diff --git a/playbooks/provision.yaml b/playbooks/provision.yaml
index 923617b..4da5208 100644
--- a/playbooks/provision.yaml
+++ b/playbooks/provision.yaml
@@ -9,57 +9,16 @@
 
 - name: Bootstrap remote ansible environment
   hosts: linux
+  gather_facts: false
   tags:
     - always
   tasks:
-    - name: Install CentOS 8 python bindings
-      when: ansible_distribution == "Rocky"
-      become: true
-      ansible.builtin.dnf:
-        state: present
-        name:
-          - python3-libselinux
-          - python3-policycoreutils
-          - python3-firewall
-
-    - name: Create state directory
-      become: true
-      ansible.builtin.file:
-        path: "{{ skylab_state_dir }}"
-        state: directory
-        owner: "{{ ansible_user }}"
-        group: "{{ ansible_user }}"
-        mode: 0755
-
-    - name: Create bootstrap virtualenv
-      ansible.builtin.command:
-        cmd: "{{ ansible_python_interpeter | default(discovered_interpreter_python) }} -m venv {{ skylab_ansible_venv }} --system-site-packages"
-        creates: "{{ skylab_ansible_venv }}/bin/python"
-
-    - name: Pin bootstrap virtualenv pip
-      ansible.builtin.pip:
-        executable: "{{ skylab_ansible_venv }}/bin/pip"
-        name: pip
-        state: present
-        version: "{{ skylab_pip_version }}"
-
-    - name: Copy requirements file to remote
-      ansible.builtin.copy:
-        src: remote-requirements.txt
-        dest: "{{ skylab_ansible_venv }}/requirements.txt"
-        owner: "{{ ansible_user }}"
-        group: "{{ ansible_user }}"
-        mode: 0644
-
-    - name: Install remote requirements
-      ansible.builtin.pip:
-        executable: "{{ skylab_ansible_venv }}/bin/pip"
-        requirements: "{{ skylab_ansible_venv }}/requirements.txt"
-        state: present
+    - include_tasks: tasks/meta/bootstrap-remote-env.yaml
 
 
-- name: Configure common server settings
+- name: Configure common settings
   hosts: linux
+  gather_facts: false
   vars_files:
     - vars/packages.yaml
   tasks:
@@ -69,6 +28,15 @@
         name: "{{ inventory_hostname }}"
         use: systemd
 
+    - name: Install global bash config
+      become: true
+      ansible.builtin.copy:
+        src: global.sh
+        dest: /etc/profile.d/ZZ-skylab-global.sh
+        owner: root
+        group: "{{ ansible_user }}"
+        mode: 0644
+
     - name: Install EPEL repository config
       when: ansible_distribution == "Rocky"
       become: true
@@ -84,25 +52,6 @@
         state: present
         key: https://archive.fedoraproject.org/pub/epel/RPM-GPG-KEY-EPEL-{{ ansible_distribution_major_version }}
 
-    - name: Disable sudo password for WHEEL group
-      when: ansible_distribution == "Rocky" or ansible_distribution == "CentOS"
-      become: true
-      ansible.builtin.copy:
-        src: wheel-group-no-sudo-password
-        dest: /etc/sudoers.d/30-wheel
-        owner: root
-        group: "{{ ansible_user }}"
-        mode: 0644
-
-    - name: Install global bash config
-      become: true
-      ansible.builtin.copy:
-        src: global.sh
-        dest: /etc/profile.d/ZZ-skylab-global.sh
-        owner: root
-        group: "{{ ansible_user }}"
-        mode: 0644
-
     - name: Install universal packages
       when: ansible_distribution == "Rocky"
       become: true
@@ -111,58 +60,7 @@
         state: present
 
 
-- name: Configure SSH
-  hosts: linux
-  handlers:
-    - name: restart-sshd
-      become: true
-      ansible.builtin.systemd:
-        name: sshd
-        state: restarted
-  tasks:
-    - name: Configure SSH authentication settings
-      become: true
-      ansible.builtin.replace:
-        path: /etc/ssh/sshd_config
-        regexp: "{{ item.regex }}"
-        replace: "{{ item.value }}"
-      notify: [restart-sshd]
-      loop:
-        - name: disable root login
-          regex: "^.*PermitRootLogin (yes|no).*$"
-          value: PermitRootLogin no
-        - name: disable password auth
-          regex: "^.*PasswordAuthentication (yes|no).*$"
-          value: PasswordAuthentication no
-        - name: disable challenge response auth
-          regex: "^.*ChallengeResponseAuthentication (yes|no).*$"
-          value: ChallengeResponseAuthentication no
-        - name: disable GSSAPI auth
-          regex: "^.*GSSAPIAuthentication (yes|no).*$"
-          value: GSSAPIAuthentication no
-      loop_control:
-        label: "{{ item.name }}"
-
-    - name: Disable dynamic MOTD on debian systems
-      when: ansible_os_family == "Debian"
-      ansible.builtin.replace:
-        path: /etc/pam.d/sshd
-        regexp: "^session    optional     pam_motd.so  motd=/run/motd.dynamic"
-        replace: "#session    optional     pam_motd.so  motd=/run/motd.dynamic"
-
-    - name: Disable Cockpit activation message on Rocky
-      when: ansible_distribution == "Rocky"
-      become: true
-      ansible.builtin.file:
-        path: /etc/motd.d/cockpit
-        state: absent
-
-    - name: Copy MOTD to remote
-      become: true
-      ansible.builtin.template:
-        src: motd.j2
-        dest: /etc/motd
-        mode: 0644
-
-
 - import_playbook: update.yaml
+
+
+- import_playbook: configure.yaml
diff --git a/playbooks/roles b/playbooks/roles
new file mode 120000
index 0000000..d8c4472
--- /dev/null
+++ b/playbooks/roles
@@ -0,0 +1 @@
+../roles
\ No newline at end of file
diff --git a/playbooks/update.yaml b/playbooks/update.yaml
index d3ae92e..d1e918a 100644
--- a/playbooks/update.yaml
+++ b/playbooks/update.yaml
@@ -7,6 +7,15 @@
     - include_tasks: tasks/meta/runtime-group-determination.yaml
 
