diff --git a/lib/ansible/modules/windows/win_wait_for.ps1 b/lib/ansible/modules/windows/win_wait_for.ps1
new file mode 100644
index 00000000000..068736c5828
--- /dev/null
+++ b/lib/ansible/modules/windows/win_wait_for.ps1
@@ -0,0 +1,269 @@
+#!powershell
+# This file is part of Ansible
+
+# Copyright (c) 2017 Ansible Project
+# GNU General Public License v3.0+ (see COPYING or https://www.gnu.org/licenses/gpl-3.0.txt)
+
+#Requires -Module Ansible.ModuleUtils.Legacy.psm1
+
+$ErrorActionPreference = "Stop"
+
+$params = Parse-Args -arguments $args -supports_check_mode $true
+
+$connect_timeout = Get-AnsibleParam -obj $params -name "connect_timeout" -type "int" -default 5
+$delay = Get-AnsibleParam -obj $params -name "delay" -type "int"
+$exclude_hosts = Get-AnsibleParam -obj $params -name "exclude_hosts" -type "list"
+$hostname = Get-AnsibleParam -obj $params -name "host" -type "str" -default "127.0.0.1"
+$path = Get-AnsibleParam -obj $params -name "path" -type "path"
+$port = Get-AnsibleParam -obj $params -name "port" -type "int"
+$search_regex = Get-AnsibleParam -obj $params -name "search_regex" -type "string"
+$sleep = Get-AnsibleParam -obj $params -name "sleep" -type "int" -default 1
+$state = Get-AnsibleParam -obj $params -name "state" -type "str" -default "started" -validateset "present","started","stopped","absent","drained"
+$timeout = Get-AnsibleParam -obj $params -name "timeout" -type "int" -default 300
+
+$result = @{
+    changed = $false
+}
+
+# validate the input with the various options
+if ($port -ne $null -and $path -ne $null) {
+    Fail-Json $result "port and path parameter can not both be passed to win_wait_for"
+}
+if ($exclude_hosts -ne $null -and $state -ne "drained") {
+    Fail-Json $result "exclude_hosts should only be with state=drained"
+}
+if ($path -ne $null) {
+    if ($state -in @("stopped","drained")) {
+        Fail-Json $result "state=$state should only be used for checking a port in the win_wait_for module"
+    }
+    
+    if ($exclude_hosts -ne $null) {
+        Fail-Json $result "exclude_hosts should only be used when checking a port and state=drained in the win_wait_for module"
+    }
+}
+
+if ($port -ne $null) {
+    if ($search_regex -ne $null) {
+        Fail-Json $result "search_regex should by used when checking a string in a file in the win_wait_for module"
+    }
+
+    if ($exclude_hosts -ne $null -and $state -ne "drained") {
+        Fail-Json $result "exclude_hosts should be used when state=drained in the win_wait_for module"
+    }
+}
+
+Function Test-Port($hostname, $port) {
+    # try and resolve the IP/Host, if it fails then just use the host passed in
+    try {
+        $resolve_hostname = ([System.Net.Dns]::GetHostEntry($hostname)).HostName
+    } catch {
+        # oh well just use the IP addres
+        $resolve_hostname = $hostname
+    }
+
+    $timeout = $connect_timeout * 1000
+    $socket = New-Object -TypeName System.Net.Sockets.TcpClient
+    $connect = $socket.BeginConnect($resolve_hostname, $port, $null, $null)
+    $wait = $connect.AsyncWaitHandle.WaitOne($timeout, $false)
+
+    if ($wait) {
+        try {
+            $socket.EndConnect($connect) | Out-Null
+            $valid = $true
+        } catch {
+            $valid = $false
+        }
+    } else {
+        $valid = $false
+    }
+
+    $socket.Close()
+    $socket.Dispose()
+
+    $valid
+}
+
+Function Get-PortConnections($hostname, $port) {
+    $connections = @()
+
+    $conn_info = [Net.NetworkInformation.IPGlobalProperties]::GetIPGlobalProperties()
+    if ($hostname -eq "0.0.0.0") {
+        $active_connections = $conn_info.GetActiveTcpConnections() | Where-Object { $_.LocalEndPoint.Port -eq $port }
+    } else {
+        $active_connections = $conn_info.GetActiveTcpConnections() | Where-Object { $_.LocalEndPoint.Address -eq $hostname -and $_.LocalEndPoint.Port -eq $port }
+    }
+    
+    if ($active_connections -ne $null) {
