diff --git a/tox.ini b/tox.ini
index 8b7176381..94cd305aa 100644
--- a/tox.ini
+++ b/tox.ini
@@ -78,6 +78,10 @@ setenv =
     PYTHONHASHSEED = 0
 
 [testenv:oldest]
+# Setting basepython allows the tests to fail fast if that version of Python
+# isn't available instead of potentially trying to use a newer version of
+# Python which is unlikely to work.
+basepython = python3.6
 commands =
     {[testenv]commands}
 setenv =
@@ -85,36 +89,48 @@ setenv =
     CERTBOT_OLDEST=1
 
 [testenv:acme-oldest]
+basepython =
+    {[testenv:oldest]basepython}
 commands =
     {[base]install_and_test} acme[dev]
 setenv =
     {[testenv:oldest]setenv}
 
 [testenv:apache-oldest]
+basepython =
+    {[testenv:oldest]basepython}
 commands =
     {[base]install_and_test} certbot-apache
 setenv =
     {[testenv:oldest]setenv}
 
 [testenv:apache-v2-oldest]
+basepython =
+    {[testenv:oldest]basepython}
 commands =
     {[base]install_and_test} certbot-apache[dev]
 setenv =
     {[testenv:oldest]setenv}
 
 [testenv:certbot-oldest]
+basepython =
+    {[testenv:oldest]basepython}
 commands =
     {[base]install_and_test} certbot[dev]
 setenv =
     {[testenv:oldest]setenv}
 
 [testenv:dns-oldest]
+basepython =
+    {[testenv:oldest]basepython}
 commands =
     {[base]install_and_test} {[base]dns_packages}
 setenv =
     {[testenv:oldest]setenv}
 
 [testenv:nginx-oldest]
+basepython =
+    {[testenv:oldest]basepython}
 commands =
     {[base]install_and_test} certbot-nginx
     python tests/lock_test.py
@@ -238,6 +254,8 @@ commands =
 passenv = DOCKER_*
 
 [testenv:integration-certbot-oldest]
+basepython =
+    {[testenv:oldest]basepython}
 commands =
     {[base]pip_install} certbot
     {[base]pip_install} certbot-ci
@@ -247,6 +265,8 @@ passenv = DOCKER_*
 setenv = {[testenv:oldest]setenv}
 
 [testenv:integration-nginx-oldest]
+basepython =
+    {[testenv:oldest]basepython}
 commands =
     {[base]pip_install} certbot-nginx
     {[base]pip_install} certbot-ci