diff --git a/changelogs/fragments/win_find-paths.yaml b/changelogs/fragments/win_find-paths.yaml
new file mode 100644
index 0000000000..a113a72ed1
--- /dev/null
+++ b/changelogs/fragments/win_find-paths.yaml
@@ -0,0 +1,3 @@
+bugfixes:
+- win_find - Fix issues when using paths with glob like characters, e.g. ``[``, ``]``
+- win_find - Ensure found files are sorted alphabetically by the path instead of it being random
diff --git a/lib/ansible/modules/windows/win_find.ps1 b/lib/ansible/modules/windows/win_find.ps1
index f2095e09bf..da8c62842d 100644
--- a/lib/ansible/modules/windows/win_find.ps1
+++ b/lib/ansible/modules/windows/win_find.ps1
@@ -78,13 +78,13 @@ $env:TMP = $original_tmp
 Function Assert-Age($info) {
     $valid_match = $true
 
-    if ($age -ne $null) {
+    if ($null -ne $age) {
         $seconds_per_unit = @{'s'=1; 'm'=60; 'h'=3600; 'd'=86400; 'w'=604800}
         $seconds_pattern = '^(-?\d+)(s|m|h|d|w)?$'
         $match = $age -match $seconds_pattern
         if ($match) {
             [int]$specified_seconds = $matches[1]
-            if ($matches[2] -eq $null) {
+            if ($null -eq $matches[2]) {
                 $chosen_unit = 's'
             } else {
                 $chosen_unit = $matches[2]
@@ -148,7 +148,7 @@ Function Assert-Hidden($info) {
 Function Assert-Pattern($info) {
     $valid_match = $false
 
-    if ($patterns -ne $null) {
+    if ($null -ne $patterns) {
         foreach ($pattern in $patterns) {
             if ($use_regex -eq $true) {
                 # Use -match for regex matching
@@ -172,13 +172,13 @@ Function Assert-Pattern($info) {
 Function Assert-Size($info) {
     $valid_match = $true
 
-    if ($size -ne $null) {
+    if ($null -ne $size) {
         $bytes_per_unit = @{'b'=1; 'k'=1024; 'm'=1024*1024; 'g'=1024*1024*1024; 't'=1024*1024*1024*1024}
         $size_pattern = '^(-?\d+)(b|k|m|g|t)?$'
         $match = $size -match $size_pattern
         if ($match) {
             [int]$specified_size = $matches[1] 
-            if ($matches[2] -eq $null) {
+            if ($null -eq $matches[2]) {
                 $chosen_byte = 'b'
             } else {
                 $chosen_byte = $matches[2]
@@ -255,19 +255,24 @@ Function Get-FileStat($file) {
         $isdir = $true
 
         $share_info = Get-WmiObject -Class Win32_Share -Filter "Path='$($file.Fullname -replace '\\', '\\')'"
-        if ($share_info -ne $null) {
+        if ($null -ne $share_info) {
             $isshared = $true
             $file_stat.sharename = $share_info.Name
         }
         
         # only get the size of a directory if there are files (not directories) inside the folder
-        $dir_files_sum = Get-ChildItem $file.FullName -Recurse | Where-Object { -not $_.PSIsContainer }
+        # Get-ChildItem -LiteralPath does not work properly on older OS', use .NET instead
+        $dir_files = @()
+        try {
+            $dir_files = $file.EnumerateFiles("*", [System.IO.SearchOption]::AllDirectories)
+        } catch [System.IO.DirectoryNotFoundException] { # Broken ReparsePoint/Symlink, cannot enumerate
+        } catch [System.UnauthorizedAccessException] {}  # No ListDirectory permissions, Get-ChildItem ignored this
 
-        if ($dir_files_sum -eq $null -or ($dir_files_sum.PSObject.Properties.name -contains 'length' -eq $false)) {
-            $file_stat.size = 0
-        } else {
-            $file_stat.size = ($dir_files_sum | Measure-Object -property length -sum).Sum
+        $size = 0
+        foreach ($dir_file in $dir_files) {
+            $size += $dir_file.Length
         }
+        $file_stat.size = $size
     } else {
         $file_stat.size = $file.length
         $file_stat.extension = $file.Extension
@@ -291,8 +296,17 @@ Function Get-FileStat($file) {
 
