diff --git a/requirements/constraints.txt b/requirements/constraints.txt
index 62ea41cdcf..61532eea01 100644
--- a/requirements/constraints.txt
+++ b/requirements/constraints.txt
@@ -14,11 +14,6 @@ futures ; python_version == "2.7"
 python-openid ; python_version == "2.7"
 pysqlite ; python_version == "2.7"
 
-# pip-tools 3.9.0 has a few problems:
-#   https://github.com/jazzband/pip-tools/issues/851
-#   https://github.com/jazzband/pip-tools/issues/852
-pip-tools==3.8.0
-
 # Convert text markup to HTML; used in capa problems, forums, and course wikis; pin Markdown version as tests failed for its upgrade to latest release
 Markdown==2.6.11
 
diff --git a/requirements/edx/base.txt b/requirements/edx/base.txt
index 7fa283432d..750489e21c 100644
--- a/requirements/edx/base.txt
+++ b/requirements/edx/base.txt
@@ -208,7 +208,7 @@ pyuca==1.1
 pyyaml==5.1.2
 git+https://github.com/edx/RecommenderXBlock.git@1.4.1#egg=recommender-xblock==1.4.1
 redis==2.10.6
-reportlab==3.5.23
+reportlab==3.5.26
 requests-oauthlib==1.1.0
 requests==2.22.0
 rest-condition==1.0.3
diff --git a/requirements/edx/development.txt b/requirements/edx/development.txt
index a2c30b2ebd..9755955774 100644
--- a/requirements/edx/development.txt
+++ b/requirements/edx/development.txt
@@ -230,7 +230,7 @@ pbr==5.4.3
 pdfminer.six==20181108
 piexif==1.0.2
 pillow==6.1.0
-pip-tools==3.8.0
+pip-tools==4.1.0
 pkgconfig==1.5.1
 pluggy==0.13.0
 polib==1.1.0
@@ -281,7 +281,7 @@ pyyaml==5.1.2
 radon==3.0.3
 git+https://github.com/edx/RecommenderXBlock.git@1.4.1#egg=recommender-xblock==1.4.1
 redis==2.10.6
-reportlab==3.5.23
+reportlab==3.5.26
 requests-oauthlib==1.1.0
 requests==2.22.0
 rest-condition==1.0.3
diff --git a/requirements/edx/pip-tools.txt b/requirements/edx/pip-tools.txt
index b3854ee7e0..0e202ae09f 100644
--- a/requirements/edx/pip-tools.txt
+++ b/requirements/edx/pip-tools.txt
@@ -5,5 +5,5 @@
 #    make upgrade
 #
 click==7.0                # via pip-tools
-pip-tools==3.8.0
+pip-tools==4.1.0
 six==1.12.0
diff --git a/requirements/edx/testing.txt b/requirements/edx/testing.txt
index 3fb4219441..71186c536e 100644
--- a/requirements/edx/testing.txt
+++ b/requirements/edx/testing.txt
@@ -273,7 +273,7 @@ pyyaml==5.1.2
 radon==3.0.3
 git+https://github.com/edx/RecommenderXBlock.git@1.4.1#egg=recommender-xblock==1.4.1
 redis==2.10.6
-reportlab==3.5.23
+reportlab==3.5.26
 requests-oauthlib==1.1.0
 requests==2.22.0
 rest-condition==1.0.3