diff --git a/lib/ansible/executor/module_common.py b/lib/ansible/executor/module_common.py
index f67948ac7be..d23c95acda6 100644
--- a/lib/ansible/executor/module_common.py
+++ b/lib/ansible/executor/module_common.py
@@ -623,7 +623,13 @@ def _find_module_utils(module_name, b_module_data, module_path, module_args, tas
     elif b'from ansible.module_utils.' in b_module_data:
         module_style = 'new'
         module_substyle = 'python'
-    elif REPLACER_WINDOWS in b_module_data or re.search(b'#Requires \-Module', b_module_data, re.IGNORECASE):
+    elif REPLACER_WINDOWS in b_module_data:
+        module_style = 'new'
+        module_substyle = 'powershell'
+        b_module_data = b_module_data.replace(REPLACER_WINDOWS, b'#Requires -Module Ansible.ModuleUtils.Legacy')
+    elif re.search(b'#Requires \-Module', b_module_data, re.IGNORECASE) \
+            or re.search(b'#Requires \-Version', b_module_data, re.IGNORECASE)\
+            or re.search(b'#AnsibleRequires \-OSVersion', b_module_data, re.IGNORECASE):
         module_style = 'new'
         module_substyle = 'powershell'
     elif REPLACER_JSONARGS in b_module_data:
@@ -785,16 +791,37 @@ def _find_module_utils(module_name, b_module_data, module_path, module_args, tas
 
         lines = b_module_data.split(b'\n')
         module_names = set()
+        become_required = False
+        min_os_version = None
+        min_ps_version = None
 
         requires_module_list = re.compile(to_bytes(r'(?i)^#\s*requires\s+\-module(?:s?)\s*(Ansible\.ModuleUtils\..+)'))
+        requires_ps_version = re.compile(to_bytes('(?i)^#requires\s+\-version\s+([0-9]+(\.[0-9]+){0,3})$'))
+        requires_os_version = re.compile(to_bytes('(?i)^#ansiblerequires\s+\-osversion\s+([0-9]+(\.[0-9]+){0,3})$'))
+        requires_become = re.compile(to_bytes('(?i)^#ansiblerequires\s+\-become$'))
 
         for line in lines:
-            # legacy, equivalent to #Requires -Modules powershell
-            if REPLACER_WINDOWS in line:
-                module_names.add(b'Ansible.ModuleUtils.Legacy')
-            line_match = requires_module_list.match(line)
-            if line_match:
-                module_names.add(line_match.group(1))
+            module_util_line_match = requires_module_list.match(line)
+            if module_util_line_match:
+                module_names.add(module_util_line_match.group(1))
+
+            requires_ps_version_match = requires_ps_version.match(line)
+            if requires_ps_version_match:
+                min_ps_version = to_text(requires_ps_version_match.group(1))
+                # Powershell cannot cast a string of "1" to version, it must
+                # have at least the major.minor for it to work so we append 0
+                if requires_ps_version_match.group(2) is None:
+                    min_ps_version = "%s.0" % min_ps_version
+
+            requires_os_version_match = requires_os_version.match(line)
+            if requires_os_version_match:
+                min_os_version = to_text(requires_os_version_match.group(1))
+                if requires_os_version_match.group(2) is None:
+                    min_os_version = "%s.0" % min_os_version
+
+            requires_become_match = requires_become.match(line)
+            if requires_become_match:
+                become_required = True
 
         for m in set(module_names):
             m = to_text(m)
@@ -809,6 +836,14 @@ def _find_module_utils(module_name, b_module_data, module_path, module_args, tas
                 )
             )
 
+        exec_manifest['min_ps_version'] = min_ps_version
+        exec_manifest['min_os_version'] = min_os_version
+        if become_required and 'become' not in exec_manifest["actions"]:
+            exec_manifest["actions"].insert(0, 'become')
+            exec_manifest["become_user"] = "SYSTEM"
+            exec_manifest["become_password"] = None
+            exec_manifest["become"] = to_text(base64.b64encode(to_bytes(become_wrapper)))
+
         # FUTURE: smuggle this back as a dict instead of serializing here; the connection plugin may need to modify it
         module_json = json.dumps(exec_manifest)
 
diff --git a/lib/ansible/plugins/shell/powershell.py b/lib/ansible/plugins/shell/powershell.py
index 23b670080f3..ed9985845ea 100644
--- a/lib/ansible/plugins/shell/powershell.py
+++ b/lib/ansible/plugins/shell/powershell.py
@@ -71,6 +71,26 @@ end {
     # TODO: handle binary modules
     # TODO: handle persistence
 
