diff --git a/roles/agent/defaults/main.yml b/roles/agent/defaults/main.yml
index e6a6df6bc..aebaadc49 100644
--- a/roles/agent/defaults/main.yml
+++ b/roles/agent/defaults/main.yml
@@ -49,7 +49,7 @@ checkmk_agent_configure_firewall: true
 
 ## Delegation
 checkmk_agent_delegate_api_calls: 'localhost'
-checkmk_agent_delegate_download: "{{ inventory_hostname }}"
+checkmk_agent_delegate_download: true
 checkmk_agent_delegate_registration: false
 checkmk_agent_delegate_registration_target: "{{ inventory_hostname }}"
 
diff --git a/roles/agent/tasks/Debian.yml b/roles/agent/tasks/Debian.yml
index 12fc3d797..16d8db70c 100644
--- a/roles/agent/tasks/Debian.yml
+++ b/roles/agent/tasks/Debian.yml
@@ -2,7 +2,7 @@
 - name: "{{ ansible_facts['os_family'] }} Derivatives: Install host-specific {{ checkmk_agent_edition | upper }} Agent."
   become: true
   ansible.builtin.package:
-    deb: "{{ __checkmk_agent_agent.file.host }}"
+    deb: "{{ __checkmk_agent_agent.file.upload.host }}"
     force: "{{ checkmk_agent_force_install | bool }}"
     state: present
   when: |
@@ -14,7 +14,7 @@
 - name: "{{ ansible_facts['os_family'] }} Derivatives: Install folder-specific {{ checkmk_agent_edition | upper }} Agent."
   become: true
   ansible.builtin.package:
-    deb: "{{ __checkmk_agent_agent.file.pro }}"
+    deb: "{{ __checkmk_agent_agent.file.upload.pro }}"
     force: "{{ checkmk_agent_force_install | bool }}"
     state: present
   when: |
@@ -26,7 +26,7 @@
 - name: "{{ ansible_facts['os_family'] }} Derivatives: Install Vanilla Agent."
   become: true
   ansible.builtin.package:
-    deb: "{{ __checkmk_agent_agent.file.community }}"
+    deb: "{{ __checkmk_agent_agent.file.upload.community }}"
     force: "{{ checkmk_agent_force_install | bool }}"
     state: present
   when: |
diff --git a/roles/agent/tasks/Linux-files.yml b/roles/agent/tasks/Linux-files.yml
index dcf689e5b..2d83b0f3d 100644
--- a/roles/agent/tasks/Linux-files.yml
+++ b/roles/agent/tasks/Linux-files.yml
@@ -1,123 +1,245 @@
 ---
-- name: "{{ ansible_facts['system'] }}: Download host-specific {{ checkmk_agent_edition | upper }} Agent."
-  ansible.builtin.uri:
-    url:
-      "{{ __checkmk_agent_agent.url.pro }}?\
-      host_name={{ checkmk_agent_host_name }}&\
-      os_type={{ __checkmk_agent_files_mapping[ansible_facts['os_family']] }}&\
-      agent_type=host_name"
-    validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
-    dest: "{{ __checkmk_agent_agent.file.host }}"
-    method: GET
-    headers:
-      Authorization: "Bearer {{ checkmk_agent_user }} {{ __checkmk_agent_auth }}"
-      Accept: "application/octet-stream"
-    timeout: "{{ checkmk_agent_download_timeout | default(omit) }}"
-  when: |
-    checkmk_agent_edition | lower != "community"
-  become: false
-  register: __checkmk_agent_host_download_state
-  # This task may fail, as we fall back to the vanilla agent later
-  failed_when: false
-  changed_when: __checkmk_agent_host_download_state.status is defined and __checkmk_agent_host_download_state.status == 200
-  delegate_to: "{{ checkmk_agent_delegate_download }}"
-  tags:
-    - download-package
+- name: Copy block for Linux target and Linux controller
+  when: not __checkmk_agent_delegate_is_windows
+  block:
+    - name: "{{ ansible_facts['system'] }}: Download host-specific {{ checkmk_agent_edition | upper }} Agent."
+      ansible.builtin.uri:
+        url: "{{ __checkmk_agent_agent.url.pro }}?\
+          host_name={{ checkmk_agent_host_name }}&\
+          os_type={{ __checkmk_agent_files_mapping[ansible_facts['os_family']] }}&\
+          agent_type=host_name"
+        validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
+        dest: "{{ __checkmk_agent_agent.file.download.host }}"
+        method: GET
+        headers:
+          Authorization: "Bearer {{ checkmk_agent_user }} {{ __checkmk_agent_auth }}"
+          Accept: "application/octet-stream"
+        mode: "0644"
+        timeout: "{{ checkmk_agent_download_timeout | default(omit) }}"
+      when: |
+        checkmk_agent_edition | lower != "community"
+      become: false
+      register: __checkmk_agent_host_download_state
+      # This task may fail, as we fall back to the vanilla agent later
+      failed_when: false
+      changed_when: __checkmk_agent_host_download_state.status is defined and __checkmk_agent_host_download_state.status == 200
+      delegate_to: "{{ 'localhost' if checkmk_agent_delegate_download else 'inventory_hostname' }}"
+      tags:
+        - download-package
 
-- name: "Record host-specific agent download result."
-  ansible.builtin.set_fact:
-    checkmk_agent_host_specific: >-
-      {{ (__checkmk_agent_host_download_state.status is defined and __checkmk_agent_host_download_state.status == 200) | bool }}
-  tags:
-    - download-package
+    - name: "Record host-specific agent download result."
+      ansible.builtin.set_fact:
+        checkmk_agent_host_specific: >-
+          {{ (__checkmk_agent_host_download_state.status is defined and __checkmk_agent_host_download_state.status == 200) | bool }}
+      tags:
+        - download-package
 
-- name: "{{ ansible_facts['system'] }}: Download folder-specific {{ checkmk_agent_edition | upper }} Agent."
-  ansible.builtin.uri:
-    url:
-      "{{ __checkmk_agent_agent.url.pro }}?\
-      os_type={{ __checkmk_agent_files_mapping[ansible_facts['os_family']] }}&\
-      folder_name={{ checkmk_agent_folder }}&\
-      agent_type=generic"
-    validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
-    dest: "{{ __checkmk_agent_agent.file.pro }}"
-    method: GET
-    headers:
-      Authorization: "Bearer {{ checkmk_agent_user }} {{ __checkmk_agent_auth }}"
-      Accept: "application/octet-stream"
-    timeout: "{{ checkmk_agent_download_timeout | default(omit) }}"
-  become: false
-  register: __checkmk_agent_folder_download_state
-  when: |
-    checkmk_agent_edition | lower != "community"
-    and checkmk_agent_folder is defined
-    and not checkmk_agent_host_specific | bool
-  retries: 3
-  delay: 10
-  # This task may fail, as we fall back to the vanilla agent later
-  failed_when: false
-  changed_when: __checkmk_agent_folder_download_state.status is defined and __checkmk_agent_folder_download_state.status == 200
-  delegate_to: "{{ checkmk_agent_delegate_download }}"
-  tags:
-    - download-package
+    - name: "{{ ansible_facts['system'] }}: Download folder-specific {{ checkmk_agent_edition | upper }} Agent."
+      ansible.builtin.uri:
+        url: "{{ __checkmk_agent_agent.url.pro }}?\
+          os_type={{ __checkmk_agent_files_mapping[ansible_facts['os_family']] }}&\
+          folder_name={{ checkmk_agent_folder }}&\
+          agent_type=generic"
+        validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
+        dest: "{{ __checkmk_agent_agent.file.download.pro }}"
+        method: GET
+        headers:
+          Authorization: "Bearer {{ checkmk_agent_user }} {{ __checkmk_agent_auth }}"
+          Accept: "application/octet-stream"
+        mode: "0644"
+        timeout: "{{ checkmk_agent_download_timeout | default(omit) }}"
+      become: false
+      register: __checkmk_agent_folder_download_state
+      when: |
+        checkmk_agent_edition | lower != "community"
+        and checkmk_agent_folder is defined
+        and not checkmk_agent_host_specific | bool
+      retries: 3
+      delay: 10
+      # This task may fail, as we fall back to the vanilla agent later
+      failed_when: false
+      changed_when: __checkmk_agent_folder_download_state.status is defined and __checkmk_agent_folder_download_state.status == 200
+      delegate_to: "{{ 'localhost' if checkmk_agent_delegate_download else 'inventory_hostname' }}"
+      tags:
+        - download-package
 
-- name: "Record folder-specific agent download result."
-  ansible.builtin.set_fact:
-    checkmk_agent_folder_specific: >-
-      {{ (__checkmk_agent_folder_download_state.status is defined and __checkmk_agent_folder_download_state.status == 200) | bool }}
-  tags:
-    - download-package
+    - name: "Record folder-specific agent download result."
+      ansible.builtin.set_fact:
+        checkmk_agent_folder_specific: >-
+          {{ (__checkmk_agent_folder_download_state.status is defined and __checkmk_agent_folder_download_state.status == 200) | bool }}
+      tags:
+        - download-package
 
-- name: "{{ ansible_facts['system'] }}: Download Vanilla {{ checkmk_agent_edition | upper }} Agent."
-  ansible.builtin.get_url:  # This has to be the `get_url` module, as the download works different than for the bakery-based tasks.
-    url: "{{ __checkmk_agent_agent.url.community }}"
-    validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
-    dest: "{{ __checkmk_agent_agent.file.community }}"
-    mode: '0644'
-    timeout: "{{ checkmk_agent_download_timeout | default(omit) }}"
-  become: false
-  register: __checkmk_agent_vanilla_download_state
-  when: |
-    checkmk_agent_edition | lower == "community"
-    or not (checkmk_agent_host_specific | bool or checkmk_agent_folder_specific | bool)
-  retries: 3
-  delay: 10
-  until: "not __checkmk_agent_vanilla_download_state.failed | bool"
-  delegate_to: "{{ checkmk_agent_delegate_download }}"
-  tags:
-    - download-package
+    - name: "{{ ansible_facts['system'] }}: Download Vanilla {{ checkmk_agent_edition | upper }} Agent."
+      ansible.builtin.get_url: # This has to be the `get_url` module, as the download works different than for the bakery-based tasks.
+        url: "{{ __checkmk_agent_agent.url.community }}"
+        validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
+        dest: "{{ __checkmk_agent_agent.file.download.community }}"
+        mode: "0644"
+        timeout: "{{ checkmk_agent_download_timeout | default(omit) }}"
+      become: false
+      register: __checkmk_agent_vanilla_download_state
+      when: |
+        checkmk_agent_edition | lower == "community"
+        or not (checkmk_agent_host_specific | bool or checkmk_agent_folder_specific | bool)
+      retries: 3
+      delay: 10
+      until: "not __checkmk_agent_vanilla_download_state.failed | bool"
+      delegate_to: "{{ 'localhost' if checkmk_agent_delegate_download else 'inventory_hostname' }}"
+      tags:
+        - download-package
 
-- name: "{{ ansible_facts['system'] }}: 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 | lower != "community"
-    and checkmk_agent_host_specific | bool
-    and checkmk_agent_delegate_download != inventory_hostname
-  tags:
-    - download-package
+    - name: "{{ ansible_facts['system'] }}: Transfer host-specific {{ checkmk_agent_edition | upper }} Agent."
+      ansible.builtin.copy:
+        src: "{{ __checkmk_agent_agent.file.download.host }}"
+        dest: "{{ __checkmk_agent_agent.file.upload.host }}"
+        mode: "0644"
+      when: |
+        checkmk_agent_edition | lower != "community"
+        and checkmk_agent_host_specific | bool
+        and checkmk_agent_delegate_download != inventory_hostname
+      tags:
+        - download-package
 
-- name: "{{ ansible_facts['system'] }}: Transfer folder-specific {{ checkmk_agent_edition | upper }} Agent."
-  ansible.builtin.copy:
-    src: "{{ __checkmk_agent_agent.file.pro }}"
-    dest: "{{ __checkmk_agent_agent.file.pro }}"
-    mode: "0644"
-  when: |
-    checkmk_agent_edition | lower != "community"
-    and checkmk_agent_folder_specific | bool
-    and checkmk_agent_delegate_download != inventory_hostname
-  tags:
-    - download-package
+    - name: "{{ ansible_facts['system'] }}: Transfer folder-specific {{ checkmk_agent_edition | upper }} Agent."
+      ansible.builtin.copy:
+        src: "{{ __checkmk_agent_agent.file.download.pro }}"
+        dest: "{{ __checkmk_agent_agent.file.upload.pro }}"
+        mode: "0644"
+      when: |
+        checkmk_agent_edition | lower != "community"
+        and checkmk_agent_folder_specific | bool
+        and checkmk_agent_delegate_download != inventory_hostname
+      tags:
+        - download-package
 
-- name: "{{ ansible_facts['system'] }}: Transfer Vanilla {{ checkmk_agent_edition | upper }} Agent."
-  ansible.builtin.copy:
-    src: "{{ __checkmk_agent_agent.file.community }}"
-    dest: "{{ __checkmk_agent_agent.file.community }}"
-    mode: "0644"
-  when: |
-    checkmk_agent_delegate_download != inventory_hostname
-    and (checkmk_agent_edition | lower == "community"
-    or not (checkmk_agent_host_specific | bool or checkmk_agent_folder_specific | bool))
-  tags:
-    - download-package
+    - name: "{{ ansible_facts['system'] }}: Transfer Vanilla {{ checkmk_agent_edition | upper }} Agent."
+      ansible.builtin.copy:
+        src: "{{ __checkmk_agent_agent.file.download.community }}"
+        dest: "{{ __checkmk_agent_agent.file.upload.community }}"
+        mode: "0644"
+      when: |
+        checkmk_agent_delegate_download != inventory_hostname
+        and (checkmk_agent_edition | lower == "community"
+        or not (checkmk_agent_host_specific | bool or checkmk_agent_folder_specific | bool))
+      tags:
+        - download-package
+
+- name: Copy block for Windows target and Linux controller
+  when: __checkmk_agent_delegate_is_windows
+  block:
+    - name: "{{ ansible_facts['system'] }}: Download host-specific {{ checkmk_agent_edition | upper }} Agent."
+      ansible.windows.win_get_url:
+        url: "{{ __checkmk_agent_agent.url.pro }}?\
+          host_name={{ checkmk_agent_host_name }}&\
+          os_type={{ __checkmk_agent_files_mapping[ansible_facts['os_family']] }}&\
+          agent_type=host_name"
+        validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
+        dest: "{{ __checkmk_agent_agent.file.download.host }}"
+        method: GET
+        headers:
+          Authorization: "Bearer {{ checkmk_agent_user }} {{ __checkmk_agent_auth }}"
+          Accept: "application/octet-stream"
+        timeout: "{{ checkmk_agent_download_timeout | default(omit) }}"
+      when: |
+        checkmk_agent_edition | lower != "community"
+      become: false
+      register: __checkmk_agent_host_download_state
+      # This task may fail, as we fall back to the vanilla agent later
+      failed_when: false
+      changed_when: __checkmk_agent_host_download_state.status_code is defined and __checkmk_agent_host_download_state.status_code == 200
+      delegate_to: "{{ 'localhost' if checkmk_agent_delegate_download else 'inventory_hostname' }}"
+      tags:
+        - download-package
+
+    - name: "Record host-specific agent download result."
+      ansible.builtin.set_fact:
+        checkmk_agent_host_specific: >-
+          {{ (__checkmk_agent_host_download_state.status_code is defined and __checkmk_agent_host_download_state.status_code == 200) | bool }}
+      tags:
+        - download-package
+
+    - name: "{{ ansible_facts['system'] }}: Download folder-specific {{ checkmk_agent_edition | upper }} Agent."
+      ansible.windows.win_get_url:
+        url: "{{ __checkmk_agent_agent.url.pro }}?\
+          os_type={{ __checkmk_agent_files_mapping[ansible_facts['os_family']] }}&\
+          folder_name={{ checkmk_agent_folder }}&\
+          agent_type=generic"
+        validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
+        dest: "{{ __checkmk_agent_agent.file.download.pro }}"
+        method: GET
+        headers:
+          Authorization: "Bearer {{ checkmk_agent_user }} {{ __checkmk_agent_auth }}"
+          Accept: "application/octet-stream"
+        timeout: "{{ checkmk_agent_download_timeout | default(omit) }}"
+      become: false
+      register: __checkmk_agent_folder_download_state
+      when: |
+        checkmk_agent_edition | lower != "community"
+        and checkmk_agent_folder is defined
+        and not checkmk_agent_host_specific | bool
+      retries: 3
+      delay: 10
+      # This task may fail, as we fall back to the vanilla agent later
+      failed_when: false
+      changed_when: __checkmk_agent_folder_download_state.status_code is defined and __checkmk_agent_folder_download_state.status_code == 200
+      delegate_to: "{{ 'localhost' if checkmk_agent_delegate_download else 'inventory_hostname' }}"
+      tags:
+        - download-package
+
+    - name: "Record folder-specific agent download result."
+      ansible.builtin.set_fact:
+        checkmk_agent_folder_specific: >-
+          {{ (__checkmk_agent_folder_download_state.status_code is defined and __checkmk_agent_folder_download_state.status_code == 200) | bool }}
+      tags:
+        - download-package
+
+    - name: "{{ ansible_facts['system'] }}: Download Vanilla {{ checkmk_agent_edition | upper }} Agent."
+      ansible.windows.win_get_url:
+        url: "{{ __checkmk_agent_agent.url.community }}"
+        validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
+        dest: "{{ __checkmk_agent_agent.file.download.community }}"
+        timeout: "{{ checkmk_agent_download_timeout | default(omit) }}"
+      when: |
+        checkmk_agent_edition | lower == "community"
+        or not (checkmk_agent_host_specific | bool or checkmk_agent_folder_specific | bool)
+      register: __checkmk_agent_vanilla_download_state
+      retries: 3
+      delay: 10
+      until: "not __checkmk_agent_vanilla_download_state.failed | bool"
+      delegate_to: "{{ 'localhost' if checkmk_agent_delegate_download else 'inventory_hostname' }}"
+      tags:
+        - download-package
+
+    - name: "{{ ansible_facts['system'] }}: Transfer host-specific {{ checkmk_agent_edition | upper }} Agent."
+      ansible.windows.win_copy:
+        src: "{{ __checkmk_agent_agent.file.download.host }}"
+        dest: "{{ __checkmk_agent_agent.file.upload.host }}"
+      when: |
+        checkmk_agent_edition | lower != "community"
+        and checkmk_agent_host_specific | bool
+        and checkmk_agent_delegate_download != inventory_hostname
+      tags:
+        - download-package
+
+    - name: "{{ ansible_facts['system'] }}: Transfer folder-specific {{ checkmk_agent_edition | upper }} Agent."
+      ansible.windows.win_copy:
+        src: "{{ __checkmk_agent_agent.file.download.pro }}"
+        dest: "{{ __checkmk_agent_agent.file.upload.pro }}"
+      when: |
+        checkmk_agent_edition | lower != "community"
+        and checkmk_agent_folder_specific | bool
+        and checkmk_agent_delegate_download != inventory_hostname
+      tags:
+        - download-package
+
+    - name: "{{ ansible_facts['system'] }}: Transfer Vanilla {{ checkmk_agent_edition | upper }} Agent."
+      ansible.windows.win_copy:
+        src: "{{ __checkmk_agent_agent.file.download.community }}"
+        dest: "{{ __checkmk_agent_agent.file.upload.community }}"
+      when: |
+        checkmk_agent_delegate_download != inventory_hostname
+        and (checkmk_agent_edition | lower == "community"
+        or not (checkmk_agent_host_specific | bool or checkmk_agent_folder_specific | bool))
+      tags:
+        - download-package
diff --git a/roles/agent/tasks/Linux.yml b/roles/agent/tasks/Linux.yml
index 83dab09bf..93bf8b9c5 100644
--- a/roles/agent/tasks/Linux.yml
+++ b/roles/agent/tasks/Linux.yml
@@ -90,7 +90,7 @@
   tags:
     - manage-host
 
-- name: "Ensure registration readiness."  # noqa no-handler
+- name: "Ensure registration readiness." # noqa no-handler
   tags:
     - always
   block:
@@ -268,7 +268,7 @@
   tags:
     - register-agent
 
-- name: "{{ ansible_facts['system'] }}: Initial push of data for push agent."  # noqa no-changed-when
+- name: "{{ ansible_facts['system'] }}: Initial push of data for push agent." # noqa no-changed-when
   become: true
   ansible.builtin.command: cmk-agent-ctl push
   when: checkmk_agent_mode == 'push'
@@ -280,8 +280,8 @@
     path: "{{ item }}"
     state: absent
   loop:
-    - "{{ __checkmk_agent_agent.file.community }}"
-    - "{{ __checkmk_agent_agent.file.pro }}"
-    - "{{ __checkmk_agent_agent.file.host }}"
+    - "{{ __checkmk_agent_agent.file.upload.community }}"
+    - "{{ __checkmk_agent_agent.file.upload.pro }}"
+    - "{{ __checkmk_agent_agent.file.upload.host }}"
   tags:
     - download-package
diff --git a/roles/agent/tasks/RedHat.yml b/roles/agent/tasks/RedHat.yml
index 658b81651..ce1fa7ebb 100644
--- a/roles/agent/tasks/RedHat.yml
+++ b/roles/agent/tasks/RedHat.yml
@@ -2,7 +2,7 @@
 - name: "{{ ansible_facts['os_family'] }} Derivatives: Install host-specific {{ checkmk_agent_edition | upper }} Agent."
   become: true
   ansible.builtin.package:
-    name: "{{ __checkmk_agent_agent.file.host }}"
+    name: "{{ __checkmk_agent_agent.file.upload.host }}"
     state: present
     disable_gpg_check: true
   when: |
@@ -14,7 +14,7 @@
 - name: "{{ ansible_facts['os_family'] }} Derivatives: Install folder-specific {{ checkmk_agent_edition | upper }} Agent."
   become: true
   ansible.builtin.package:
-    name: "{{ __checkmk_agent_agent.file.pro }}"
+    name: "{{ __checkmk_agent_agent.file.upload.pro }}"
     state: present
     disable_gpg_check: true
   when: |
@@ -26,7 +26,7 @@
 - name: "{{ ansible_facts['os_family'] }} Derivatives: Install Vanilla Agent."
   become: true
   ansible.builtin.package:
-    name: "{{ __checkmk_agent_agent.file.community }}"
+    name: "{{ __checkmk_agent_agent.file.upload.community }}"
     state: present
     disable_gpg_check: true
   when: |
diff --git a/roles/agent/tasks/Suse.yml b/roles/agent/tasks/Suse.yml
index d46d85a82..6abc0e7d6 100644
--- a/roles/agent/tasks/Suse.yml
+++ b/roles/agent/tasks/Suse.yml
@@ -2,7 +2,7 @@
 - name: "{{ ansible_facts['os_family'] }} Derivatives: Install host-specific {{ checkmk_agent_edition | upper }} Agent."
   become: true
   community.general.zypper:
-    name: "{{ __checkmk_agent_agent.file.host }}"
+    name: "{{ __checkmk_agent_agent.file.upload.host }}"
     force: "{{ checkmk_agent_force_install | bool }}"
     state: present
     disable_gpg_check: true
@@ -15,7 +15,7 @@
 - name: "{{ ansible_facts['os_family'] }} Derivatives: Install folder-specific {{ checkmk_agent_edition | upper }} Agent."
   become: true
   community.general.zypper:
-    name: "{{ __checkmk_agent_agent.file.pro }}"
+    name: "{{ __checkmk_agent_agent.file.upload.pro }}"
     force: "{{ checkmk_agent_force_install | bool }}"
     state: present
     disable_gpg_check: true
@@ -28,7 +28,7 @@
 - name: "{{ ansible_facts['os_family'] }} Derivatives: Install Vanilla Agent."
   become: true
   community.general.zypper:
-    name: "{{ __checkmk_agent_agent.file.community }}"
+    name: "{{ __checkmk_agent_agent.file.upload.community }}"
     force: "{{ checkmk_agent_force_install | bool }}"
     state: present
     disable_gpg_check: true
diff --git a/roles/agent/tasks/Win32NT-files.yml b/roles/agent/tasks/Win32NT-files.yml
index 82453ee94..b1714aeff 100644
--- a/roles/agent/tasks/Win32NT-files.yml
+++ b/roles/agent/tasks/Win32NT-files.yml
@@ -7,7 +7,7 @@
       os_type={{ __checkmk_agent_files_mapping[ansible_facts['os_family']] }}&\
       agent_type=host_name"
     validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
-    dest: "{{ __checkmk_agent_agent.file.host }}"
+    dest: "{{ __checkmk_agent_agent.file.download.host }}"
     method: GET
     headers:
       Authorization: "Bearer {{ checkmk_agent_user }} {{ __checkmk_agent_auth }}"
@@ -20,7 +20,7 @@
   # This task may fail, as we fall back to the vanilla agent later
   failed_when: false
   changed_when: __checkmk_agent_host_download_state.status_code is defined and __checkmk_agent_host_download_state.status_code == 200
-  delegate_to: "{{ checkmk_agent_delegate_download }}"
+  delegate_to: "{{ 'localhost' if checkmk_agent_delegate_download else 'inventory_hostname' }}"
   tags:
     - download-package
 
@@ -39,7 +39,7 @@
       folder_name={{ checkmk_agent_folder }}&\
       agent_type=generic"
     validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
-    dest: "{{ __checkmk_agent_agent.file.pro }}"
+    dest: "{{ __checkmk_agent_agent.file.download.pro }}"
     method: GET
     headers:
       Authorization: "Bearer {{ checkmk_agent_user }} {{ __checkmk_agent_auth }}"
@@ -56,7 +56,7 @@
   # This task may fail, as we fall back to the vanilla agent later
   failed_when: false
   changed_when: __checkmk_agent_folder_download_state.status_code is defined and __checkmk_agent_folder_download_state.status_code == 200
-  delegate_to: "{{ checkmk_agent_delegate_download }}"
+  delegate_to: "{{ 'localhost' if checkmk_agent_delegate_download else 'inventory_hostname' }}"
   tags:
     - download-package
 
@@ -71,7 +71,7 @@
   ansible.windows.win_get_url:
     url: "{{ __checkmk_agent_agent.url.community }}"
     validate_certs: "{{ checkmk_agent_server_validate_certs | bool }}"
-    dest: "{{ __checkmk_agent_agent.file.community }}"
+    dest: "{{ __checkmk_agent_agent.file.download.community }}"
     timeout: "{{ checkmk_agent_download_timeout | default(omit) }}"
   when: |
     checkmk_agent_edition | lower == "community"
@@ -80,14 +80,14 @@
   retries: 3
   delay: 10
   until: "not __checkmk_agent_vanilla_download_state.failed | bool"
-  delegate_to: "{{ checkmk_agent_delegate_download }}"
+  delegate_to: "{{ 'localhost' if checkmk_agent_delegate_download else 'inventory_hostname' }}"
   tags:
     - download-package
 
 - name: "{{ ansible_facts['system'] }}: Transfer host-specific {{ checkmk_agent_edition | upper }} Agent."
   ansible.windows.win_copy:
-    src: "{{ __checkmk_agent_agent.file.host }}"
-    dest: "{{ __checkmk_agent_agent.file.host }}"
+    src: "{{ __checkmk_agent_agent.file.download.host }}"
+    dest: "{{ __checkmk_agent_agent.file.upload.host }}"
   when: |
     checkmk_agent_edition | lower != "community"
     and checkmk_agent_host_specific | bool
@@ -97,8 +97,8 @@
 
 - name: "{{ ansible_facts['system'] }}: Transfer folder-specific {{ checkmk_agent_edition | upper }} Agent."
   ansible.windows.win_copy:
-    src: "{{ __checkmk_agent_agent.file.pro }}"
-    dest: "{{ __checkmk_agent_agent.file.pro }}"
+    src: "{{ __checkmk_agent_agent.file.download.pro }}"
+    dest: "{{ __checkmk_agent_agent.file.upload.pro }}"
   when: |
     checkmk_agent_edition | lower != "community"
     and checkmk_agent_folder_specific | bool
@@ -108,8 +108,8 @@
 
 - name: "{{ ansible_facts['system'] }}: Transfer Vanilla {{ checkmk_agent_edition | upper }} Agent."
   ansible.windows.win_copy:
-    src: "{{ __checkmk_agent_agent.file.community }}"
-    dest: "{{ __checkmk_agent_agent.file.community }}"
+    src: "{{ __checkmk_agent_agent.file.download.community }}"
+    dest: "{{ __checkmk_agent_agent.file.upload.community }}"
   when: |
     checkmk_agent_delegate_download != inventory_hostname
     and (checkmk_agent_edition | lower == "community"
diff --git a/roles/agent/tasks/Windows.yml b/roles/agent/tasks/Windows.yml
index 28e0c91d1..b60c3e57b 100644
--- a/roles/agent/tasks/Windows.yml
+++ b/roles/agent/tasks/Windows.yml
@@ -1,7 +1,7 @@
 ---
 - name: "{{ ansible_facts['os_family'] }}: Install host-specific {{ checkmk_agent_edition | upper }} Agent."
   ansible.windows.win_package:
-    path: "{{ __checkmk_agent_agent.file.host }}"
+    path: "{{ __checkmk_agent_agent.file.upload.host }}"
     state: present
   when: |
     checkmk_agent_edition | lower != "community"
@@ -11,7 +11,7 @@
 
 - name: "{{ ansible_facts['os_family'] }}: Install folder-specific {{ checkmk_agent_edition | upper }} Agent."
   ansible.windows.win_package:
-    path: "{{ __checkmk_agent_agent.file.pro }}"
+    path: "{{ __checkmk_agent_agent.file.upload.pro }}"
     state: present
   when: |
     checkmk_agent_edition | lower != "community"
@@ -21,7 +21,7 @@
 
 - name: "{{ ansible_facts['os_family'] }}: Install Vanilla Agent."
   ansible.windows.win_package:
-    path: "{{ __checkmk_agent_agent.file.community }}"
+    path: "{{ __checkmk_agent_agent.file.upload.community }}"
     state: present
   when: |
     checkmk_agent_edition | lower == "community"
@@ -34,8 +34,8 @@
     path: "{{ item }}"
     state: absent
   loop:
-    - "{{ __checkmk_agent_agent.file.community }}"
-    - "{{ __checkmk_agent_agent.file.pro }}"
-    - "{{ __checkmk_agent_agent.file.host }}"
+    - "{{ __checkmk_agent_agent.file.upload.community }}"
+    - "{{ __checkmk_agent_agent.file.upload.pro }}"
+    - "{{ __checkmk_agent_agent.file.upload.host }}"
   tags:
     - download-package
diff --git a/roles/agent/tasks/main.yml b/roles/agent/tasks/main.yml
index 78e302ff2..ac9924e64 100644
--- a/roles/agent/tasks/main.yml
+++ b/roles/agent/tasks/main.yml
@@ -27,8 +27,30 @@
     - install-package
     - download-package
 
-- name: "{{ ansible_facts['system'] }}: Include agent package download tasks."
-  ansible.builtin.include_tasks: "{{ ansible_facts['system'] }}-files.yml"
+- name: "Preflight - Make sure facts for the delegate Host (Controller or Target Host) are present."
+  ansible.builtin.setup:
+  delegate_to: "{{ 'localhost' if checkmk_agent_delegate_download else inventory_hostname }}"
+  delegate_facts: true
+  tags:
+    - download-package
+
+- name: "Preflight - Set facts for the delegate Host (Controller or target Host)"
+  ansible.builtin.set_fact:
+    __checkmk_agent_delegate_is_windows: >-
+      {{ hostvars['localhost']['ansible_facts']['os_family'] == 'Windows' }}
+  tags:
+    - download-package
+
+- name: "{{ ansible_facts['system'] }}: Include agent package download tasks (Linux)."
+  ansible.builtin.include_tasks: "Linux-files.yml"
+  when: not __checkmk_agent_delegate_is_windows
+  tags:
+    - include-system-tasks
+    - download-package
+
+- name: "{{ ansible_facts['system'] }}: Include agent package download tasks (Windows)."
+  ansible.builtin.include_tasks: "Win32NT-files.yml"
+  when: __checkmk_agent_delegate_is_windows
   tags:
     - include-system-tasks
     - download-package
diff --git a/roles/agent/vars/Debian.yml b/roles/agent/vars/Debian.yml
index c1c1a55c8..2f2a49c24 100644
--- a/roles/agent/vars/Debian.yml
+++ b/roles/agent/vars/Debian.yml
@@ -1,11 +1,16 @@
 ---
-__checkmk_agent_host_tmp_dir: "/tmp"
+__checkmk_agent_lin_tmp_dir: "/tmp"
 
 __checkmk_agent_agent:
   url:
     community: "{{ __checkmk_agent_site_url }}/check_mk/agents/check-mk-agent_{{ checkmk_agent_version }}-1_all.deb"
     pro: "{{ __checkmk_agent_site_url }}/check_mk/api/1.0/domain-types/agent/actions/download_by_host/invoke"
   file:
-    community: "{{ __checkmk_agent_host_tmp_dir }}/check-mk-agent_{{ checkmk_agent_version }}-vanilla.deb"
-    pro: "{{ __checkmk_agent_host_tmp_dir }}/check-mk-agent_{{ checkmk_agent_version }}-generic.deb"
-    host: "{{ __checkmk_agent_host_tmp_dir }}/check-mk-agent_{{ checkmk_agent_version }}-{{ inventory_hostname }}.deb"
+    download:
+      community: "{{ __checkmk_agent_host_tmp_dir }}check-mk-agent_{{ checkmk_agent_version }}-vanilla.deb"
+      pro: "{{ __checkmk_agent_host_tmp_dir }}check-mk-agent_{{ checkmk_agent_version }}-generic.deb"
+      host: "{{ __checkmk_agent_host_tmp_dir }}check-mk-agent_{{ checkmk_agent_version }}-{{ inventory_hostname }}.deb"
+    upload:
+      community: "{{ __checkmk_agent_lin_tmp_dir }}/check-mk-agent_{{ checkmk_agent_version }}-vanilla.deb"
+      pro: "{{ __checkmk_agent_lin_tmp_dir }}/check-mk-agent_{{ checkmk_agent_version }}-generic.deb"
+      host: "{{ __checkmk_agent_lin_tmp_dir }}/check-mk-agent_{{ checkmk_agent_version }}-{{ inventory_hostname }}.deb"
diff --git a/roles/agent/vars/RedHat.yml b/roles/agent/vars/RedHat.yml
index cdd4a616e..b2b1a879d 100644
--- a/roles/agent/vars/RedHat.yml
+++ b/roles/agent/vars/RedHat.yml
@@ -1,11 +1,16 @@
 ---
-__checkmk_agent_host_tmp_dir: "/tmp"
+__checkmk_agent_lin_tmp_dir: "/tmp"
 
 __checkmk_agent_agent:
   url:
     community: "{{ __checkmk_agent_site_url }}/check_mk/agents/check-mk-agent-{{ checkmk_agent_version }}-1.noarch.rpm"
     pro: "{{ __checkmk_agent_site_url }}/check_mk/api/1.0/domain-types/agent/actions/download_by_host/invoke"
   file:
-    community: "{{ __checkmk_agent_host_tmp_dir }}/check-mk-agent-{{ checkmk_agent_version }}-1.noarch-vanilla.rpm"
-    pro: "{{ __checkmk_agent_host_tmp_dir }}/check-mk-agent-{{ checkmk_agent_version }}-1.noarch-generic.rpm"
-    host: "{{ __checkmk_agent_host_tmp_dir }}/check-mk-agent-{{ checkmk_agent_version }}-1.noarch-{{ inventory_hostname }}.rpm"
+    download:
+      community: "{{ __checkmk_agent_host_tmp_dir }}check-mk-agent-{{ checkmk_agent_version }}-1.noarch-vanilla.rpm"
+      pro: "{{ __checkmk_agent_host_tmp_dir }}check-mk-agent-{{ checkmk_agent_version }}-1.noarch-generic.rpm"
+      host: "{{ __checkmk_agent_host_tmp_dir }}check-mk-agent-{{ checkmk_agent_version }}-1.noarch-{{ inventory_hostname }}.rpm"
+    upload:
+      community: "{{ __checkmk_agent_host_tmp_dir }}/check-mk-agent-{{ checkmk_agent_version }}-1.noarch-vanilla.rpm"
+      pro: "{{ __checkmk_agent_host_tmp_dir }}/check-mk-agent-{{ checkmk_agent_version }}-1.noarch-generic.rpm"
+      host: "{{ __checkmk_agent_host_tmp_dir }}/check-mk-agent-{{ checkmk_agent_version }}-1.noarch-{{ inventory_hostname }}.rpm"
diff --git a/roles/agent/vars/Suse.yml b/roles/agent/vars/Suse.yml
index cdd4a616e..8431b70a8 100644
--- a/roles/agent/vars/Suse.yml
+++ b/roles/agent/vars/Suse.yml
@@ -1,11 +1,16 @@
 ---
-__checkmk_agent_host_tmp_dir: "/tmp"
+__checkmk_agent_lin_tmp_dir: "/tmp"
 
 __checkmk_agent_agent:
   url:
     community: "{{ __checkmk_agent_site_url }}/check_mk/agents/check-mk-agent-{{ checkmk_agent_version }}-1.noarch.rpm"
     pro: "{{ __checkmk_agent_site_url }}/check_mk/api/1.0/domain-types/agent/actions/download_by_host/invoke"
   file:
-    community: "{{ __checkmk_agent_host_tmp_dir }}/check-mk-agent-{{ checkmk_agent_version }}-1.noarch-vanilla.rpm"
-    pro: "{{ __checkmk_agent_host_tmp_dir }}/check-mk-agent-{{ checkmk_agent_version }}-1.noarch-generic.rpm"
-    host: "{{ __checkmk_agent_host_tmp_dir }}/check-mk-agent-{{ checkmk_agent_version }}-1.noarch-{{ inventory_hostname }}.rpm"
+    download:
+      community: "{{ __checkmk_agent_host_tmp_dir }}check-mk-agent-{{ checkmk_agent_version }}-1.noarch-vanilla.rpm"
+      pro: "{{ __checkmk_agent_host_tmp_dir }}check-mk-agent-{{ checkmk_agent_version }}-1.noarch-generic.rpm"
+      host: "{{ __checkmk_agent_host_tmp_dir }}check-mk-agent-{{ checkmk_agent_version }}-1.noarch-{{ inventory_hostname }}.rpm"
+    upload:
+      community: "{{ __checkmk_agent_lin_tmp_dir }}/check-mk-agent-{{ checkmk_agent_version }}-1.noarch-vanilla.rpm"
+      pro: "{{ __checkmk_agent_lin_tmp_dir }}/check-mk-agent-{{ checkmk_agent_version }}-1.noarch-generic.rpm"
+      host: "{{ __checkmk_agent_lin_tmp_dir }}/check-mk-agent-{{ checkmk_agent_version }}-1.noarch-{{ inventory_hostname }}.rpm"
diff --git a/roles/agent/vars/Windows.yml b/roles/agent/vars/Windows.yml
index 7a876e4ac..44552bcb4 100644
--- a/roles/agent/vars/Windows.yml
+++ b/roles/agent/vars/Windows.yml
@@ -1,5 +1,5 @@
 ---
-__checkmk_agent_host_tmp_dir: "C:\\Windows\\Temp"
+__checkmk_agent_win_tmp_dir: "C:\\Windows\\Temp"
 __checkmk_agent_controller_binary_path: "C:\\Program Files (x86)\\checkmk\\service\\cmk-agent-ctl.exe"
 __checkmk_agent_binary_path: "C:\\Program Files (x86)\\checkmk\\service\\check_mk_agent.exe"
 
@@ -8,6 +8,11 @@ __checkmk_agent_agent:
     community: "{{ __checkmk_agent_site_url }}/check_mk/agents/windows/check_mk_agent.msi"
     pro: "{{ __checkmk_agent_site_url }}/check_mk/api/1.0/domain-types/agent/actions/download_by_host/invoke"
   file:
-    community: "{{ __checkmk_agent_host_tmp_dir }}\\check-mk-agent_{{ checkmk_agent_version }}.msi"
-    pro: "{{ __checkmk_agent_host_tmp_dir }}\\check-mk-agent_{{ checkmk_agent_version }}.msi"
-    host: "{{ __checkmk_agent_host_tmp_dir }}\\check-mk-agent_{{ checkmk_agent_version }}-{{ inventory_hostname }}.msi"
+    download:
+      community: "{{ __checkmk_agent_host_tmp_dir }}check-mk-agent_{{ checkmk_agent_version }}.msi"
+      pro: "{{ __checkmk_agent_host_tmp_dir }}check-mk-agent_{{ checkmk_agent_version }}.msi"
+      host: "{{ __checkmk_agent_host_tmp_dir }}check-mk-agent_{{ checkmk_agent_version }}-{{ inventory_hostname }}.msi"
+    upload:
+      community: "{{ __checkmk_agent_win_tmp_dir }}\\check-mk-agent_{{ checkmk_agent_version }}.msi"
+      pro: "{{ __checkmk_agent_win_tmp_dir }}\\check-mk-agent_{{ checkmk_agent_version }}.msi"
+      host: "{{ __checkmk_agent_win_tmp_dir }}\\check-mk-agent_{{ checkmk_agent_version }}-{{ inventory_hostname }}.msi"
diff --git a/roles/agent/vars/main.yml b/roles/agent/vars/main.yml
index b5b50fb6b..e4f532467 100644
--- a/roles/agent/vars/main.yml
+++ b/roles/agent/vars/main.yml
@@ -37,3 +37,7 @@ __checkmk_agent_files_mapping:
   RedHat: linux_rpm
   Suse: linux_rpm
   Windows: windows_msi
+
+# Temporary directory to download the agent to (Win-Path if controller runs on Windows, Lin-Path if controller runs on Linux)
+# Hast to include the suffix directory delimiter (Win = \\, Lin = /)
+__checkmk_agent_host_tmp_dir: "/tmp/"
\ No newline at end of file