diff --git a/requirements.in b/requirements.in
index 8aa51ebb..71ede8cb 100644
--- a/requirements.in
+++ b/requirements.in
@@ -4,7 +4,7 @@ werkzeug >= 0.11.4
 # JPEG-compressed TIFFs.
 #
 # See https://github.com/loris-imageserver/loris/issues/405
-pillow >= 2.4.0, <5.0
+pillow >= 2.4.0, < 7.0
 
 configobj >= 4.7.2,<=5.0.0
 requests >= 2.12.0
diff --git a/requirements.txt b/requirements.txt
index f3e0eae4..1b19a308 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -13,8 +13,7 @@ configobj==5.0.0
 cryptography==2.3
 idna==2.6                 # via cryptography, requests
 netaddr==0.7.19
-olefile==0.45.1           # via pillow
-pillow==4.3.0
+pillow==6.2.0
 pycparser==2.18           # via cffi
 pyjwt==1.5.3
 requests==2.20.0
diff --git a/requirements_test.txt b/requirements_test.txt
index 2004558f..3f1d9cd3 100644
--- a/requirements_test.txt
+++ b/requirements_test.txt
@@ -18,9 +18,8 @@ idna==2.6
 mccabe==0.6.1             # via flake8
 mock==2.0.0               # via responses
 netaddr==0.7.19
-olefile==0.45.1
 pbr==3.1.1                # via mock
-pillow==4.3.0
+pillow==6.2.0
 py==1.5.2                 # via pytest
 pycodestyle==2.3.1        # via flake8
 pycparser==2.18