+    $min_os_version = [version]$payload.min_os_version
+    if ($min_os_version -ne $null) {
+        $actual_os_version = [System.Environment]::OSVersion.Version
+        if ($actual_os_version -lt $min_os_version) {
+            $msg = "This module cannot run on this OS as it requires a minimum version of $min_os_version, actual was $actual_os_version"
+            Write-Output (ConvertTo-Json @{failed=$true;msg=$msg})
+            exit 1
+        }
+    }
+
+    $min_ps_version = [version]$payload.min_ps_version
+    if ($min_ps_version -ne $null) {
+        $actual_ps_version = $PSVersionTable.PSVersion
+        if ($actual_ps_version -lt $min_ps_version) {
+            $msg = "This module cannot run as it requires a minimum PowerShell version of $min_ps_version, actual was $actual_ps_version"
+            Write-Output (ConvertTo-Json @{failed=$true;msg=$msg})
+            exit 1
+        }
+    }
+
     $actions = $payload.actions
 
     # pop 0th action as entrypoint
diff --git a/test/integration/targets/win_exec_wrapper/aliases b/test/integration/targets/win_exec_wrapper/aliases
new file mode 100644
index 00000000000..c6d61981670
--- /dev/null
+++ b/test/integration/targets/win_exec_wrapper/aliases
@@ -0,0 +1 @@
+windows/ci/group3
diff --git a/test/integration/targets/win_exec_wrapper/library/test_all_options.ps1 b/test/integration/targets/win_exec_wrapper/library/test_all_options.ps1
new file mode 100644
index 00000000000..7c2c9c7b0d8
--- /dev/null
+++ b/test/integration/targets/win_exec_wrapper/library/test_all_options.ps1
@@ -0,0 +1,12 @@
+#!powershell
+
+#Requires -Module Ansible.ModuleUtils.Legacy
+#Requires -Module Ansible.ModuleUtils.SID
+#Requires -Version 3.0
+#AnsibleRequires -OSVersion 6
+#AnsibleRequires -Become
+
+$output = &whoami.exe
+$sid = Convert-ToSID -account_name $output.Trim()
+
+Exit-Json -obj @{ output = $sid; changed = $false }
diff --git a/test/integration/targets/win_exec_wrapper/library/test_invalid_requires.ps1 b/test/integration/targets/win_exec_wrapper/library/test_invalid_requires.ps1
new file mode 100644
index 00000000000..89727ef1a18
--- /dev/null
+++ b/test/integration/targets/win_exec_wrapper/library/test_invalid_requires.ps1
@@ -0,0 +1,9 @@
+#!powershell
+
+#Requires -Module Ansible.ModuleUtils.Legacy
+# Requires -Version 20
+# AnsibleRequires -OSVersion 20
+
+# requires statement must be straight after the original # with now space, this module won't fail
+
+Exit-Json -obj @{ output = "output"; changed = $false }
diff --git a/test/integration/targets/win_exec_wrapper/library/test_min_os_version.ps1 b/test/integration/targets/win_exec_wrapper/library/test_min_os_version.ps1
new file mode 100644
index 00000000000..39b1ded1606
--- /dev/null
+++ b/test/integration/targets/win_exec_wrapper/library/test_min_os_version.ps1
@@ -0,0 +1,8 @@
+#!powershell
+
+#Requires -Module Ansible.ModuleUtils.Legacy
+#AnsibleRequires -OSVersion 20.0
+
+# this shouldn't run as no Windows OS will meet the version of 20.0
+
+Exit-Json -obj @{ output = "output"; changed = $false }
diff --git a/test/integration/targets/win_exec_wrapper/library/test_min_ps_version.ps1 b/test/integration/targets/win_exec_wrapper/library/test_min_ps_version.ps1
new file mode 100644
index 00000000000..bb5fd0f2a57
--- /dev/null
+++ b/test/integration/targets/win_exec_wrapper/library/test_min_ps_version.ps1
@@ -0,0 +1,8 @@
+#!powershell
+
+#Requires -Module Ansible.ModuleUtils.Legacy
+#Requires -Version 20.0.0.0
+
+# this shouldn't run as no PS Version will be at 20 in the near future
