diff --git a/images/airflow/Dockerfile.ubuntu_xenial b/images/airflow/Dockerfile.ubuntu_xenial
index 1333768f..ca32fdf0 100644
--- a/images/airflow/Dockerfile.ubuntu_xenial
+++ b/images/airflow/Dockerfile.ubuntu_xenial
@@ -72,6 +72,7 @@ RUN set -ex && \
     python3-pip \
     python3-dev \
     python3-dateutil \
+    python3-openssl \
     make \
     --no-install-recommends \
     && python3 -m pip install -U 'pip<21.0' \
@@ -111,7 +112,8 @@ RUN useradd -ms /bin/bash -d ${AIRFLOW_HOME} airflow \
 #    https://github.com/puckel/docker-airflow/issues/77
 # Install Airflow directly to allow overriding source
 COPY images/airflow/requirements.txt /tmp/
-RUN pip3 install -r /tmp/requirements.txt --no-cache-dir \
+RUN sed -i "s/pyOpenSSL==.*//" /tmp/requirements.txt \
+    && pip3 install -r /tmp/requirements.txt --no-cache-dir \
     && pip3 install $AIRFLOW_SRC --no-cache-dir \
     && (pip3 uninstall -y snakebite || true) \
     && (pip3 uninstall -y psycopg2 || true) \
diff --git a/images/shipyard/Dockerfile.ubuntu_xenial b/images/shipyard/Dockerfile.ubuntu_xenial
index 0ff2e621..e0c0be23 100644
--- a/images/shipyard/Dockerfile.ubuntu_xenial
+++ b/images/shipyard/Dockerfile.ubuntu_xenial
@@ -99,12 +99,15 @@ COPY ${ctx_base}/shipyard_airflow /home/shipyard/shipyard/
       python3-pip \
     ' \
     && apt-get -qq update \
-    && apt-get -y install -y $buildDeps --no-install-recommends \
+    && apt-get -y install -y \
+        $buildDeps \
+        python3-openssl \
+        libffi-dev \
+        python3-dev \
+            --no-install-recommends \
     && python3 -m pip install -U 'pip<21.0' \
     && python3 -m pip install -U setuptools \
-    && pip3 install -r /home/shipyard/client_requirements.txt --no-cache-dir \
-    && cd /home/shipyard/shipyard_client \
-    && python3 setup.py install \
+    && sed -i "s/pyOpenSSL==.*//" /home/shipyard/client_requirements.txt\
     && pip3 install -r /home/shipyard/api_requirements.txt --no-cache-dir \
     && cd /home/shipyard/shipyard \
     && python3 setup.py install \