diff --git a/Jenkinsfile b/Jenkinsfile
index d1ea0baf153b..cc53da332e99 100644
--- a/Jenkinsfile
+++ b/Jenkinsfile
@@ -58,6 +58,11 @@ def configs = [
         imageName: 'pyca/cryptography-runner-jessie-libressl:2.4.5',
         toxenvs: ['py27'],
     ],
+    [
+        label: 'docker',
+        imageName: 'pyca/cryptography-runner-jessie-libressl:2.6.0',
+        toxenvs: ['py27'],
+    ],
     [
         label: 'docker',
         imageName: 'pyca/cryptography-runner-ubuntu-xenial',