diff --git a/requirements/constraints.txt b/requirements/constraints.txt
index 36a494baa8..105781d280 100644
--- a/requirements/constraints.txt
+++ b/requirements/constraints.txt
@@ -15,6 +15,9 @@ six==1.11.0
 # 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
 
+# 5.4.0 causes cms/djangoapps/api/v1/tests/test_views/test_course_runs.py::CourseRunViewSetTests::test_images_upload to fail
+pillow==5.3.0
+
 # required by edx-lint and pinned explicitly here because newer versions don't guarantee python 2 support.
 # Can be removed when we get to Python 3.
 pylint-plugin-utils==0.3
diff --git a/requirements/edx/base.in b/requirements/edx/base.in
index 05b6918886..1fe9b35b0c 100644
--- a/requirements/edx/base.in
+++ b/requirements/edx/base.in
@@ -132,7 +132,7 @@ rest-condition                      # DRF's recommendation for supporting comple
 rfc6266-parser                      # Used to generate Content-Disposition headers.
 social-auth-app-django<3.0.0
 social-auth-core<2.0.0
-pysrt==0.4.7                        # Support for SubRip subtitle files, used in the video XModule
+pysrt                               # Support for SubRip subtitle files, used in the video XModule
 pytz                                # Time zone information database
 PyYAML                              # Used to parse XModule resource templates
 redis==2.10.6                       # celery task broker
diff --git a/requirements/edx/base.txt b/requirements/edx/base.txt
index 0e1e1c9465..a7b49c7139 100644
--- a/requirements/edx/base.txt
+++ b/requirements/edx/base.txt
@@ -60,7 +60,6 @@ botocore==1.8.17
 celery==3.1.25
 certifi==2018.11.29
 cffi==1.11.5
-charade==1.0.3            # via pysrt
 chardet==3.0.4
 click==7.0                # via user-util
 coreapi==2.3.3            # via django-rest-swagger, openapi-codec
@@ -199,7 +198,7 @@ pyjwt==1.5.2
 pymongo==2.9.1
 pynliner==0.8.0
 pyparsing==2.2.0
-pysrt==0.4.7
+pysrt==1.1.1
 python-dateutil==2.4.0
 python-levenshtein==0.12.0
 python-memcached==1.48
diff --git a/requirements/edx/development.txt b/requirements/edx/development.txt
index db8de53ab5..972cb386d3 100644
--- a/requirements/edx/development.txt
+++ b/requirements/edx/development.txt
@@ -69,7 +69,6 @@ botocore==1.8.17
 celery==3.1.25
 certifi==2018.11.29
 cffi==1.11.5
-charade==1.0.3
 chardet==3.0.4
 click-log==0.1.8
 click==7.0
@@ -266,7 +265,7 @@ pyopenssl==18.0.0
 pyparsing==2.2.0
 pyquery==1.4.0
 pysqlite==2.8.3
-pysrt==0.4.7
+pysrt==1.1.1
 pytest-attrib==0.1.3
 pytest-cov==2.5.1
 pytest-django==3.1.2
diff --git a/requirements/edx/testing.txt b/requirements/edx/testing.txt
index 04d0492bcb..68b11e23c4 100644
--- a/requirements/edx/testing.txt
+++ b/requirements/edx/testing.txt
@@ -66,7 +66,6 @@ botocore==1.8.17
 celery==3.1.25
 certifi==2018.11.29
 cffi==1.11.5
-charade==1.0.3
 chardet==3.0.4
 click-log==0.1.8          # via edx-lint
 click==7.0
@@ -255,7 +254,7 @@ pyopenssl==18.0.0         # via scrapy
 pyparsing==2.2.0
 pyquery==1.4.0
 pysqlite==2.8.3
-pysrt==0.4.7
+pysrt==1.1.1
 pytest-attrib==0.1.3
 pytest-cov==2.5.1
 pytest-django==3.1.2