprecated MIDDLEWARE_CLASSES setting
-django-debug-toolbar<2.0
-
 # Version 1.2.0 dropped support for Django 1.11
 django-oauth-toolkit<1.2.0
 
@@ -80,3 +77,6 @@ mock<4.0.0
 
 # django-storages version 1.9 drops support for boto storage backend.
 django-storages<1.9
+
+# Support was dropped for Python 3.5, Django 2.0, Django 2.1, DRF 3.7
+drf-yasg<1.17.1
diff --git a/requirements/edx/base.txt b/requirements/edx/base.txt
index 3195cdb19045b734bd85f8cf4c1182bcab88cf88..2256e042869e02216a17109a45b38586eecab148 100644
--- a/requirements/edx/base.txt
+++ b/requirements/edx/base.txt
@@ -91,7 +91,7 @@ djangorestframework-xml==1.4.0  # via edx-enterprise
 djangorestframework==3.9.4
 docopt==0.6.2
 docutils==0.16            # via botocore
-drf-yasg==1.17.1          # via edx-api-doc-tools
+drf-yasg==1.17.0          # via edx-api-doc-tools
 edx-ace==0.1.13
 edx-analytics-data-api-client==0.15.3
 edx-api-doc-tools==1.0.2
diff --git a/requirements/edx/development.txt b/requirements/edx/development.txt
index 393e8d2522f0be342e69b066ec7498c514ebeded..d391481ef5c3d06d77ddf1702c2c32455242906c 100644
--- a/requirements/edx/development.txt
+++ b/requirements/edx/development.txt
@@ -72,7 +72,7 @@ django-config-models==2.0.0
 django-cors-headers==2.5.3
 django-countries==5.5
 django-crum==0.7.5
-django-debug-toolbar==1.11
+django-debug-toolbar==2.2
 django-fernet-fields==0.6
 django-filter==2.2.0
 django-ipware==2.1.0
@@ -103,7 +103,7 @@ djangorestframework-xml==1.4.0
 djangorestframework==3.9.4
 docopt==0.6.2
 docutils==0.16
-drf-yasg==1.17.1
+drf-yasg==1.17.0
 edx-ace==0.1.13
 edx-analytics-data-api-client==0.15.3
 edx-api-doc-tools==1.0.2
@@ -289,7 +289,7 @@ social-auth-core==3.2.0
 git+https://github.com/jazzband/sorl-thumbnail.git@13bedfb7d2970809eda597e3ef79318a6fa80ac2#egg=sorl-thumbnail
 sortedcontainers==2.1.0
 soupsieve==1.9.5
-sphinx==2.4.1             # via edx-sphinx-theme, sphinxcontrib-httpdomain
+sphinx==2.4.2             # via edx-sphinx-theme, sphinxcontrib-httpdomain
 sphinxcontrib-applehelp==1.0.1  # via sphinx
 sphinxcontrib-devhelp==1.0.1  # via sphinx
 sphinxcontrib-htmlhelp==1.0.2  # via sphinx
diff --git a/requirements/edx/testing.txt b/requirements/edx/testing.txt
index 12567a823c7e077fcd128fe08a6e842fdc0b5b90..dfebc5f8cbc10a79e51d96de3ff2fc42285b3e63 100644
--- a/requirements/edx/testing.txt
+++ b/requirements/edx/testing.txt
@@ -99,7 +99,7 @@ djangorestframework-xml==1.4.0
 djangorestframework==3.9.4
 docopt==0.6.2
 docutils==0.16
-drf-yasg==1.17.1
+drf-yasg==1.17.0
 edx-ace==0.1.13
 edx-analytics-data-api-client==0.15.3
 edx-api-doc-tools==1.0.2