 Function Get-FilesInFolder($path) {
     $items = @()
-    foreach ($item in (Get-ChildItem -Force -Path $path -ErrorAction SilentlyContinue)) {
-        if ($item.PSIsContainer -and $recurse) {
+
+    # Get-ChildItem -LiteralPath can bomb out on older OS', use .NET instead
+    $dir = New-Object -TypeName System.IO.DirectoryInfo -ArgumentList $path
+    $dir_files = @()
+    try {
+        $dir_files = $dir.EnumerateFileSystemInfos("*", [System.IO.SearchOption]::TopDirectoryOnly)
+    } catch [System.IO.DirectoryNotFoundException] { # Broken ReparsePoint/Symlink, cannot enumerate
+    } catch [System.UnauthorizedAccessException] {}  # No ListDirectory permissions, Get-ChildItem ignored this
+
+    foreach ($item in $dir_files) {
+        if ($item -is [System.IO.DirectoryInfo] -and $recurse) {
             if (($item.Attributes -like '*ReparsePoint*' -and $follow) -or ($item.Attributes -notlike '*ReparsePoint*')) {
                 # File is a link and we want to follow a link OR file is not a link
                 $items += $item.FullName
@@ -311,8 +325,8 @@ Function Get-FilesInFolder($path) {
 
 $paths_to_check = @()
 foreach ($path in $paths) {
-    if (Test-Path $path) {
-        if ((Get-Item -Force $path).PSIsContainer) {
+    if (Test-Path -LiteralPath $path) {
+        if ((Get-Item -LiteralPath $path -Force).PSIsContainer) {
             $paths_to_check += Get-FilesInFolder -path $path
         } else {
             Fail-Json $result "Argument path $path is a file not a directory"
@@ -321,11 +335,11 @@ foreach ($path in $paths) {
         Fail-Json $result "Argument path $path does not exist cannot get information on"
     }
 }
-$paths_to_check = $paths_to_check | Select-Object -Unique
+$paths_to_check = $paths_to_check | Select-Object -Unique | Sort-Object
 
 foreach ($path in $paths_to_check) {
     try {
-        $file = Get-Item -Force -Path $path
+        $file = Get-Item -LiteralPath $path -Force
         $info = Get-FileStat -file $file
     } catch {
         Add-Warning -obj $result -message "win_find failed to check some files, these files were ignored and will not be part of the result output"
diff --git a/lib/ansible/modules/windows/win_find.py b/lib/ansible/modules/windows/win_find.py
index 5954891ff4..31ffb799b6 100644
--- a/lib/ansible/modules/windows/win_find.py
+++ b/lib/ansible/modules/windows/win_find.py
@@ -214,7 +214,8 @@ matched:
     type: int
     sample: 2
 files:
-    description: Information on the files/folders that match the criteria returned as a list of dictionary elements for each file matched.
+    description: Information on the files/folders that match the criteria returned as a list of dictionary elements
+      for each file matched. The entries are sorted by the path value alphabetically.
     returned: success
     type: complex
     contains:
diff --git a/test/integration/targets/win_find/defaults/main.yml b/test/integration/targets/win_find/defaults/main.yml
index d04ec5f422..fc2e2e1179 100644
--- a/test/integration/targets/win_find/defaults/main.yml
+++ b/test/integration/targets/win_find/defaults/main.yml
@@ -1,2 +1,2 @@
-win_find_dir: "{{win_output_dir}}\\win_find"
+win_find_dir: '{{ win_output_dir }}\win_find .ÅÑŚÌβŁÈ [$!@^&test(;)]'
 test_win_find_username: testuser
diff --git a/test/integration/targets/win_find/tasks/main.yml b/test/integration/targets/win_find/tasks/main.yml
index a44d5217c3..c2f40a8fde 100644
--- a/test/integration/targets/win_find/tasks/main.yml
+++ b/test/integration/targets/win_find/tasks/main.yml
@@ -22,8 +22,10 @@
         "emptynested\nest\dir1",
         "emptynested\nest\dir2"
     )
+
+    $tmp_dir = '{{ win_find_dir }}'
     foreach ($directory in $directories) {
-        New-Item -Path "{{win_find_dir}}\$directory" -ItemType Directory
+        New-Item -Path "$tmp_dir\$directory" -ItemType Directory
     }
 