+        foreach ($active_connection in $active_connections) {
+            $connections += $active_connection.RemoteEndPoint.Address
+        }
+    }
+
+    $connections
+}
+
+$module_start = Get-Date
+
+if ($delay -ne $null) {
+    Start-Sleep -Seconds $delay
+}
+
+$attempts = 0
+if ($path -eq $null -and $port -eq $null -and $state -eq "drained") {
+    Start-Sleep -Seconds $timeout
+} elseif ($path -ne $null) {
+    if ($state -in @("present", "started")) {
+        # check if the file exists or string exists in file
+        $start_time = Get-Date
+        $complete = $false
+        while (((Get-Date) - $start_time).TotalSeconds -lt $timeout) {
+            $attempts += 1
+            if (Test-Path -Path $path) {
+                if ($search_regex -eq $null) {
+                    $complete = $true
+                    break
+                } else {
+                    $file_contents = Get-Content -Path $path -Raw
+                    if ($file_contents -match $search_regex) {
+                        $complete = $true
+                        break
+                    }
+                }
+            }
+            Start-Sleep -Seconds $sleep
+        }
+
+        if ($complete -eq $false) {
+            $elapsed_seconds = ((Get-Date) - $module_start).TotalSeconds
+            $result.attempts = $attempts
+            $result.elapsed = $elapsed_seconds
+            if ($search_regex -eq $null) {
+                Fail-Json $result "timeout while waiting for file $path to be present"
+            } else {
+                Fail-Json $result "timeout while waiting for string regex $search_regex in file $path to match"
+            }  
+        }
+    } elseif ($state -in @("absent")) {
+        # check if the file is deleted or string doesn't exist in file
+        $start_time = Get-Date
+        $complete = $false
+        while (((Get-Date) - $start_time).TotalSeconds -lt $timeout) {
+            $attempts += 1
+            if (Test-Path -Path $path) {
+                if ($search_regex -ne $null) {
+                    $file_contents = Get-Content -Path $path -Raw
+                    if ($file_contents -notmatch $search_regex) {
+                        $complete = $true
+                        break
+                    }
+                }
+            } else {
+                $complete = $true
+                break
+            }
+
+            Start-Sleep -Seconds $sleep
+        }
+
+        if ($complete -eq $false) {
+            $elapsed_seconds = ((Get-Date) - $module_start).TotalSeconds
+            $result.attempts = $attempts
+            $result.elapsed = $elapsed_seconds
+            if ($search_regex -eq $null) {
+                Fail-Json $result "timeout while waiting for file $path to be absent"
+            } else {
+                Fail-Json $result "timeout while waiting for string regex $search_regex in file $path to not match"
+            }            
+        }
+    }
+} elseif ($port -ne $null) {
+    if ($state -in @("started","present")) {
+        # check that the port is online and is listening
+        $start_time = Get-Date
+        $complete = $false
+        while (((Get-Date) - $start_time).TotalSeconds -lt $timeout) {
+            $attempts += 1
+            $port_result = Test-Port -hostname $hostname -port $port
+            if ($port_result -eq $true) {
+                $complete = $true
+                break
+            }
+
+            Start-Sleep -Seconds $sleep
+        }
+
+        if ($complete -eq $false) {
+            $elapsed_seconds = ((Get-Date) - $module_start).TotalSeconds
+            $result.attempts = $attempts
+            $result.elapsed = $elapsed_seconds
+            Fail-Json $result "timeout while waiting for $($hostname):$port to start listening"
+        }
+    } elseif ($state -in @("stopped","absent")) {
+        # check that the port is offline and is not listening
+        $start_time = Get-Date
+        $complete = $false
