diff --git a/roles/ensure_os_upgrade/tasks/Debian-default.yml b/roles/ensure_os_upgrade/tasks/Debian-default.yml
new file mode 100644
index 0000000..c3dba9f
--- /dev/null
+++ b/roles/ensure_os_upgrade/tasks/Debian-default.yml
@@ -0,0 +1,54 @@
+---
+# tasks file for ensure_os_upgrade - Debian
+- name: Update sources.list for Debian Upgrade
+  when:
+    - ansible_facts["system"] == 'Linux'
+    - ansible_facts["os_family"] == 'Debian'
+    - ensure_os_upgrade is defined
+    - ensure_os_upgrade.target_codename is defined
+  ansible.builtin.replace:
+    path: /etc/apt/sources.list
+    regexp: '^(deb(?:-src)?\s+https?://[a-zA-Z0-9.-]*debian\.org\S*\s+)\b{{ ansible_facts["lsb"]["codename"] }}\b(.*)$'
+    replace: '\1{{ ensure_os_upgrade.target_codename }}\2'
+    backup: yes
+
+- name: Safe Upgrade Debian Packages
+  when:
+    - ansible_facts["system"] == 'Linux'
+    - ansible_facts["os_family"] == 'Debian'
+    - ensure_os_upgrade is defined
+    - ensure_os_upgrade.target_codename is defined
+  ansible.builtin.apt:
+    update_cache: yes
+    upgrade: safe
+    dpkg_options: 'force-confnew,force-confdef'
+  environment:
+    DEBIAN_FRONTEND: noninteractive
+
+- name: Full Upgrade Debian Packages
+  when:
+    - ansible_facts["system"] == 'Linux'
+    - ansible_facts["os_family"] == 'Debian'
+    - ensure_os_upgrade is defined
+    - ensure_os_upgrade.target_codename is defined
+  ansible.builtin.apt:
+    upgrade: dist
+    dpkg_options: 'force-confnew,force-confdef'
+    autoremove: yes
+    autoclean: yes
+  environment:
+    DEBIAN_FRONTEND: noninteractive
+
+- name: Reboot Debian After Upgrade
+  when:
+    - ansible_facts["system"] == 'Linux'
+    - ansible_facts["os_family"] == 'Debian'
+    - ensure_os_upgrade is defined
+    - ensure_os_upgrade.target_codename is defined
+  ansible.builtin.reboot:
+    msg: "Rebooting for OS Upgrade"
+    connect_timeout: 5
+    reboot_timeout: 1800
+    pre_reboot_delay: 5
+    post_reboot_delay: 15
+    test_command: whoami
diff --git a/roles/ensure_os_upgrade/tasks/Fedora-default.yml b/roles/ensure_os_upgrade/tasks/Fedora-default.yml
new file mode 100644
index 0000000..cbd3e14
--- /dev/null
+++ b/roles/ensure_os_upgrade/tasks/Fedora-default.yml
@@ -0,0 +1,45 @@
+---
+# tasks file for ensure_os_upgrade - Fedora
+- name: Ensure System-upgrade Download
+  when:
+    - ansible_facts["system"] == 'Linux'
+    - ansible_facts["distribution"] == 'Fedora'
+    - ensure_os_upgrade is defined
+    - ensure_os_upgrade.package_list is defined
+    - ensure_os_upgrade.package_list is iterable
+    - ensure_os_upgrade.target_version is defined
+    - ansible_facts["distribution_major_version"]|int < ensure_os_upgrade.target_version|int
+  ansible.builtin.shell: >
+    dnf -y system-upgrade download --refresh --releasever={{ ensure_os_upgrade.target_version|int }}
+- name: Ensure System-upgrade Reboot
+  when:
+    - ansible_facts["system"] == 'Linux'
+    - ansible_facts["distribution"] == 'Fedora'
+    - ensure_os_upgrade is defined
+    - ensure_os_upgrade.package_list is defined
+    - ensure_os_upgrade.package_list is iterable
+    - ensure_os_upgrade.target_version is defined
+    - ansible_facts["distribution_major_version"]|int < ensure_os_upgrade.target_version|int
+  async: 1
+  poll: 0
+  ansible.builtin.shell: >
+    sleep 5 && dnf -y system-upgrade reboot
+- name: Wait For The Reboot
+  when:
+    - ansible_facts["system"] == 'Linux'
+    - ansible_facts["distribution"] == 'Fedora'
+    - ensure_os_upgrade is defined
+    - ensure_os_upgrade.package_list is defined
+    - ensure_os_upgrade.package_list is iterable
+    - ensure_os_upgrade.target_version is defined