+
+Exit-Json -obj @{ output = "output"; changed = $false }
diff --git a/test/integration/targets/win_exec_wrapper/tasks/main.yml b/test/integration/targets/win_exec_wrapper/tasks/main.yml
new file mode 100644
index 00000000000..d082d56325c
--- /dev/null
+++ b/test/integration/targets/win_exec_wrapper/tasks/main.yml
@@ -0,0 +1,103 @@
+---
+- name: test out invalid options
+  test_invalid_requires:
+  register: invalid_options
+
+- name: assert test out invalid options
+  assert:
+    that:
+    - invalid_options|success
+    - invalid_options.output == "output"
+
+- name: test out invalid os version
+  test_min_os_version:
+  register: invalid_os_version
+  ignore_errors: yes
+
+- name: assert test out invalid os version
+  assert:
+    that:
+    - invalid_os_version|failed
+    - '"This module cannot run on this OS as it requires a minimum version of 20.0, actual was " in invalid_os_version.msg'
+
+- name: test out invalid powershell version
+  test_min_ps_version:
+  register: invalid_ps_version
+  ignore_errors: yes
+
+- name: assert test out invalid powershell version
+  assert:
+    that:
+    - invalid_ps_version|failed
+    - '"This module cannot run as it requires a minimum PowerShell version of 20.0.0.0, actual was " in invalid_ps_version.msg'
+
+- name: test out become requires without become_user set
+  test_all_options:
+  register: become_system
+
+- name: assert become requires without become_user set
+  assert:
+    that:
+    - become_system|success
+    - become_system.output == "S-1-5-18"
+
+- set_fact:
+    become_test_username: ansible_become_test
+    gen_pw: password123! + {{ lookup('password', '/dev/null chars=ascii_letters,digits length=8') }}
+
+- name: create unprivileged user
+  win_user:
+    name: "{{ become_test_username }}"
+    password: "{{ gen_pw }}"
+    update_password: always
+    groups: Users
+  register: become_test_user_result
+
+- name: execute tests and ensure that test user is deleted regardless of success/failure
+  block:
+  - name: ensure current user is not the become user
+    win_shell: whoami
+    register: whoami_out
+
+  - name: verify output
+    assert:
+      that:
+      - not whoami_out.stdout_lines[0].endswith(become_test_username)
+
+  - name: get become user profile dir so we can clean it up later
+    vars: &become_vars
+      ansible_become_user: "{{ become_test_username }}"
+      ansible_become_password: "{{ gen_pw }}"
+      ansible_become_method: runas
+      ansible_become: yes
+    win_shell: $env:USERPROFILE
+    register: profile_dir_out
+
+  - name: ensure profile dir contains test username (eg, if become fails silently, prevent deletion of real user profile)
+    assert:
+      that:
+      - become_test_username in profile_dir_out.stdout_lines[0]
+
+  - name: test out become requires when become_user set
+    test_all_options:
+    vars: *become_vars
+    register: become_system
+
+  - name: assert become requires when become_user set
+    assert:
+      that:
+      - become_system|success
+      - become_system.output == become_test_user_result.sid
+
+  always:
+  - name: ensure test user is deleted
+    win_user:
+      name: "{{ become_test_username }}"
+      state: absent
+
+  - name: ensure test user profile is deleted
+    # NB: have to work around powershell limitation of long filenames until win_file fixes it
+    win_shell: rmdir /S /Q {{ profile_dir_out.stdout_lines[0] }}
+    args:
+      executable: cmd.exe
+    when: become_test_username in profile_dir_out.stdout_lines[0]