+        while (((Get-Date) - $start_time).TotalSeconds -lt $timeout) {
+            $attempts += 1
+            $port_result = Test-Port -hostname $hostname -port $port
+            if ($port_result -eq $false) {
+                $complete = $true
+                break
+            }
+
+            Start-Sleep -Seconds $sleep
+        }
+
+        if ($complete -eq $false) {
+            $elapsed_seconds = ((Get-Date) - $module_start).TotalSeconds
+            $result.attempts = $attempts
+            $result.elapsed = $elapsed_seconds
+            Fail-Json $result "timeout while waiting for $($hostname):$port to stop listening"
+        }
+    } elseif ($state -eq "drained") {
+        # check that the local port is online but has no active connections
+        $start_time = Get-Date
+        $complete = $false
+        while (((Get-Date) - $start_time).TotalSeconds -lt $timeout) {
+            $attempts += 1
+            $active_connections = Get-PortConnections -hostname $hostname -port $port
+            if ($active_connections -eq $null) {
+                $complete = $true
+                break
+            } elseif ($active_connections.Count -eq 0) {
+                # no connections on port
+                $complete = $true
+                break
+            } else {
+                # there are listeners, check if we should ignore any hosts
+                if ($exclude_hosts -ne $null) {
+                    $connection_info = $active_connections
+                    foreach ($exclude_host in $exclude_hosts) {
+                        try {
+                            $exclude_ips = [System.Net.Dns]::GetHostAddresses($exclude_host) | ForEach-Object { Write-Output $_.IPAddressToString }
+                            $connection_info = $connection_info | Where-Object { $_ -notin $exclude_ips }
+                        } catch {} # ignore invalid hostnames
+                    }
+
+                    if ($connection_info.Count -eq 0) {
+                        $complete = $true
+                        break
+                    }
+                }
+            }
+
+            Start-Sleep -Seconds $sleep
+        }
+
+        if ($complete -eq $false) {
+            $elapsed_seconds = ((Get-Date) - $module_start).TotalSeconds
+            $result.attempts = $attempts
+            $result.elapsed = $elapsed_seconds
+            Fail-Json $result "timeout while waiting for $($hostname):$port to drain"
+        }
+    }  
+}
+
+$result.attempts = $attempts
+$result.elapsed = ((Get-Date) - $module_start).TotalSeconds
+
+Exit-Json $result
diff --git a/lib/ansible/modules/windows/win_wait_for.py b/lib/ansible/modules/windows/win_wait_for.py
new file mode 100644
index 00000000000..b3313db642a
--- /dev/null
+++ b/lib/ansible/modules/windows/win_wait_for.py
@@ -0,0 +1,142 @@
+#!/usr/bin/python
+# This file is part of Ansible
+
+# Copyright (c) 2017 Ansible Project
+# GNU General Public License v3.0+ (see COPYING or https://www.gnu.org/licenses/gpl-3.0.txt)
+
+# this is a windows documentation stub, actual code lives in the .ps1
+# file of the same name
+
+ANSIBLE_METADATA = {'metadata_version': '1.1',
+                    'status': ['preview'],
+                    'supported_by': 'community'}
+
+
+DOCUMENTATION = r'''
+---
+module: win_wait_for
+version_added: '2.4'
+short_description: Waits for a condition before continuing
+description:
+- You can wait for a set amount of time C(timeout), this is the default if
+  nothing is specified.
+- Waiting for a port to become available is useful for when services are not
+  immediately available after their init scripts return which is true of
+  certain Java application servers.
+- You can wait for a file to exist or not exist on the filesystem.
+- This module can also be used to wait for a regex match string to be present
+  in a file.
+- You can wait for active connections to be closed before continuing on a
+  local port.