 
+- name: Bootstrap remote ansible environment
+  hosts: linux
+  gather_facts: false
+  tags:
+    - always
+  tasks:
+    - include_tasks: tasks/meta/bootstrap-remote-env.yaml
+
+
 - name: Update system
   hosts: linux
   tags:
diff --git a/resources/wheel-group-no-sudo-password b/roles/server/files/wheel-group-no-sudo-password
similarity index 100%
rename from resources/wheel-group-no-sudo-password
rename to roles/server/files/wheel-group-no-sudo-password
diff --git a/roles/server/handlers/main.yaml b/roles/server/handlers/main.yaml
new file mode 100644
index 0000000..ba12abf
--- /dev/null
+++ b/roles/server/handlers/main.yaml
@@ -0,0 +1,6 @@
+---
+- name: restart-sshd
+  become: true
+  ansible.builtin.systemd:
+    name: sshd
+    state: restarted
diff --git a/roles/server/tasks/main.yaml b/roles/server/tasks/main.yaml
new file mode 100644
index 0000000..e2fe4c1
--- /dev/null
+++ b/roles/server/tasks/main.yaml
@@ -0,0 +1,6 @@
+---
+- name: Configure sudoers file
+  ansible.builtin.import_tasks: sudoers.yaml
+
+- name: Configure SSH server
+  ansible.builtin.import_tasks: sshd.yaml
diff --git a/roles/server/tasks/sshd.yaml b/roles/server/tasks/sshd.yaml
new file mode 100644
index 0000000..244182c
--- /dev/null
+++ b/roles/server/tasks/sshd.yaml
@@ -0,0 +1,44 @@
+---
+- name: Configure SSH authentication settings
+  become: true
+  ansible.builtin.replace:
+    path: /etc/ssh/sshd_config
+    regexp: "{{ item.regex }}"
+    replace: "{{ item.value }}"
+  notify: [restart-sshd]
+  loop:
+    - name: disable root login
+      regex: "^.*PermitRootLogin (yes|no).*$"
+      value: PermitRootLogin no
+    - name: disable password auth
+      regex: "^.*PasswordAuthentication (yes|no).*$"
+      value: PasswordAuthentication no
+    - name: disable challenge response auth
+      regex: "^.*ChallengeResponseAuthentication (yes|no).*$"
+      value: ChallengeResponseAuthentication no
+    - name: disable GSSAPI auth
+      regex: "^.*GSSAPIAuthentication (yes|no).*$"
+      value: GSSAPIAuthentication no
+  loop_control:
+    label: "{{ item.name }}"
+
+- name: Disable dynamic MOTD on debian systems
+  when: ansible_os_family == "Debian"
+  ansible.builtin.replace:
+    path: /etc/pam.d/sshd
+    regexp: "^session    optional     pam_motd.so  motd=/run/motd.dynamic"
+    replace: "#session    optional     pam_motd.so  motd=/run/motd.dynamic"
+
+- name: Disable Cockpit activation message on Rocky
+  when: ansible_distribution == "Rocky"
+  become: true
+  ansible.builtin.file:
+    path: /etc/motd.d/cockpit
+    state: absent
+
+- name: Copy MOTD to remote
+  become: true
+  ansible.builtin.template:
+    src: motd.j2
+    dest: /etc/motd
+    mode: 0644
diff --git a/roles/server/tasks/sudoers.yaml b/roles/server/tasks/sudoers.yaml
new file mode 100644
index 0000000..c5767f1
--- /dev/null
+++ b/roles/server/tasks/sudoers.yaml
@@ -0,0 +1,30 @@
+---
+- name: Disable sudo password for WHEEL group
+  when: ansible_distribution == "Rocky" or ansible_distribution == "CentOS"
+  become: true
+  ansible.builtin.copy:
+    src: wheel-group-no-sudo-password
+    dest: /etc/sudoers.d/30-wheel
+    owner: root
+    group: "{{ ansible_user }}"
+    mode: 0644
+
+# Note that the cleanup tasks need to be after the new installation tasks
+# since one or more files being cleaned up might be being relied on to
+# allow ansible access
+- name: Fetch content of sudoers config directory
+  become: true
+  changed_when: false
+  ansible.builtin.command:
+    cmd: /usr/bin/ls /etc/sudoers.d/
+  register: _sudoers_files_raw
+
+- name: Remove legacy sudoers config files
+  when: item.strip() not in ["30-wheel"]
+  become: true
+  ansible.builtin.file:
+    path: /etc/sudoers.d/{{ item.strip() }}
+    state: absent
+  loop: "{{ _sudoers_files_raw.stdout.split(' ') }}"
+  loop_control:
+    label: "/etc/sudoers.d/{{ item.strip() }}"
diff --git a/resources/motd.j2 b/roles/server/templates/motd.j2
similarity index 100%
rename from resources/motd.j2
rename to roles/server/templates/motd.j2