+    - ansible_facts["distribution_major_version"]|int < ensure_os_upgrade.target_version|int
+  ansible.builtin.wait_for:
+    connect_timeout: '5'
+    delay: '300'
+    host: '{{ (ansible_ssh_host|default(ansible_host))|default(inventory_hostname) }}'
+    port: '22'
+    search_regex: OpenSSH
+    sleep: '15'
+    timeout: '1800'
+  vars:
+    ansible_connection: local
diff --git a/roles/ensure_os_upgrade/tasks/Ubuntu-default.yml b/roles/ensure_os_upgrade/tasks/Ubuntu-default.yml
new file mode 100644
index 0000000..ecdb815
--- /dev/null
+++ b/roles/ensure_os_upgrade/tasks/Ubuntu-default.yml
@@ -0,0 +1,48 @@
+---
+# tasks file for ensure_os_upgrade - Ubuntu
+- name: Ensure update-manager-core is installed
+  when:
+    - ansible_facts["system"] == 'Linux'
+    - ansible_facts["distribution"] == 'Ubuntu'
+    - ensure_os_upgrade is defined
+  ansible.builtin.apt:
+    name: update-manager-core
+    state: present
+
+- name: Configure Ubuntu Release Upgrade Prompt
+  when:
+    - ansible_facts["system"] == 'Linux'
+    - ansible_facts["distribution"] == 'Ubuntu'
+    - ensure_os_upgrade is defined
+    - ensure_os_upgrade.target_version is defined
+  ansible.builtin.lineinfile:
+    path: /etc/update-manager/release-upgrades
+    regexp: '^Prompt='
+    line: "Prompt={{ 'lts' if ensure_os_upgrade.target_version.endswith('.04') else 'normal' }}"
+
+- name: Execute Ubuntu Release Upgrade
+  when:
+    - ansible_facts["system"] == 'Linux'
+    - ansible_facts["distribution"] == 'Ubuntu'
+    - ensure_os_upgrade is defined
+    - ensure_os_upgrade.target_version is defined
+    - ansible_facts["distribution_version"] != ensure_os_upgrade.target_version
+  ansible.builtin.command: do-release-upgrade -f DistUpgradeViewNonInteractive
+  environment:
+    DEBIAN_FRONTEND: noninteractive
+    DPKG_OPTIONS: '-o Dpkg::Options::="--force-confnew" -o Dpkg::Options::="--force-confdef"'
+
+- name: Reboot Ubuntu After Upgrade
+  when:
+    - ansible_facts["system"] == 'Linux'
+    - ansible_facts["distribution"] == 'Ubuntu'
+    - ensure_os_upgrade is defined
+    - ensure_os_upgrade.target_version is defined
+    - ansible_facts["distribution_version"] != ensure_os_upgrade.target_version
+  ansible.builtin.reboot:
+    msg: "Rebooting for OS Upgrade"
+    connect_timeout: 5
+    reboot_timeout: 1800
+    pre_reboot_delay: 5
+    post_reboot_delay: 15
+    test_command: whoami
diff --git a/roles/ensure_os_upgrade/tasks/main.yml b/roles/ensure_os_upgrade/tasks/main.yml
index 9f0a78e..f6bbfb8 100644
--- a/roles/ensure_os_upgrade/tasks/main.yml
+++ b/roles/ensure_os_upgrade/tasks/main.yml
@@ -62,49 +62,25 @@
   notify:
     - Ensure_Os_Upgrade.Package_Facts
     - Ensure_Os_Upgrade.Service_Facts
-- name: Ensure System-upgrade Download
-  when:
-    - ansible_facts["system"] == 'Linux'
-    - ansible_facts["distribution"] == 'Fedora'
-    - ensure_os_upgrade is defined
-    - ensure_os_upgrade.package_list is defined
-    - ensure_os_upgrade.package_list is iterable
-    - ensure_os_upgrade.target_version is defined
-    - ansible_facts["distribution_major_version"]|int < ensure_os_upgrade.target_version|int
-  ansible.builtin.shell: >
-    dnf -y system-upgrade download --refresh --releasever={{ ensure_os_upgrade.target_version|int }}
-- name: Ensure System-upgrade Reboot
-  when:
-    - ansible_facts["system"] == 'Linux'
-    - ansible_facts["distribution"] == 'Fedora'
-    - ensure_os_upgrade is defined
-    - ensure_os_upgrade.package_list is defined
-    - ensure_os_upgrade.package_list is iterable
-    - ensure_os_upgrade.target_version is defined
-    - ansible_facts["distribution_major_version"]|int < ensure_os_upgrade.target_version|int
-  async: 1
-  poll: 0
-  ansible.builtin.shell: >