+options:
+  connect_timeout:
+    description:
+    - The maximum number of seconds to wait for a connection to happen before
+      closing and retrying.
+    default: 5
+  delay:
+    description:
+    - The number of seconds to wait before starting to poll.
+  exclude_hosts:
+    description:
+    - The list of hosts or IPs to ignore when looking for active TCP
+      connections when C(state=drained).
+  host:
+    description:
+    - A resolvable hostname or IP address to wait for.
+    - If C(state=drained) then it will only check for connections on the IP
+      specified, you can use '0.0.0.0' to use all host IPs.
+    default: '127.0.0.1'
+  path:
+    description:
+    - The path to a file on the filesystem to check.
+    - If C(state) is present or started then it will wait until the file
+      exists.
+    - If C(state) is absent then it will wait until the file does not exist.
+  port:
+    description:
+    - The port number to poll on C(host).
+  search_regex:
+    description:
+    - Can be used to match a string in a file.
+    - If C(state) is present or started then it will wait until the regex
+      matches.
+    - If C(state) is absent then it will wait until the regex does not match.
+    - Defaults to a multiline regex.
+  sleep:
+    description:
+    - Number of seconds to sleep between checks.
+    default: 1
+  state:
+    description:
+    - When checking a port, C(started) will ensure the port is open, C(stopped)
+      will check that is it closed and C(drained) will check for active
+      connections.
+    - When checking for a file or a search string C(present) or C(started) will
+      ensure that the file or string is present, C(absent) will check that the
+      file or search string is absent or removed.
+    default: started
+    choices: [ present, started, stopped, absent, drained ]
+  timeout:
+    description:
+    - The maximum number of seconds to wait for.
+    default: 300
+author:
+- Jordan Borean (@jborean93)
+'''
+
+EXAMPLES = r'''
+- name: wait 300 seconds for port 8000 to become open on the host, don't start checking for 10 seconds
+  win_wait_for:
+    port: 8000
+    delay: 10
+
+- name: wait 150 seconds for port 8000 of any IP to close active connections
+  win_wait_for:
+    host: 0.0.0.0
+    port: 8000
+    state: drained
+    timeout: 150
+
+- name: wait for port 8000 of any IP to close active connection, ignoring certain hosts
+  win_wait_for:
+    host: 0.0.0.0
+    port: 8000
+    state: drained
+    exclude_hosts: ['10.2.1.2', '10.2.1.3']
+
+- name: wait for file C:\temp\log.txt to exist before continuing
+  win_wait_for:
+    path: C:\temp\log.txt
+
+- name: wait until process complete is in the file before continuing
+  win_wait_for:
+    path: C:\temp\log.txt
+    search_regex: process complete
+
+- name: wait until file if removed
+  win_wait_for:
+    path: C:\temp\log.txt
+    state: absent
+
+- name: wait until port 1234 is offline but try every 10 seconds
+  win_wait_for:
+    port: 1234
+    state: absent
+    sleep: 10
+'''
+
+RETURN = r'''
+attempts:
+  description: The number of attempts to poll the file or port before module
+    finishes.
+  returned: always
+  type: int
+  sample: 1
+elapsed:
+  description: The elapsed seconds between the start of poll and the end of the
+    module. This includes the delay if the option is set.
