diff --git a/Makefile b/Makefile
index 2a730c1..4cc1507 100644
--- a/Makefile
+++ b/Makefile
@@ -14,8 +14,8 @@ init:
 	git submodule init && git submodule update
 
 setup-venv:
-	if [ -f $(VENV) ]; then virtualenv $(VENV); fi;
-	$(IN_VENV) pip install -r requirements.txt && pip install -r dev-requirements.txt
+	if [ ! -f $(VENV) ]; then virtualenv $(VENV); fi;
+	$(IN_VENV) pip install -r requirements.txt
 
 packer:
 	$(IN_VENV) python yaml-to-json.py --force packer.yaml
diff --git a/packer.json b/packer.json
index 03dee8a..c07588b 100644
--- a/packer.json
+++ b/packer.json
@@ -30,7 +30,7 @@
   "builders": [
     {
       "guest_additions_path": "VBoxGuestAdditions_{{.Version}}.iso", 
-      "iso_url": "http://releases.ubuntu.com/16.04/ubuntu-16.04.3-server-amd64.iso", 
+      "iso_url": "http://releases.ubuntu.com/16.04/ubuntu-16.04.4-server-amd64.iso", 
       "ssh_port": 22, 
       "ssh_username": "{{ user `username` }}", 
       "iso_checksum_type": "sha256", 
@@ -83,7 +83,7 @@
       ], 
       "guest_os_type": "Ubuntu_64", 
       "name": "virtualbox-iso", 
-      "iso_checksum": "a06cd926f5855d4f21fb4bc9978a35312f815fbda0d0ef7fdc846861f4fc4600", 
+      "iso_checksum": "0a03608988cfd2e50567990dc8be96fb3c501e198e2e6efcb846d89efc7b89f2", 
       "boot_wait": "10s", 
       "http_directory": "http", 
       "headless": true, 
@@ -93,7 +93,7 @@
     }, 
     {
       "guest_additions_path": "VBoxGuestAdditions_{{.Version}}.iso", 
-      "iso_url": "http://releases.ubuntu.com/16.04/ubuntu-16.04.3-server-amd64.iso", 
+      "iso_url": "http://releases.ubuntu.com/16.04/ubuntu-16.04.4-server-amd64.iso", 
       "ssh_port": 22, 
       "ssh_username": "{{ user `username` }}", 
       "iso_checksum_type": "sha256", 
@@ -146,7 +146,7 @@
       ], 
       "guest_os_type": "Ubuntu_64", 
       "name": "virtualbox-iso-vagrant", 
-      "iso_checksum": "a06cd926f5855d4f21fb4bc9978a35312f815fbda0d0ef7fdc846861f4fc4600", 
+      "iso_checksum": "0a03608988cfd2e50567990dc8be96fb3c501e198e2e6efcb846d89efc7b89f2", 
       "boot_wait": "10s", 
       "http_directory": "http", 
       "headless": true, 
@@ -286,4 +286,4 @@
       ]
     }
   ]
-}
+}
\ No newline at end of file
diff --git a/packer.yaml b/packer.yaml
index 97cc718..b08ee92 100644
--- a/packer.yaml
+++ b/packer.yaml
@@ -54,9 +54,9 @@ builders:
   guest_os_type: Ubuntu_64
   headless: true
   http_directory: http
-  iso_checksum: a06cd926f5855d4f21fb4bc9978a35312f815fbda0d0ef7fdc846861f4fc4600
+  iso_checksum: 0a03608988cfd2e50567990dc8be96fb3c501e198e2e6efcb846d89efc7b89f2
   iso_checksum_type: sha256
-  iso_url: http://releases.ubuntu.com/16.04/ubuntu-16.04.3-server-amd64.iso
+  iso_url: http://releases.ubuntu.com/16.04/ubuntu-16.04.4-server-amd64.iso
   shutdown_command: echo 'shutdown -P now' > shutdown.sh; echo '{{ user `username` }}'|sudo -S sh 'shutdown.sh'
   ssh_password: '{{ user `password` }}'
   ssh_port: 22
diff --git a/roles/galaxyprojectdotorg.devbox/tasks/main.yml b/roles/galaxyprojectdotorg.devbox/tasks/main.yml
index 484443a..320003e 100644
--- a/roles/galaxyprojectdotorg.devbox/tasks/main.yml
+++ b/roles/galaxyprojectdotorg.devbox/tasks/main.yml
@@ -125,10 +125,10 @@
   become_user: "{{ dev_user_name }}"
   shell: "virtualenv {{ dev_planemo_virtualenv }}"
 
-- name: Install planemo
+- name: Install planemo and optional dependencies
   become: True
   become_user: "{{ dev_user_name }}"
-  shell: ". {{ dev_planemo_virtualenv }}/bin/activate && pip install planemo"
+  shell: ". {{ dev_planemo_virtualenv }}/bin/activate && pip install toil && pip install planemo"
 
 - name: Setup planemo virtualenv on PATH
   lineinfile: "dest={{ dev_user_shellrc }} line='export PATH=$PATH:{{ dev_planemo_virtualenv }}/bin'"
diff --git a/roles/galaxyprojectdotorg.devbox/templates/check-planemo-machine.sh.j2 b/roles/galaxyprojectdotorg.devbox/templates/check-planemo-machine.sh.j2
index 2b81cf9..883f69d 100644
--- a/roles/galaxyprojectdotorg.devbox/templates/check-planemo-machine.sh.j2
+++ b/roles/galaxyprojectdotorg.devbox/templates/check-planemo-machine.sh.j2
@@ -1,4 +1,4 @@
-#/bin/sh
+#/bin/bash
 
 set -e
 
@@ -40,10 +40,17 @@ supervisorctl status nginx | grep -q RUNNING
 echo "Checking GIE proxy is running."
 supervisorctl status galaxy:galaxy_nodejs_proxy | grep -q RUNNING
 
-## TODO: Move linuxbrew & miniconda stuff from .bashrc to .profile I guess?
+## TODO: Move miniconda stuff from .bashrc to .profile I guess?
 ## su -l {{ dev_user_name }} /bin/bash -c 'planemo --help'
 su -l {{ dev_user_name }} /bin/bash -c '{{ dev_planemo_virtualenv }}/bin/planemo --help'
 
+DOC_TEST_RUNNER="https://raw.githubusercontent.com/galaxyproject/planemo/master/scripts/run_doc_test.sh"
+curl -s "$DOC_TEST_RUNNER" > /tmp/run_doc_test.sh
+su -l {{ dev_user_name }} /bin/bash -c "PLANEMO_VIRTUAL_ENV={{ dev_planemo_virtualenv }} DOCS=building bash /tmp/run_doc_test.sh"
+su -l {{ dev_user_name }} /bin/bash -c "PLANEMO_VIRTUAL_ENV={{ dev_planemo_virtualenv }} DOCS=building_cwl bash /tmp/run_doc_test.sh"
+su -l {{ dev_user_name }} /bin/bash -c "PLANEMO_VIRTUAL_ENV={{ dev_planemo_virtualenv }} DOCS=conda bash /tmp/run_doc_test.sh"
+su -l {{ dev_user_name }} /bin/bash -c "PLANEMO_VIRTUAL_ENV={{ dev_planemo_virtualenv }} DOCS=conda_cwl bash /tmp/run_doc_test.sh"
+
 ## TODO: Check Conda in the future.
 # echo "Checking if Docker is running."
 # docker ps