diff --git a/changelogs/fragments/agent.yml b/changelogs/fragments/agent.yml
index f18339599..84cbbeb11 100644
--- a/changelogs/fragments/agent.yml
+++ b/changelogs/fragments/agent.yml
@@ -1,2 +1,4 @@
 minor_changes:
   - Agent role - Allow the role to download folder-specific agents.
+bugfixes:
+  - Agent role - Fix agent and update registration on remote sites.
diff --git a/roles/agent/tasks/Debian.yml b/roles/agent/tasks/Debian.yml
index 67b61f986..6f67bfca4 100644
--- a/roles/agent/tasks/Debian.yml
+++ b/roles/agent/tasks/Debian.yml
@@ -1,5 +1,5 @@
 ---
-- name: "{{ ansible_os_family }} Derivatives: Download host-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Download host-specific {{ checkmk_agent_edition | upper }} Agent."
   ansible.builtin.uri:
     url: "{{ checkmk_agent_agent.url.cee }}?host_name={{ checkmk_agent_host_name }}&os_type=linux_deb&agent_type=host_name"
     validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
@@ -9,10 +9,7 @@
       Authorization: "Bearer {{ checkmk_agent_user }} {{ checkmk_agent_auth }}"
       Accept: "application/octet-stream"
   when: |
-    checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme"
+    checkmk_agent_edition | lower != "cre"
   become: false
   register: checkmk_agent_host_download_state
   # This task may fail, as we fall back to the generic agent in that case
@@ -27,37 +24,31 @@
     checkmk_agent_host_specific: >-
      {{ (checkmk_agent_host_download_state.status is defined and checkmk_agent_host_download_state.status == 200) | bool }}
 
-- name: "{{ ansible_os_family }} Derivatives: Transfer host-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Transfer host-specific {{ checkmk_agent_edition | upper }} Agent."
   ansible.builtin.copy:
     src: "{{ checkmk_agent_agent.file.host }}"
     dest: "{{ checkmk_agent_agent.file.host }}"
     mode: "0644"
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and checkmk_agent_host_specific | bool
     and checkmk_agent_delegate_download != inventory_hostname
   tags:
     - download-package
 
-- name: "{{ ansible_os_family }} Derivatives: Install host-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Install host-specific {{ checkmk_agent_edition | upper }} Agent."
   become: true
   ansible.builtin.apt:
     deb: "{{ checkmk_agent_agent.file.host }}"
     force: "{{ checkmk_agent_force_install | bool }}"
     state: present
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and checkmk_agent_host_specific | bool
   tags:
     - install-package
 
-- name: "{{ ansible_os_family }} Derivatives: Download folder-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Download folder-specific {{ checkmk_agent_edition | upper }} Agent."
   ansible.builtin.uri:
     url: "{{ checkmk_agent_agent.url.cee }}?os_type=linux_deb&agent_type=generic&folder_name={{ checkmk_agent_folder }}"
     validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
@@ -69,10 +60,7 @@
   become: false
   register: checkmk_agent_folder_download_state
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and checkmk_agent_folder is defined
     and not checkmk_agent_host_specific | bool
   retries: 3
@@ -87,7 +75,7 @@
     checkmk_agent_folder_specific: >-
      {{ (checkmk_agent_folder_download_state.status is defined and checkmk_agent_folder_download_state.status == 200) | bool }}
 
-- name: "{{ ansible_os_family }} Derivatives: Download GENERIC Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Download GENERIC {{ checkmk_agent_edition | upper }} Agent."
   ansible.builtin.uri:
     url: "{{ checkmk_agent_agent.url.cee }}?os_type=linux_deb&agent_type=generic"
     validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
@@ -98,52 +86,54 @@
       Accept: "application/octet-stream"
   become: false
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and not (checkmk_agent_host_specific | bool or checkmk_agent_folder_specific | bool)
   retries: 3
   delegate_to: "{{ checkmk_agent_delegate_download }}"
   tags:
     - download-package
 
