diff --git a/runners/debian/Dockerfile b/runners/debian/Dockerfile
index 9227839a..69574eed 100644
--- a/runners/debian/Dockerfile
+++ b/runners/debian/Dockerfile
@@ -17,11 +17,11 @@ RUN apt-get -qq update && apt-get install -qq -y \
     curl
 
 # Remove when we drop 2.7 support from pyOpenSSL
-RUN apt-get -qq update; if grep -q "stretch" /etc/debian_version; then apt-get install -qq -y python-dev; fi
-RUN apt-get -qq update; if grep -q "sid" /etc/debian_version; then apt-get install -qq -y python3-distutils; fi
+RUN apt-get -qq update; if grep -q "stretch" /etc/os-release; then apt-get install -qq -y python-dev; fi
+RUN apt-get -qq update; if grep -q "sid" /etc/os-release; then apt-get install -qq -y python3-distutils; fi
 
 # Remove /3.5/ when we drop stretch!
-RUN curl -sSL https://bootstrap.pypa.io/3.5/get-pip.py | python3
+RUN curl -sSL https://bootstrap.pypa.io/pip/3.5/get-pip.py | python3
 
 RUN pip install tox coverage