+  returned: always
+  type: float
+  sample: 2.1406487
+'''
diff --git a/test/integration/targets/win_wait_for/aliases b/test/integration/targets/win_wait_for/aliases
new file mode 100644
index 00000000000..e69de29bb2d
diff --git a/test/integration/targets/win_wait_for/defaults/main.yml b/test/integration/targets/win_wait_for/defaults/main.yml
new file mode 100644
index 00000000000..9e1155e3291
--- /dev/null
+++ b/test/integration/targets/win_wait_for/defaults/main.yml
@@ -0,0 +1,2 @@
+test_win_wait_for_path: C:\ansible\win_wait_for
+test_win_wait_for_port: 1234
diff --git a/test/integration/targets/win_wait_for/tasks/main.yml b/test/integration/targets/win_wait_for/tasks/main.yml
new file mode 100644
index 00000000000..a6272805d02
--- /dev/null
+++ b/test/integration/targets/win_wait_for/tasks/main.yml
@@ -0,0 +1,316 @@
+---
+- name: ensure test folder is deleted for clean slate
+  win_file:
+    path: '{{test_win_wait_for_path}}'
+    state: absent
+
+- name: ensure test folder exists
+  win_file:
+    path: '{{test_win_wait_for_path}}'
+    state: directory
+
+- name: template out the test server
+  win_template:
+    src: http-server.ps1
+    dest: '{{test_win_wait_for_path}}\http-server.ps1'
+
+# invalid arguments
+- name: fail to set port and path
+  win_wait_for:
+    path: a
+    port: 0
+  register: fail_port_and_path
+  failed_when: fail_port_and_path.msg != 'port and path parameter can not both be passed to win_wait_for'
+
+- name: fail to set exclude_hosts when state isn't drain
+  win_wait_for:
+    port: 0
+    exclude_hosts: a
+    state: present
+  register: fail_exclude_hosts_not_drained
+  failed_when: fail_exclude_hosts_not_drained.msg != 'exclude_hosts should only be with state=drained'
+
+- name: fail to set state drained with path
+  win_wait_for:
+    path: a
+    state: drained
+  register: fail_path_drained
+  failed_when: fail_path_drained.msg != 'state=drained should only be used for checking a port in the win_wait_for module'
+
+- name: fail to set exclude_hosts with path
+  win_wait_for:
+    path: a
+    exclude_hosts: a
+  register: fail_path_exclude_hosts
+  failed_when: fail_path_exclude_hosts.msg != 'exclude_hosts should only be with state=drained'
+
+- name: fail to set search_regex with port
+  win_wait_for:
+    port: 0
+    search_regex: a
+  register: fail_port_search_regex
+  failed_when: fail_port_search_regex.msg != 'search_regex should by used when checking a string in a file in the win_wait_for module'
+
+- name: fail to set exclude_hosts with port whens tate is not drained
+  win_wait_for:
+    port: 0
+    exclude_hosts: a
+    state: present
+  register: fail_port_exclude_hosts_not_drained
+  failed_when: fail_port_exclude_hosts_not_drained.msg != 'exclude_hosts should only be with state=drained'
+
+# path tests
+- name: timeout while waiting for file
+  win_wait_for:
+    path: '{{test_win_wait_for_path}}\test.txt'
+    state: present
+    timeout: 5
+  register: fail_timeout_file_present
+  ignore_errors: True
+
+- name: assert timeout while waiting for file
+  assert:
+    that:
+    - fail_timeout_file_present.msg == 'timeout while waiting for file ' + test_win_wait_for_path + '\\test.txt to be present'
+    - fail_timeout_file_present.attempts == 5
+    - fail_timeout_file_present.elapsed > 5
+
+- name: wait for file to not exist - non existing file
+  win_wait_for:
+    path: '{{test_win_wait_for_path}}\test.txt'
+    state: absent
+  register: wait_remove_no_file
+
+- name: assert wait for file to not exist - non existing file
+  assert:
+    that:
+    - wait_remove_no_file.attempts == 1
+
+- name: create file for next test
+  win_file:
+    path: '{{test_win_wait_for_path}}\test.txt'
+    state: touch
+