-- name: "{{ ansible_os_family }} Derivatives: Transfer GENERIC or folder-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Transfer GENERIC or folder-specific {{ checkmk_agent_edition | upper }} Agent."
   ansible.builtin.copy:
     src: "{{ checkmk_agent_agent.file.cee }}"
     dest: "{{ checkmk_agent_agent.file.cee }}"
     mode: "0644"
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and not checkmk_agent_host_specific | bool
     and checkmk_agent_delegate_download != inventory_hostname
   tags:
     - download-package
 
-- name: "{{ ansible_os_family }} Derivatives: Install GENERIC or folder-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Install GENERIC or folder-specific {{ checkmk_agent_edition | upper }} Agent."
   become: true
   ansible.builtin.apt:
     deb: "{{ checkmk_agent_agent.file.cee }}"
     force: "{{ checkmk_agent_force_install | bool }}"
     state: present
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and not checkmk_agent_host_specific | bool
   tags:
     - install-package
 
-- name: "{{ ansible_os_family }} Derivatives: Install Checkmk CRE Agent."
+- name: "{{ ansible_os_family }} Derivatives: Transfer Vanilla {{ checkmk_agent_edition | upper }} Agent."
+  ansible.builtin.copy:
+    src: "{{ checkmk_agent_agent.file.cre }}"
+    dest: "{{ checkmk_agent_agent.file.cre }}"
+    mode: "0644"
+  when: |
+    checkmk_agent_edition | lower == "cre"
+    and checkmk_agent_delegate_download != inventory_hostname
+  tags:
+    - download-package
+
+- name: "{{ ansible_os_family }} Derivatives: Install Vanilla {{ checkmk_agent_edition | upper }} Agent."
   become: true
   ansible.builtin.apt:
     deb: "{{ checkmk_agent_agent.file.cre }}"
     force: "{{ checkmk_agent_force_install | bool }}"
     state: present
-  when: checkmk_agent_edition == "cre"
+  when: checkmk_agent_edition | lower == "cre"
   tags:
     - install-package
diff --git a/roles/agent/tasks/Linux.yml b/roles/agent/tasks/Linux.yml
index 6e4eb5d8c..d6a4c81e1 100644
--- a/roles/agent/tasks/Linux.yml
+++ b/roles/agent/tasks/Linux.yml
@@ -14,17 +14,18 @@
     checkmk_agent_prep_legacy | bool
     and ansible_facts.packages['systemd'][0]['version'] | regex_search('\d{1,}') | int < 220
 
-- name: "{{ ansible_system }}: Download Checkmk CRE agent."
+- name: "{{ ansible_system }}: Download Vanilla {{ checkmk_agent_edition | upper }} agent."
   ansible.builtin.get_url:
     url: "{{ checkmk_agent_agent.url.cre }}"
     validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
     dest: "{{ checkmk_agent_agent.file.cre }}"
     mode: '0640'
-  when: checkmk_agent_edition == "cre"
+  when: checkmk_agent_edition | lower == "cre"
   register: result
   retries: 3
   delay: 10
-  until: "result.changed | bool"
+  until: "not result.failed | bool"
+  delegate_to: "{{ checkmk_agent_delegate_download }}"
   tags:
     - download-package
 
