diff --git a/tools/gate/devel/start.sh b/tools/gate/devel/start.sh
index ad18ad5d6..8c43487ab 100755
--- a/tools/gate/devel/start.sh
+++ b/tools/gate/devel/start.sh
@@ -55,8 +55,12 @@ function ansible_install {
   sudo -H -E pip install --no-cache-dir --upgrade pip
   sudo -H -E pip install --no-cache-dir --upgrade setuptools
   sudo -H -E pip install --no-cache-dir --upgrade pyopenssl
-  sudo -H -E pip install --no-cache-dir \
-    ansible \
+  # NOTE(srwilkers): Pinning ansible to 2.5.5, as pip installs 2.6 by default.
+  # 2.6 introduces a new command flag (init) for the docker_container module
+  # that is incompatible with what we have currently. 2.5.5 ensures we match
+  # what's deployed in the gates
+  sudo -H -E pip install --no-cache-dir --upgrade "ansible==2.5.5"
+  sudo -H -E pip install --no-cache-dir --upgrade \
     ara \
     yq
 }
diff --git a/tools/images/kubeadm-aio/Dockerfile b/tools/images/kubeadm-aio/Dockerfile
index 8f2caefe9..5f461cc8c 100644
--- a/tools/images/kubeadm-aio/Dockerfile
+++ b/tools/images/kubeadm-aio/Dockerfile
@@ -58,7 +58,12 @@ RUN set -ex ;\
     hash -r ;\
     pip --no-cache-dir install setuptools ;\
     pip --no-cache-dir install kubernetes ;\
-    pip --no-cache-dir install ansible ;\
+
+    # NOTE(srwilkers): Pinning ansible to 2.5.5, as pip installs 2.6 by default.
+    # 2.6 introduces a new command flag (init) for the docker_container module
+    # that is incompatible with what we have currently. 2.5.5 ensures we match
+    # what's deployed in the gates
+    pip --no-cache-dir install "ansible==2.5.5" ;\
     for BINARY in kubectl kubeadm; do \
       curl -sSL -o /usr/bin/${BINARY} \
         https://storage.googleapis.com/kubernetes-release/release/${KUBE_VERSION}/bin/linux/amd64/${BINARY} ;\