-    sleep 5 && dnf -y system-upgrade reboot
-- name: Wait For The Reboot
-  when:
-    - ansible_facts["system"] == 'Linux'
-    - ansible_facts["distribution"] == 'Fedora'
-    - ensure_os_upgrade is defined
-    - ensure_os_upgrade.package_list is defined
-    - ensure_os_upgrade.package_list is iterable
-    - ensure_os_upgrade.target_version is defined
-    - ansible_facts["distribution_major_version"]|int < ensure_os_upgrade.target_version|int
-  ansible.builtin.wait_for:
-    connect_timeout: '5'
-    delay: '300'
-    host: '{{ (ansible_ssh_host|default(ansible_host))|default(inventory_hostname) }}'
-    port: '22'
-    search_regex: OpenSSH
-    sleep: '15'
-    timeout: '1800'
+- name: Include Vendor / Version Specific Tasks
+  when: ["ansible_facts[\"system\"] == 'Linux'"]
+  ansible.builtin.include_tasks:
+    file: '{{ lookup("first_found", findme) }}'
   vars:
-    ansible_connection: local
+    findme:
+      files:
+        - '{{ ansible_facts["distribution"] }}-{{ ansible_facts["distribution_major_version"]
+          }}-{{ ansible_facts["architecture"] }}.yml'
+        - '{{ ansible_facts["distribution"] }}-{{ ansible_facts["distribution_major_version"]
+          }}-default.yml'
+        - '{{ ansible_facts["distribution"] }}-default.yml'
+        - '{{ ansible_facts["os_family"] }}-{{ ansible_facts["distribution_major_version"]
+          }}-{{ ansible_facts["architecture"] }}.yml'
+        - '{{ ansible_facts["os_family"] }}-{{ ansible_facts["distribution_major_version"]
+          }}-default.yml'
+        - '{{ ansible_facts["os_family"] }}-default.yml'
+        - default.yml
+      errors: ignore
 - name: Gather Facts
   ansible.builtin.setup:
   notify:
diff --git a/roles/ensure_os_upgrade/vars/Debian-11-default.yml b/roles/ensure_os_upgrade/vars/Debian-11-default.yml
new file mode 100644
index 0000000..5cb3e43
--- /dev/null
+++ b/roles/ensure_os_upgrade/vars/Debian-11-default.yml
@@ -0,0 +1,4 @@
+---
+# vars file for ensure_os_upgrade - Debian 11 (Bullseye)
+# Goal: Upgrade to oldest in-support version (Debian 12 Bookworm)
+target_codename: 'bookworm'
diff --git a/roles/ensure_os_upgrade/vars/Debian-12-default.yml b/roles/ensure_os_upgrade/vars/Debian-12-default.yml
new file mode 100644
index 0000000..579b89d
--- /dev/null
+++ b/roles/ensure_os_upgrade/vars/Debian-12-default.yml
@@ -0,0 +1,4 @@
+---
+# vars file for ensure_os_upgrade - Debian 12 (Bookworm)
+# Currently in-support. No automatic upgrade to Debian 13 (Trixie).
+# target_codename: 'trixie'
diff --git a/roles/ensure_os_upgrade/vars/Ubuntu-20-default.yml b/roles/ensure_os_upgrade/vars/Ubuntu-20-default.yml
new file mode 100644
index 0000000..f0f007a
--- /dev/null
+++ b/roles/ensure_os_upgrade/vars/Ubuntu-20-default.yml
@@ -0,0 +1,4 @@
+---
+# vars file for ensure_os_upgrade - Ubuntu 20.04 (Focal Fossa)
+# Goal: Upgrade to oldest in-support version (Ubuntu 22.04 LTS)
+target_version: '22.04'
diff --git a/roles/ensure_os_upgrade/vars/Ubuntu-22-default.yml b/roles/ensure_os_upgrade/vars/Ubuntu-22-default.yml
new file mode 100644
index 0000000..d438658
--- /dev/null
+++ b/roles/ensure_os_upgrade/vars/Ubuntu-22-default.yml
@@ -0,0 +1,4 @@
+---
+# vars file for ensure_os_upgrade - Ubuntu 22.04 (Jammy Jellyfish)
+# Currently in-support LTS. No automatic upgrade to 24.04.
+# target_version: '24.04'
diff --git a/roles/ensure_os_upgrade/vars/Ubuntu-24-default.yml b/roles/ensure_os_upgrade/vars/Ubuntu-24-default.yml
new file mode 100644
index 0000000..7782748
--- /dev/null
+++ b/roles/ensure_os_upgrade/vars/Ubuntu-24-default.yml
@@ -0,0 +1,4 @@
+---
+# vars file for ensure_os_upgrade - Ubuntu 24.04 (Noble Numbat)
+# Currently in-support LTS. No automatic upgrade to 26.04.
+# target_version: '26.04'