@@ -67,13 +68,11 @@
   become: true
   ansible.builtin.shell: |
     cmk-update-agent register -H {{ checkmk_agent_host_name }} \
-    -s {{ checkmk_agent_server }} -i {{ checkmk_agent_site }} -p {{ checkmk_agent_protocol }} \
+    -s {{ checkmk_agent_registration_server }} -i {{ checkmk_agent_registration_site }} -p {{ checkmk_agent_protocol }} \
     -U {{ checkmk_agent_user }} -P {{ checkmk_agent_auth }}
   register: checkmk_agent_update_state
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and checkmk_agent_updater_binary.stat.exists | bool
     and checkmk_agent_update | bool
     and (checkmk_agent_pass is defined and checkmk_agent_pass | length)
@@ -83,13 +82,11 @@
   become: true
   ansible.builtin.shell: |
     cmk-update-agent register -H {{ checkmk_agent_host_name }} \
-    -s {{ checkmk_agent_server }} -i {{ checkmk_agent_site }} -p {{ checkmk_agent_protocol }} \
+    -s {{ checkmk_agent_registration_server }} -i {{ checkmk_agent_registration_site }} -p {{ checkmk_agent_protocol }} \
     -U {{ checkmk_agent_user }} -S {{ checkmk_agent_auth }}
   register: checkmk_agent_update_state
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and checkmk_agent_updater_binary.stat.exists | bool
     and checkmk_agent_update | bool
     and (checkmk_agent_secret is defined and checkmk_agent_secret | length)
@@ -98,7 +95,7 @@
   become: true
   ansible.builtin.shell: |
     cmk-agent-ctl register -H {{ checkmk_agent_host_name }} \
-    -s {{ checkmk_agent_server }} -i {{ checkmk_agent_site }} \
+    -s {{ checkmk_agent_registration_server }} -i {{ checkmk_agent_registration_site }} \
     -U {{ checkmk_agent_user }} -P {{ checkmk_agent_auth }} --trust-cert
   register: checkmk_agent_tls_state
   when: |
diff --git a/roles/agent/tasks/RedHat.yml b/roles/agent/tasks/RedHat.yml
index 9230f2fe5..3b0a33adb 100644
--- a/roles/agent/tasks/RedHat.yml
+++ b/roles/agent/tasks/RedHat.yml
@@ -1,5 +1,5 @@
 ---
-- name: "{{ ansible_os_family }} Derivatives: Download host-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Download host-specific {{ checkmk_agent_edition | upper }} Agent."
   ansible.builtin.uri:
     url: "{{ checkmk_agent_agent.url.cee }}?host_name={{ checkmk_agent_host_name }}&os_type=linux_rpm&agent_type=host_name"
     validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
@@ -9,10 +9,7 @@
       Authorization: "Bearer {{ checkmk_agent_user }} {{ checkmk_agent_auth }}"
       Accept: "application/octet-stream"
   when: |
-    checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme"
+    checkmk_agent_edition | lower != "cre"
   become: false
   register: checkmk_agent_host_download_state
   # This task may fail, as we fall back to the generic agent in that case
@@ -27,37 +24,31 @@
     checkmk_agent_host_specific: >-
      {{ (checkmk_agent_host_download_state.status is defined and checkmk_agent_host_download_state.status == 200) | bool }}
 
-- name: "{{ ansible_os_family }} Derivatives: Transfer host-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Transfer host-specific {{ checkmk_agent_edition | upper }} Agent."
   ansible.builtin.copy:
     src: "{{ checkmk_agent_agent.file.host }}"
     dest: "{{ checkmk_agent_agent.file.host }}"
     mode: "0644"
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and checkmk_agent_host_specific | bool
     and checkmk_agent_delegate_download != inventory_hostname
   tags:
     - download-package
 
-- name: "{{ ansible_os_family }} Derivatives: Install host-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Install host-specific {{ checkmk_agent_edition | upper }} Agent."
   become: true
   ansible.builtin.yum:
     name: "{{ checkmk_agent_agent.file.host }}"
     state: present
     disable_gpg_check: true
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and checkmk_agent_host_specific | bool
   tags:
     - install-package
 
-- name: "{{ ansible_os_family }} Derivatives: Download folder-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Download folder-specific {{ checkmk_agent_edition | upper }} Agent."
   ansible.builtin.uri:
     url: "{{ checkmk_agent_agent.url.cee }}?os_type=linux_rpm&agent_type=generic&folder_name={{ checkmk_agent_folder }}"
     validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
@@ -69,10 +60,7 @@
   become: false
   register: checkmk_agent_folder_download_state
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and checkmk_agent_folder is defined
     and not checkmk_agent_host_specific | bool
   retries: 3
@@ -87,7 +75,7 @@
     checkmk_agent_folder_specific: >-
      {{ (checkmk_agent_folder_download_state.status is defined and checkmk_agent_folder_download_state.status == 200) | bool }}
 
-- name: "{{ ansible_os_family }} Derivatives: Download GENERIC Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Download GENERIC {{ checkmk_agent_edition | upper }} Agent."
   ansible.builtin.uri:
     url: "{{ checkmk_agent_agent.url.cee }}?os_type=linux_rpm&agent_type=generic"
     validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
@@ -98,53 +86,55 @@
       Accept: "application/octet-stream"
   become: false
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and not (checkmk_agent_host_specific | bool or checkmk_agent_folder_specific | bool)
   retries: 3
   delegate_to: "{{ checkmk_agent_delegate_download }}"
   tags:
     - download-package
 
-- name: "{{ ansible_os_family }} Derivatives: Transfer GENERIC or folder-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Transfer GENERIC or folder-specific {{ checkmk_agent_edition | upper }} Agent."
   ansible.builtin.copy:
     src: "{{ checkmk_agent_agent.file.cee }}"
     dest: "{{ checkmk_agent_agent.file.cee }}"
     mode: "0644"
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and not checkmk_agent_host_specific | bool
     and checkmk_agent_delegate_download != inventory_hostname
   tags:
     - download-package
 
-- name: "{{ ansible_os_family }} Derivatives: Install GENERIC or folder-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Install GENERIC or folder-specific {{ checkmk_agent_edition | upper }} Agent."
   become: true
   ansible.builtin.yum:
     name: "{{ checkmk_agent_agent.file.cee }}"
     state: present
     disable_gpg_check: true
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and not checkmk_agent_host_specific | bool
   tags:
     - install-package
 
-- name: "{{ ansible_os_family }} Derivatives: Install Checkmk CRE Agent."
+- name: "{{ ansible_os_family }} Derivatives: Transfer Vanilla {{ checkmk_agent_edition | upper }} Agent."
+  ansible.builtin.copy:
+    src: "{{ checkmk_agent_agent.file.cre }}"
+    dest: "{{ checkmk_agent_agent.file.cre }}"
+    mode: "0644"
+  when: |
+    checkmk_agent_edition | lower == "cre"
+    and checkmk_agent_delegate_download != inventory_hostname
+  tags:
+    - download-package
+
+- name: "{{ ansible_os_family }} Derivatives: Install Vanilla {{ checkmk_agent_edition | upper }} Agent."
   become: true
   ansible.builtin.yum:
     name: "{{ checkmk_agent_agent.file.cre }}"
     state: present
     disable_gpg_check: true
-  when: checkmk_agent_edition == "cre"
+  when: checkmk_agent_edition | lower == "cre"
   tags:
     - install-package
 
diff --git a/roles/agent/tasks/Suse.yml b/roles/agent/tasks/Suse.yml
index afa7d606f..fe68cdd45 100644
--- a/roles/agent/tasks/Suse.yml
+++ b/roles/agent/tasks/Suse.yml
@@ -1,5 +1,5 @@
 ---
-- name: "{{ ansible_os_family }} Derivatives: Download host-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Download host-specific {{ checkmk_agent_edition | upper }} Agent."
   ansible.builtin.uri:
     url: "{{ checkmk_agent_agent.url.cee }}?host_name={{ checkmk_agent_host_name }}&os_type=linux_rpm&agent_type=host_name"
     validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
@@ -9,10 +9,7 @@
       Authorization: "Bearer {{ checkmk_agent_user }} {{ checkmk_agent_auth }}"
       Accept: "application/octet-stream"
   when: |
-    checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme"
+    checkmk_agent_edition | lower != "cre"
   become: false
   register: checkmk_agent_host_download_state
   # This task may fail, as we fall back to the generic agent in that case
@@ -27,22 +24,19 @@
     checkmk_agent_host_specific: >-
      {{ (checkmk_agent_host_download_state.status is defined and checkmk_agent_host_download_state.status == 200) | bool }}
 
-- name: "{{ ansible_os_family }} Derivatives: Transfer host-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Transfer host-specific {{ checkmk_agent_edition | upper }} Agent."
   ansible.builtin.copy:
     src: "{{ checkmk_agent_agent.file.host }}"
     dest: "{{ checkmk_agent_agent.file.host }}"
     mode: "0644"
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and checkmk_agent_host_specific | bool
     and checkmk_agent_delegate_download != inventory_hostname
   tags:
     - download-package
 
-- name: "{{ ansible_os_family }} Derivatives: Install host-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Install host-specific {{ checkmk_agent_edition | upper }} Agent."
   become: true
   community.general.zypper:
     name: "{{ checkmk_agent_agent.file.host }}"
@@ -50,15 +44,12 @@
     state: present
     disable_gpg_check: true
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and checkmk_agent_host_specific | bool
   tags:
     - install-package
 
-- name: "{{ ansible_os_family }} Derivatives: Download folder-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Download folder-specific {{ checkmk_agent_edition | upper }} Agent."
   ansible.builtin.uri:
     url: "{{ checkmk_agent_agent.url.cee }}?os_type=linux_rpm&agent_type=generic&folder_name={{ checkmk_agent_folder }}"
     validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
@@ -70,10 +61,7 @@
   become: false
   register: checkmk_agent_folder_download_state
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and checkmk_agent_folder is defined
     and not checkmk_agent_host_specific | bool
   retries: 3
@@ -88,7 +76,7 @@
     checkmk_agent_folder_specific: >-
      {{ (checkmk_agent_folder_download_state.status is defined and checkmk_agent_folder_download_state.status == 200) | bool }}
 
-- name: "{{ ansible_os_family }} Derivatives: Download GENERIC Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Download GENERIC {{ checkmk_agent_edition | upper }} Agent."
   ansible.builtin.uri:
     url: "{{ checkmk_agent_agent.url.cee }}?os_type=linux_rpm&agent_type=generic"
     validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
@@ -99,32 +87,26 @@
       Accept: "application/octet-stream"
   become: false
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and not (checkmk_agent_host_specific | bool or checkmk_agent_folder_specific | bool)
   retries: 3
   delegate_to: "{{ checkmk_agent_delegate_download }}"
   tags:
     - download-package
 
-- name: "{{ ansible_os_family }} Derivatives: Transfer GENERIC or folder-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Transfer GENERIC or folder-specific {{ checkmk_agent_edition | upper }} Agent."
   ansible.builtin.copy:
     src: "{{ checkmk_agent_agent.file.cee }}"
     dest: "{{ checkmk_agent_agent.file.cee }}"
     mode: "0644"
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and not checkmk_agent_host_specific | bool
     and checkmk_agent_delegate_download != inventory_hostname
   tags:
     - download-package
 
-- name: "{{ ansible_os_family }} Derivatives: Install GENERIC or folder-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Install GENERIC or folder-specific {{ checkmk_agent_edition | upper }} Agent."
   become: true
   community.general.zypper:
     name: "{{ checkmk_agent_agent.file.cee }}"
@@ -132,21 +114,29 @@
     state: present
     disable_gpg_check: true
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and not checkmk_agent_host_specific | bool
   tags:
     - install-package
 
-- name: "{{ ansible_os_family }} Derivatives: Install Checkmk CRE Agent."
+- name: "{{ ansible_os_family }} Derivatives: Transfer Vanilla {{ checkmk_agent_edition | upper }} Agent."
+  ansible.builtin.copy:
+    src: "{{ checkmk_agent_agent.file.cre }}"
+    dest: "{{ checkmk_agent_agent.file.cre }}"
+    mode: "0644"
+  when: |
+    checkmk_agent_edition | lower == "cre"
+    and checkmk_agent_delegate_download != inventory_hostname
+  tags:
+    - download-package
+
+- name: "{{ ansible_os_family }} Derivatives: Install Vanilla {{ checkmk_agent_edition | upper }} Agent."
   become: true
   community.general.zypper:
     name: "{{ checkmk_agent_agent.file.cre }}"
     force: "{{ checkmk_agent_force_install | bool }}"
     state: present
     disable_gpg_check: true
-  when: checkmk_agent_edition == "cre"
+  when: checkmk_agent_edition | lower == "cre"
   tags:
     - install-package
diff --git a/roles/agent/tasks/Win32NT.yml b/roles/agent/tasks/Win32NT.yml
index 4560a0d2c..876b21f78 100644
--- a/roles/agent/tasks/Win32NT.yml
+++ b/roles/agent/tasks/Win32NT.yml
@@ -43,10 +43,7 @@
   args:
     chdir: "C:\\Program Files (x86)\\checkmk\\service\\"
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and checkmk_agent_binary.stat.exists | bool
     and checkmk_agent_update | bool
     and (checkmk_agent_pass is defined and checkmk_agent_pass | length)
@@ -61,10 +58,7 @@
   args:
     chdir: "C:\\Program Files (x86)\\checkmk\\service\\"
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and checkmk_agent_binary.stat.exists | bool
     and checkmk_agent_update | bool
     and (checkmk_agent_secret is defined and checkmk_agent_secret | length)
diff --git a/roles/agent/tasks/Windows.yml b/roles/agent/tasks/Windows.yml
index 04954ff50..5c8750649 100644
--- a/roles/agent/tasks/Windows.yml
+++ b/roles/agent/tasks/Windows.yml
@@ -1,18 +1,18 @@
 ---
-- name: "{{ ansible_os_family }}: Download Checkmk CRE Agent."
+- name: "{{ ansible_os_family }}: Download Vanilla {{ checkmk_agent_edition | upper }} Agent."
   ansible.windows.win_get_url:
     url: "{{ checkmk_agent_agent.url.cre }}"
     validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
     dest: "{{ checkmk_agent_agent.file.cre }}"
-  when: checkmk_agent_edition == "cre"
+  when: checkmk_agent_edition | lower == "cre"
   register: result
   retries: 3
   delay: 10
-  until: "result.changed | bool"
+  until: "not result.failed | bool"
   tags:
     - download-package
 
-- name: "{{ ansible_os_family }}: Download host-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }}: Download host-specific {{ checkmk_agent_edition | upper }} Agent."
   ansible.windows.win_get_url:
     url: "{{ checkmk_agent_agent.url.cee }}?host_name={{ checkmk_agent_host_name }}&os_type=windows_msi&agent_type=host_name"
     validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
@@ -22,10 +22,7 @@
       Authorization: "Bearer {{ checkmk_agent_user }} {{ checkmk_agent_auth }}"
       Accept: "application/octet-stream"
   when: |
-    checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme"
+    checkmk_agent_edition | lower != "cre"
   register: checkmk_agent_host_download_state
   # This task may fail, as we fall back to the generic agent in that case
   failed_when: 'false'
@@ -39,20 +36,17 @@
     checkmk_agent_host_specific: >-
       {{ (checkmk_agent_host_download_state.status_code is defined and checkmk_agent_host_download_state.status_code == 200) | bool }}
 
-- name: "{{ ansible_os_family }}: Install host-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }}: Install host-specific {{ checkmk_agent_edition | upper }} Agent."
   ansible.windows.win_package:
     path: "{{ checkmk_agent_agent.file.host }}"
     state: present
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and checkmk_agent_host_specific | bool
   tags:
     - install-package
 
-- name: "{{ ansible_os_family }} Derivatives: Download folder-specific Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }} Derivatives: Download folder-specific {{ checkmk_agent_edition | upper }} Agent."
   ansible.windows.win_get_url:
     url: "{{ checkmk_agent_agent.url.cee }}?os_type=windows_msi&agent_type=generic&folder_name={{ checkmk_agent_folder }}"
     validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
@@ -63,10 +57,7 @@
       Accept: "application/octet-stream"
   register: checkmk_agent_folder_download_state
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and checkmk_agent_folder is defined
     and not checkmk_agent_host_specific | bool
   retries: 3
@@ -81,7 +72,7 @@
     checkmk_agent_folder_specific: >-
       {{ (checkmk_agent_folder_download_state.status_code is defined and checkmk_agent_folder_download_state.status_code == 200) | bool }}
 