+- name: run async task to remove file after a timeout
+  win_shell: Start-Sleep -Seconds 5; Remove-Item -Path '{{test_win_wait_for_path}}\test.txt' -Force
+  async: 30
+  poll: 0
+
+- name: wait for file to not exist - existing file
+  win_wait_for:
+    path: '{{test_win_wait_for_path}}\test.txt'
+    state: absent
+  register: wait_remove_existing_file
+
+- name: assert wait for file to not exist - existing file
+  assert:
+    that:
+    - wait_remove_existing_file.attempts > 1
+
+- name: run async task to create file after a timeout
+  win_shell: Start-Sleep -Seconds 5; New-Item -Path '{{test_win_wait_for_path}}\test.txt' -Type File
+  async: 30
+  poll: 0
+
+- name: wait for file to exist - non existing file
+  win_wait_for:
+    path: '{{test_win_wait_for_path}}\test.txt'
+    state: present
+  register: wait_new_missing_file
+
+- name: assert wait for file to exist - non existing file
+  assert:
+    that:
+    - wait_new_missing_file.attempts > 1
+
+- name: wait for file to exist - existing file
+  win_wait_for:
+    path: '{{test_win_wait_for_path}}\test.txt'
+    state: present
+  register: wait_new_existing_file
+
+- name: assert wait for file to exist - existing file
+  assert:
+    that:
+    - wait_new_existing_file.attempts == 1
+
+- name: timeout while waiting for file to not exist
+  win_wait_for:
+    path: '{{test_win_wait_for_path}}\test.txt'
+    state: absent
+    timeout: 5
+  register: fail_timeout_file_absent
+  ignore_errors: True
+
+- name: assert timeout while waiting for file to not exist
+  assert:
+    that:
+    - fail_timeout_file_absent.msg == 'timeout while waiting for file ' + test_win_wait_for_path + '\\test.txt to be absent'
+    - fail_timeout_file_absent.attempts == 5
+    - fail_timeout_file_absent.elapsed > 5
+
+- name: run async task to populate file contents
+  win_shell: Start-Sleep -Seconds 5; Set-Content -Path '{{test_win_wait_for_path}}\test.txt' -Value 'hello world`r`nfile contents`r`nEnd line'
+  async: 30
+  poll: 0
+
+- name: wait for file contents to match regex - empty file
+  win_wait_for:
+    path: '{{test_win_wait_for_path}}\test.txt'
+    state: present
+    search_regex: file c.*
+  register: wait_regex_match_new
+
+- name: assert wait for file contents to match regex - empty file
+  assert:
+    that:
+    - wait_regex_match_new.attempts > 1
+
+- name: wait for file contents to match regex - existing file
+  win_wait_for:
+    path: '{{test_win_wait_for_path}}\test.txt'
+    state: present
+    search_regex: file c.*
+  register: wait_regex_match_existing
+
+- name: assert wait for file contents to match regex - existing file
+  assert:
+    that:
+    - wait_regex_match_existing.attempts == 1
+
+- name: run async task to clear file contents
+  win_shell: Start-Sleep -Seconds 5; Set-Content -Path '{{test_win_wait_for_path}}\test.txt' -Value 'hello world`r`nother contents for file`r`nEnd line'
+  async: 30
+  poll: 0
+
+- name: wait for file content to not match regex
+  win_wait_for:
+    path: '{{test_win_wait_for_path}}\test.txt'
+    state: absent
+    search_regex: file c.*
+  register: wait_regex_match_absent_remove
+
+- name: assert wait for file content to not match regex
+  assert:
+    that:
+    - wait_regex_match_absent_remove.attempts > 1
+
+- name: wait for file content to not match regex - existing
+  win_wait_for:
+    path: '{{test_win_wait_for_path}}\test.txt'
+    state: absent
+    search_regex: file c.*
+  register: wait_regex_match_absent_existing
+
+- name: assert wait for file content to not match regex
+  assert:
+    that:
+    - wait_regex_match_absent_existing.attempts == 1
+
+- name: remove file to test search_regex works on missing files
+  win_file:
+    path: '{{test_win_wait_for_path}}\test.txt'
