diff --git a/deckhand/tests/integration/gabbits/document-crud-secret.yaml b/deckhand/tests/integration/gabbits/document-crud-secret.yaml
index cb4d5fe8..b32a782d 100644
--- a/deckhand/tests/integration/gabbits/document-crud-secret.yaml
+++ b/deckhand/tests/integration/gabbits/document-crud-secret.yaml
@@ -65,8 +65,8 @@ tests:
     response_headers:
       content-type: /^application\/octet-stream|^application\/octet-stream;\ charset=UTF-8/
     response_strings:
-      # base64.b64encode(repr("not-a-real-password"))
-      - J25vdC1hLXJlYWwtcGFzc3dvcmQn
+      # base64.encode_as_text(repr("not-a-real-password"))
+      - !!binary SjI1dmRDMWhMWEpsWVd3dGNHRnpjM2R2Y21Rbg==
 
   - name: verify_revision_documents_returns_secret_ref
     desc: Verify that the documents for the created revision returns the secret ref.
diff --git a/deckhand/tests/integration/gabbits/revision-delete-all-secrets.yaml b/deckhand/tests/integration/gabbits/revision-delete-all-secrets.yaml
index 15e2553a..e14fab4e 100644
--- a/deckhand/tests/integration/gabbits/revision-delete-all-secrets.yaml
+++ b/deckhand/tests/integration/gabbits/revision-delete-all-secrets.yaml
@@ -62,8 +62,8 @@ tests:
     response_headers:
       content-type: /^application\/octet-stream$|^application\/octet-stream;\ charset=UTF-8$/
     response_strings:
-      # base64.b64encode(repr("not-a-real-password"))
-      - J25vdC1hLXJlYWwtcGFzc3dvcmQn
+      # base64.encode_as_text(repr("not-a-real-password"))
+      - !!binary SjI1dmRDMWhMWEpsWVd3dGNHRnpjM2R2Y21Rbg==
 
   - name: delete_all_revisions
     desc: Delete all revisions from Deckhand, which should delete all secrets.
diff --git a/test-requirements.txt b/test-requirements.txt
index 9eda110f..600380e1 100644
--- a/test-requirements.txt
+++ b/test-requirements.txt
@@ -15,4 +15,5 @@ bandit==1.5.1
 gabbi==1.35.1
 pifpaf==2.1.2
 oslotest==3.7.0
-yq>=2.7.2
\ No newline at end of file
+yq>=2.7.2
+tox
diff --git a/tools/gate/playbooks/airskiff-deploy.yaml b/tools/gate/playbooks/airskiff-deploy.yaml
index 31406382..14f2a0d5 100644
--- a/tools/gate/playbooks/airskiff-deploy.yaml
+++ b/tools/gate/playbooks/airskiff-deploy.yaml
@@ -22,7 +22,16 @@
         daemon_reload: yes
         name: systemd-resolved
       become: yes
-
+    - name: ensure pip is installed
+      apt:
+        name: "{{ item }}"
+      with_items:
+        - python-pip
+        - python3-pip
+        - python-setuptools
+        - python3-setuptools
+      when: ansible_os_family == 'Debian'
+      become: true
     - name: Clone Required Repositories
       shell: |
         export CLONE_DECKHAND={{ CLONE_DECKHAND }}
diff --git a/tools/gate/playbooks/docker-image-build.yaml b/tools/gate/playbooks/docker-image-build.yaml
index 3af05b57..3685c541 100644
--- a/tools/gate/playbooks/docker-image-build.yaml
+++ b/tools/gate/playbooks/docker-image-build.yaml
@@ -47,10 +47,14 @@
           with_items:
             - docker.io
             - python-pip
+            - python3-pip
+            - python-setuptools
+            - python3-setuptools
           when: ansible_os_family == 'Debian'
         - pip:
             name: docker
             version: 2.7.0
+            executable: pip
       become: True
 
     - name: Make images
diff --git a/tools/gate/playbooks/osh-infra-deploy-docker.yaml b/tools/gate/playbooks/osh-infra-deploy-docker.yaml
index 7bf66fa2..11638281 100644
--- a/tools/gate/playbooks/osh-infra-deploy-docker.yaml
+++ b/tools/gate/playbooks/osh-infra-deploy-docker.yaml
@@ -33,11 +33,13 @@
   become: yes
   roles:
     - setup-firewall
+    - install-test-requirements
     - deploy-python-pip
     - deploy-docker
     - deploy-jq
   tags:
     - setup-firewall
+    - install-test-requirements
     - deploy-python-pip
     - deploy-docker
     - deploy-jq
diff --git a/tools/gate/playbooks/run-functional-tests-uwsgi.yaml b/tools/gate/playbooks/run-functional-tests-uwsgi.yaml
index e28d03e3..434aadfe 100644
--- a/tools/gate/playbooks/run-functional-tests-uwsgi.yaml
+++ b/tools/gate/playbooks/run-functional-tests-uwsgi.yaml
@@ -17,6 +17,7 @@
   roles:
     - disable-systemd-resolved
     - install-postgresql
+    - install-test-requirements
     - run-functional-tests
   tags:
     - install-postgresql
diff --git a/tools/gate/playbooks/run-integration-tests-uwsgi.yaml b/tools/gate/playbooks/run-integration-tests-uwsgi.yaml
index 10bc32be..b5f1e3f1 100644
--- a/tools/gate/playbooks/run-integration-tests-uwsgi.yaml
+++ b/tools/gate/playbooks/run-integration-tests-uwsgi.yaml
@@ -17,6 +17,7 @@
   roles:
     - disable-systemd-resolved
     - install-postgresql
+    - install-test-requirements
     - run-integration-tests
   tags:
     - install-postgresql
diff --git a/tools/gate/roles/install-test-requirements/tasks/install-test-requirements.yaml b/tools/gate/roles/install-test-requirements/tasks/install-test-requirements.yaml
index 44583c03..1f38fe95 100644
--- a/tools/gate/roles/install-test-requirements/tasks/install-test-requirements.yaml
+++ b/tools/gate/roles/install-test-requirements/tasks/install-test-requirements.yaml
@@ -20,7 +20,8 @@
 - name: Install pip3 and gabbi
   shell: |
     set -xe;
-    apt-get install -y python-pip
+    apt-get install -y python-pip python3-pip \
+      python-setuptools python3-setuptools
     pip install --upgrade pip
     pip install -r test-requirements.txt
   args: