diff --git a/tasks/parse-version-windows.yml b/tasks/parse-version-windows.yml
index e562d9fc..cf307d3e 100644
--- a/tasks/parse-version-windows.yml
+++ b/tasks/parse-version-windows.yml
@@ -19,3 +19,20 @@
   failed_when: false
   check_mode: false
   when: ansible_facts.os_family == "Windows"
+
+- name: Parse installed Windows Agent version into components
+  ansible.builtin.set_fact:
+    agent_datadog_installed_version: "{{ agent_datadog_version_check_win.stdout | trim |
+      regex_search(installed_agent_regexp, '\\g<major>', '\\g<minor>', '\\g<bugfix>') }}"
+  vars:
+    installed_agent_regexp: (?P<major>[0-9]+)\.(?P<minor>[0-9]+)\.(?P<bugfix>[0-9]+)
+  when: >-
+    ansible_facts.os_family == "Windows" and
+    agent_datadog_version_check_win.stdout | trim | length > 0
+
+- name: Set installed version component vars
+  ansible.builtin.set_fact:
+    agent_datadog_installed_major: "{{ agent_datadog_installed_version.0 | default('', true) | string }}"
+    agent_datadog_installed_minor: "{{ agent_datadog_installed_version.1 | default('', true) | string }}"
+    agent_datadog_installed_bugfix: "{{ agent_datadog_installed_version.2 | default('', true) | string }}"
+  when: ansible_facts.os_family == "Windows" and agent_datadog_version_check_win.stdout | trim | length > 0
diff --git a/tasks/pkg-windows-opts.yml b/tasks/pkg-windows-opts.yml
index d5c39682..97ce38fb 100644
--- a/tasks/pkg-windows-opts.yml
+++ b/tasks/pkg-windows-opts.yml
@@ -125,3 +125,39 @@
   when: >-
     (agent_datadog_skip_install and (agent_datadog_major | int <= 7) and (agent_datadog_minor | int < 45)) and
     (("NPM" in agent_windows_active_features.stdout_lines) != agent_datadog_sysprobe_enabled)
+
+# Check if downgrade is requested (installed version is higher than requested version)
+- name: Initialize downgrade detection flag
+  ansible.builtin.set_fact:
+    agent_datadog_downgrade_detected: false
+
+- name: Detect if downgrade is requested
+  ansible.builtin.set_fact:
+    agent_datadog_downgrade_detected: true
+  when: >-
+    agent_datadog_installed_major is defined and
+    agent_datadog_installed_minor is defined and
+    agent_datadog_installed_bugfix is defined and
+    (
+      (agent_datadog_installed_major | int > agent_datadog_major | int) or
+      (agent_datadog_installed_major | int == agent_datadog_major | int and
+       agent_datadog_installed_minor | int > agent_datadog_minor | int) or
+      (agent_datadog_installed_major | int == agent_datadog_major | int and
+       agent_datadog_installed_minor | int == agent_datadog_minor | int and
+       agent_datadog_installed_bugfix | int > agent_datadog_bugfix | int)
+    )
+
+- name: Warn about downgrade
+  ansible.builtin.debug:
+    msg: >-
+      datadog_agent_version {{ agent_datadog_major }}.{{ agent_datadog_minor }}.{{ agent_datadog_bugfix }}
+      is lower than installed version
+      {{ agent_datadog_installed_major }}.{{ agent_datadog_installed_minor }}.{{ agent_datadog_installed_bugfix }},
+      proceeding to downgrade by uninstalling current version first
+  when: agent_datadog_downgrade_detected
+
+- name: Force reinstall for downgrade
+  ansible.builtin.set_fact:
+    agent_datadog_skip_install: false
+    agent_datadog_force_reinstall: true
+  when: agent_datadog_downgrade_detected