+    state: absent
+
+- name: wait for file content to not match regex - missing file
+  win_wait_for:
+    path: '{{test_win_wait_for_path}}\test.txt'
+    state: absent
+    search_regex: file c.*
+  register: wait_regex_match_absent_missing
+
+- name: assert wait for file content to not match regex - missing file
+  assert:
+    that:
+    - wait_regex_match_absent_missing.attempts == 1
+
+# port tests
+- name: timeout waiting for port to come online
+  win_wait_for:
+    port: '{{test_win_wait_for_port}}'
+    timeout: 5
+    state: started
+  register: fail_timeout_port_online
+  ignore_errors: True
+
+- name: assert timeout while waiting for port to come online
+  assert:
+    that:
+    - "fail_timeout_port_online.msg == 'timeout while waiting for 127.0.0.1:' + test_win_wait_for_port|string + ' to start listening'"
+    - fail_timeout_port_online.attempts > 1
+    - fail_timeout_port_online.elapsed > 5
+
+- name: run async task to start web server
+  win_shell: Start-Sleep -Seconds 5; {{test_win_wait_for_path}}\http-server.ps1
+  async: 30
+  poll: 0
+
+- name: wait for port to come online
+  win_wait_for:
+    port: '{{test_win_wait_for_port}}'
+    state: started
+  register: wait_for_port_to_start
+
+- name: assert wait for port to come online
+  assert:
+    that:
+    - wait_for_port_to_start.attempts > 1
+
+- name: start web server
+  win_shell: '{{test_win_wait_for_path}}\http-server.ps1'
+  async: 30
+  poll: 0
+
+- name: wait for port that is already online
+  win_wait_for:
+    port: '{{test_win_wait_for_port}}'
+    state: started
+  register: wait_for_port_already_started
+
+- name: assert wait for port that is already online
+  assert:
+    that:
+    - wait_for_port_already_started.attempts == 1
+
+- name: wait for port that is already offline
+  win_wait_for:
+    port: '{{test_win_wait_for_port}}'
+    state: stopped
+  register: wait_for_port_already_stopped
+
+- name: assert wait for port that is already offline
+  assert:
+    that:
+    - wait_for_port_already_stopped.attempts == 1
+
+- name: start web server for offline port test
+  win_shell: '{{test_win_wait_for_path}}\http-server.ps1'
+  async: 30
+  poll: 0
+
+- name: wait for port to go offline
+  win_wait_for:
+    port: '{{test_win_wait_for_port}}'
+    state: stopped
+  register: wait_for_port_to_be_stopped
+
+- name: assert wait for port to go offline
+  assert:
+    that:
+    - wait_for_port_to_be_stopped.attempts > 1
+
+- name: wait for offline port to be drained
+  win_wait_for:
+    port: '{{test_win_wait_for_port}}'
+    state: drained
+  register: wait_for_drained_port_no_port
+
+- name: assert wait for offline port to be drained
+  assert:
+    that:
+    - wait_for_drained_port_no_port.attempts == 1
+
+- name: clear testing folder
+  win_file:
+    path: '{{test_win_wait_for_path}}'
+    state: absent
diff --git a/test/integration/targets/win_wait_for/templates/http-server.ps1 b/test/integration/targets/win_wait_for/templates/http-server.ps1
new file mode 100644
index 00000000000..dd1f9818090
--- /dev/null
+++ b/test/integration/targets/win_wait_for/templates/http-server.ps1
@@ -0,0 +1,22 @@
+$ErrorActionPreference = 'Stop'
+
+$port = {{test_win_wait_for_port}}
+
+$endpoint = New-Object -TypeName System.Net.IPEndPoint([System.Net.IPAddress]::Parse("0.0.0.0"), $port)
+$listener = New-Object -TypeName System.Net.Sockets.TcpListener($endpoint)
+$listener.Server.ReceiveTimeout = 3000
+$listener.Start()
+
+try {
+    while ($true) {
+        if (-not $listener.Pending()) {
+            Start-Sleep -Seconds 1
+        } else {
+            $client = $listener.AcceptTcpClient()
+            $client.Close()
+            break
+        }
+    }
+} finally {
+    $listener.Stop()
+}