-- name: "{{ ansible_os_family }}: Download GENERIC Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }}: Download GENERIC {{ checkmk_agent_edition | upper }} Agent."
   ansible.windows.win_get_url:
     url: "{{ checkmk_agent_agent.url.cee }}?os_type=windows_msi&agent_type=generic"
     validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
@@ -91,33 +82,27 @@
       Authorization: "Bearer {{ checkmk_agent_user }} {{ checkmk_agent_auth }}"
       Accept: "application/octet-stream"
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and not (checkmk_agent_host_specific | bool or checkmk_agent_folder_specific | bool)
   retries: 3
   delegate_to: "{{ checkmk_agent_delegate_download }}"
   tags:
     - download-package
 
-- name: "{{ ansible_os_family }}: Install GENERIC or folder-specific  Checkmk {{ checkmk_agent_edition | upper }} Agent."
+- name: "{{ ansible_os_family }}: Install GENERIC or folder-specific  {{ checkmk_agent_edition | upper }} Agent."
   ansible.windows.win_package:
     path: "{{ checkmk_agent_agent.file.cee }}"
     state: present
   when: |
-    (checkmk_agent_edition == "cee" or
-    checkmk_agent_edition == "cce" or
-    checkmk_agent_edition == "cfe" or
-    checkmk_agent_edition == "cme")
+    checkmk_agent_edition | lower != "cre"
     and not checkmk_agent_host_specific | bool
   tags:
     - install-package
 
-- name: "{{ ansible_os_family }}: Install Checkmk CRE Agent."
+- name: "{{ ansible_os_family }}: Install Vanilla {{ checkmk_agent_edition | upper }} Agent."
   ansible.windows.win_package:
     path: "{{ checkmk_agent_agent.file.cre }}"
     state: present
-  when: checkmk_agent_edition == "cre"
+  when: checkmk_agent_edition | lower == "cre"
   tags:
     - install-package
diff --git a/roles/agent/tasks/main.yml b/roles/agent/tasks/main.yml
index 57ae2ce1a..bd414bc8f 100644
--- a/roles/agent/tasks/main.yml
+++ b/roles/agent/tasks/main.yml
@@ -1,4 +1,9 @@
 ---
+- name: "Preflight - Fail if Checkmk Edition is incorrect."
+  ansible.builtin.fail:
+    msg: "The provided Checkmk Edition '{{ checkmk_agent_edition }}' does  not exist or is not supported by this role."
+  when: checkmk_agent_edition | lower not in checkmk_agent_edition_mapping
+
 - name: "Include OS family specific variables."
   ansible.builtin.include_vars: "{{ ansible_os_family }}.yml"
   tags:
diff --git a/roles/agent/vars/main.yml b/roles/agent/vars/main.yml
index f6a712bf6..6211fb2a7 100644
--- a/roles/agent/vars/main.yml
+++ b/roles/agent/vars/main.yml
@@ -2,3 +2,11 @@
 checkmk_agent_site_url: "{{ checkmk_agent_protocol }}://{{ checkmk_agent_server }}:{{ checkmk_agent_port }}/{{ checkmk_agent_site }}"
 
 checkmk_agent_auth: "{% if checkmk_agent_secret is defined and checkmk_agent_secret | length %}{{ checkmk_agent_secret }}{% else %}{{ checkmk_agent_pass }}{% endif %}"   # noqa yaml[line-length]
+
+# Due to inconsistent naming of editions, we normalize them here for convenience
+checkmk_agent_edition_mapping:
+  cre: raw
+  cfe: free
+  cee: enterprise
+  cce: cloud
+  cme: managed