diff --git a/.gitignore b/.gitignore
index 0ff6c0f6..34420bd7 100644
--- a/.gitignore
+++ b/.gitignore
@@ -109,6 +109,9 @@ ENV/
 #pycharm-ide
 .idea/
 
+# osx
+.DS_Store
+
 # makefile build/lint artifacts
 /charts/deckhand/*.tgz
 /charts/deckhand/*.lock
diff --git a/.zuul.yaml b/.zuul.yaml
index aa250f2f..d5691ab5 100644
--- a/.zuul.yaml
+++ b/.zuul.yaml
@@ -16,10 +16,8 @@
         - airship-deckhand-linter
         - airship-deckhand-ubuntu:
             voting: false
-            irrelevant-files:
-              - ^.*\.rst$
-              - ^doc/.*$
-              - ^releasenotes/.*$
+        - airship-deckhand-tox-functional
+        - airship-deckhand-tox-functional-py35
     gate:
       jobs:
         - airship-deckhand-linter
@@ -29,19 +27,23 @@
         #       - ^.*\.rst$
         #       - ^doc/.*$
         #       - ^releasenotes/.*$
+        - airship-deckhand-tox-functional
+        - airship-deckhand-tox-functional-py35
 
 - job:
     name: airship-deckhand-linter
+    description: |
+      Lints all files by checking them for whitespace.
     run: tools/gate/playbooks/zuul-linter.yaml
     nodeset: openstack-helm-single-node
 
 - job:
-    name: airship-deckhand
+    name: airship-deckhand-base
     roles:
       - zuul: openstack/openstack-helm-infra
     vars:
       zuul_osh_infra_relative_path: ../openstack-helm-infra/
-    timeout: 7200
+    timeout: 3600
     pre-run:
       - tools/gate/playbooks/osh-infra-upgrade-host.yaml
       - tools/gate/playbooks/osh-infra-deploy-docker.yaml
@@ -54,5 +56,48 @@
 
 - job:
     name: airship-deckhand-ubuntu
-    parent: airship-deckhand
+    parent: airship-deckhand-base
     nodeset: openstack-helm-single-node
+    irrelevant-files:
+      - ^.*\.rst$
+      - ^doc/.*$
+      - ^releasenotes/.*$
+
+- job:
+    name: airship-deckhand-tox-functional-base
+    description: |
+      Base job for running airship-deckhand functional tests. Runs tests
+      against Docker image generated from source code.
+    roles:
+      - zuul: openstack/openstack-helm-infra
+    timeout: 3600
+    pre-run:
+      - tools/gate/playbooks/osh-infra-upgrade-host.yaml
+      - tools/gate/playbooks/osh-infra-deploy-docker.yaml
+    run: tools/gate/playbooks/run-functional-tests.yaml
+    required-projects:
+      - openstack/openstack-helm-infra
+    irrelevant-files:
+      - ^.*\.rst$
+      - ^doc/.*$
+      - ^releasenotes/.*$
+
+- job:
+    name: airship-deckhand-tox-functional
+    description: |
+      Run tox-based functional tests for the Airship Deckhand project under
+      cPython version 2.7. Uses tox with the ``functional`` environment.
+    parent: airship-deckhand-tox-functional-base
+    nodeset: openstack-helm-single-node
+    vars:
+      tox_envlist: functional
+
+- job:
+    name: airship-deckhand-tox-functional-py35
+    description: |
+      Run tox-based functional tests for the Airship Deckhand project under
+      cPython version 3.5. Uses tox with the ``functional-py35`` environment.
+    parent: airship-deckhand-tox-functional-base
+    nodeset: openstack-helm-single-node
+    vars:
+      tox_envlist: functional-py35
diff --git a/tools/common-tests.sh b/tools/common-tests.sh
index df766078..db0b1794 100644
--- a/tools/common-tests.sh
+++ b/tools/common-tests.sh
@@ -22,6 +22,7 @@ function deploy_postgre {
     #######################################
     set -xe
 
+    # TODO(felipemonteiro): Use OSH PostgreSQL chart.
     POSTGRES_ID=$(
         sudo docker run \
             --detach \
diff --git a/tools/functional-tests.sh b/tools/functional-tests.sh
index 772380c3..2daea3fd 100755
--- a/tools/functional-tests.sh
+++ b/tools/functional-tests.sh
@@ -33,11 +33,13 @@ function cleanup_deckhand {
 
     rm -rf $CONF_DIR
 
-    # Kill all processes and child processes (for example, if workers > 1)
-    # if using uwsgi only.
-    PGID=$(ps -o comm -o pgid | grep uwsgi | grep -o [0-9]* | head -n 1)
-    if [ -n "$PGID" ]; then
-        setsid kill -- -$PGID
+    if [ -z "$DECKHAND_IMAGE" ]; then
+        # Kill uwsgi service if it is still running.
+        PID=$( sudo netstat -tulpn | grep ":9000" | head -n 1 | awk '{print $NF}' )
+        if [ -n $PID ]; then
+            PID=${PID%/*}
+            sudo kill -9 $PID
+        fi
     fi
 }
 
