diff --git a/test/runner/requirements/constraints.txt b/test/runner/requirements/constraints.txt
index 1803ac5c18..df561d4253 100644
--- a/test/runner/requirements/constraints.txt
+++ b/test/runner/requirements/constraints.txt
@@ -11,7 +11,7 @@ ncclient >= 0.5.2 # Need features added in 0.5.2 and greater
 idna < 2.6 # requests requires idna < 2.6, but cryptography will cause the latest version to be installed instead
 paramiko < 2.4.0 ; python_version < '2.7' # paramiko 2.4.0 drops support for python 2.6
 pytest < 3.3.0 ; python_version < '2.7' # pytest 3.3.0 drops support for python 2.6
-pytest < 3.10.0 ; python_version >= '2.7' # pytest 3.10.0+ causes some tests to crash
+pytest < 5.0.0 ; python_version == '2.7' # pytest 5.0.0 and later will no longer support python 2.7
 pytest-forked < 1.0.2 ; python_version < '2.7' # pytest-forked 1.0.2 and later require python 2.7 or later
 pytest-forked >= 1.0.2 ; python_version >= '2.7' # pytest-forked before 1.0.2 does not work with pytest 4.2.0+ (which requires python 2.7+)
 ntlm-auth >= 1.0.6 # message encryption support