diff --git a/tools/gate/playbooks/roles b/tools/gate/playbooks/roles
new file mode 120000
index 00000000..7b9ade87
--- /dev/null
+++ b/tools/gate/playbooks/roles
@@ -0,0 +1 @@
+../roles/
\ No newline at end of file
diff --git a/tools/gate/playbooks/run-functional-tests.yaml b/tools/gate/playbooks/run-functional-tests.yaml
new file mode 100644
index 00000000..b5a6dd4e
--- /dev/null
+++ b/tools/gate/playbooks/run-functional-tests.yaml
@@ -0,0 +1,28 @@
+# Copyright 2018 AT&T Intellectual Property.  All other rights reserved.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+- hosts: all
+  gather_facts: False
+  become: yes
+  roles:
+    - build-images
+  tags:
+    - build-images
+
+- hosts: all
+  gather_facts: False
+  roles:
+    - run-tests
+  tags:
+    - run-tests
diff --git a/tools/gate/roles/build-images/tasks/airship-deckhand.yaml b/tools/gate/roles/build-images/tasks/airship-deckhand.yaml
new file mode 100644
index 00000000..bf5623e7
--- /dev/null
+++ b/tools/gate/roles/build-images/tasks/airship-deckhand.yaml
@@ -0,0 +1,56 @@
+# Copyright 2018 AT&T Intellectual Property.  All other rights reserved.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+- name: set zuul_site_mirror_fqdn from env var if not defined
+  when: zuul_site_mirror_fqdn is not defined
+  set_fact:
+    zuul_site_mirror_fqdn: "{{ lookup('env','zuul_site_mirror_fqdn') }}"
+
+# NOTE(portdirect): Untill https://github.com/ansible/ansible/issues/21433 is
+# resolved, we build with a shell script to make use of the host network.
+- name: Build Airship-Deckhand Image
+  block:
+    # NOTE(portdirect): We do this to ensure we are feeding the docker build
+    # a clean path to work with.
+    - name: Airship-Deckhand image build path
+      shell: cd "{{ work_dir }}"; pwd
+      register: airship_deckhand_path
+      vars:
+        zuul_airship_deckhand_relative_path: ../airship-deckhand
+        work_dir: "{{ zuul.project.src_dir }}/{{ zuul_airship_deckhand_relative_path | default('') }}"
+
+    - name: Airship-Deckhand image build path
+      shell: |-
+              set -ex;
+              docker build \
+                --network host \
+                --force-rm \
+                --label zuul \
+                --file images/deckhand/Dockerfile \
+                {% if zuul_site_mirror_fqdn is defined and zuul_site_mirror_fqdn %}
+                --build-arg UBUNTU_URL="http://{{ zuul_site_mirror_fqdn }}/ubuntu/" \
+                --build-arg ALLOW_UNAUTHENTICATED="true" \
+                --build-arg PIP_INDEX_URL="http://{{ zuul_site_mirror_fqdn }}/pypi/simple" \
+                --build-arg PIP_TRUSTED_HOST="{{ zuul_site_mirror_fqdn }}" \
+                {% endif %}
+                .
+      args:
+        chdir: "{{ airship_deckhand_path.stdout }}"
+        executable: /bin/bash
+
+    - name: Register Deckhand Image ID
+      shell: |-
+              set -e;
+              echo $( docker images --filter label=zuul | awk '{print $3}' | head -2 | tail -1 )
+      register: deckhand_image_id
diff --git a/tools/gate/roles/build-images/tasks/main.yaml b/tools/gate/roles/build-images/tasks/main.yaml
new file mode 100644
index 00000000..8fd8a90f
--- /dev/null
+++ b/tools/gate/roles/build-images/tasks/main.yaml
@@ -0,0 +1,15 @@
+# Copyright 2018 AT&T Intellectual Property.  All other rights reserved.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+- include: airship-deckhand.yaml
diff --git a/tools/gate/roles/run-tests/tasks/main.yaml b/tools/gate/roles/run-tests/tasks/main.yaml
new file mode 100644
index 00000000..a1c8c122
--- /dev/null
+++ b/tools/gate/roles/run-tests/tasks/main.yaml
@@ -0,0 +1,15 @@
+# Copyright 2018 AT&T Intellectual Property.  All other rights reserved.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+- include: tox-tests.yaml
diff --git a/tools/gate/roles/run-tests/tasks/tox-tests.yaml b/tools/gate/roles/run-tests/tasks/tox-tests.yaml
new file mode 100644
index 00000000..a81ebb6e
--- /dev/null
+++ b/tools/gate/roles/run-tests/tasks/tox-tests.yaml
@@ -0,0 +1,22 @@
+# Copyright 2018 AT&T Intellectual Property.  All other rights reserved.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+- name: Run Tox Tests
+  shell: |
+    set -xe;
+    tox -e {{ tox_envlist }}
+  args:
+    chdir: "{{ zuul.project.src_dir }}"
+  environment:
+    DECKHAND_IMAGE: "{{ deckhand_image_id.stdout }}"
diff --git a/tox.ini b/tox.ini
index 28f53eac..b25a6309 100644
--- a/tox.ini
+++ b/tox.ini
@@ -1,5 +1,5 @@
 [tox]
-envlist = py{35,27},py{35,27}-{postgresql},cover,pep8,bandit,docs
+envlist = py{35,27},py{35,27}-{postgresql},functional,cover,pep8,bandit,docs
 
 [testenv]
 usedevelop = True
@@ -41,7 +41,17 @@ commands =
     {toxinidir}/tools/run_pifpaf.sh '{posargs}'
 
 [testenv:functional]
-# Always run functional tests using Python 3.
+basepython = python2.7
+setenv = VIRTUAL_ENV={envdir}
+         OS_TEST_PATH=./deckhand/tests/functional
+         LANGUAGE=en_US
+deps = -r{toxinidir}/requirements.txt
+       -r{toxinidir}/test-requirements.txt
+commands =
+  find . -type f -name "*.pyc" -delete
+  {toxinidir}/tools/functional-tests.sh '{posargs}'
+
+[testenv:functional-py35]
 basepython=python3.5
 setenv = VIRTUAL_ENV={envdir}
          OS_TEST_PATH=./deckhand/tests/functional