     $normal_content = "abcdefg1234567"
@@ -42,40 +44,42 @@
         "hard-link-dest\file-abc.log"
     )
     foreach ($file in $normal_files) {
-        New-Item -Path "{{win_find_dir}}\$file" -ItemType File
-        [System.IO.File]::WriteAllText("{{win_find_dir}}\$file", $normal_content)
+        New-Item -Path "$tmp_dir\$file" -ItemType File
+        [System.IO.File]::WriteAllText("$tmp_dir\$file", $normal_content)
     }
 
-    New-Item -Path "{{win_find_dir}}\single\small.ps1" -ItemType File
-    [System.IO.File]::WriteAllText("{{win_find_dir}}\single\small.ps1", "a")
+    New-Item -Path "$tmp_dir\single\small.ps1" -ItemType File
+    [System.IO.File]::WriteAllText("$tmp_dir\single\small.ps1", "a")
 
-    New-Item -Path "{{win_find_dir}}\date\new.ps1" -ItemType File
-    [System.IO.File]::WriteAllText("{{win_find_dir}}\date\new.ps1", "random text for new date")
+    New-Item -Path "$tmp_dir\date\new.ps1" -ItemType File
+    [System.IO.File]::WriteAllText("$tmp_dir\date\new.ps1", "random text for new date")
 
-    New-Item -Path "{{win_find_dir}}\date\old.ps1" -ItemType File
-    [System.IO.File]::WriteAllText("{{win_find_dir}}\date\old.ps1", "random text for old date")
+    New-Item -Path "$tmp_dir\date\old.ps1" -ItemType File
+    [System.IO.File]::WriteAllText("$tmp_dir\date\old.ps1", "random text for old date")
 
-    New-Item -Path "{{win_find_dir}}\single\large.ps1" -ItemType File
-    Set-Content -Path "{{win_find_dir}}\single\large.ps1" -Value ('abcdefghijklmnopqrstuvwxyz' * 10000)
+    New-Item -Path "$tmp_dir\single\large.ps1" -ItemType File
+    Set-Content -LiteralPath "$tmp_dir\single\large.ps1" -Value ('abcdefghijklmnopqrstuvwxyz' * 10000)
 
     $share_stat = Get-WmiObject -Class Win32_Share -Filter "name='folder-share'"
     if ($share_stat) {
         $share_stat.Delete()
     }
     $wmi = [wmiClass] 'Win32_Share'
-    $wmi.Create("{{win_find_dir}}\shared\folder", "folder-share", 0)
+    $wmi.Create("$tmp_dir\shared\folder", "folder-share", 0)
+
+    cmd.exe /c mklink /D "$tmp_dir\nested\link" "$tmp_dir\link-dest"
+    cmd.exe /c mklink /D "$tmp_dir\broken-link" "$tmp_dir\broken-link-dest"
+    cmd.exe /c mklink /H "$tmp_dir\hard-link-dest\hard-link.log" "$tmp_dir\hard-link-dest\file-abc.log"
+    cmd.exe /c mklink /J "$tmp_dir\junction-link" "$tmp_dir\junction-link-dest"
 
-    cmd.exe /c mklink /D "{{win_find_dir}}\nested\link" "{{win_find_dir}}\link-dest"
-    cmd.exe /c mklink /D "{{win_find_dir}}\broken-link" "{{win_find_dir}}\broken-link-dest"
-    cmd.exe /c mklink /H "{{win_find_dir}}\hard-link-dest\hard-link.log" "{{win_find_dir}}\hard-link-dest\file-abc.log"
-    cmd.exe /c mklink /J "{{win_find_dir}}\junction-link" "{{win_find_dir}}\junction-link-dest"
-  
     $date = Get-Date -Year 2016 -Month 11 -Day 1 -Hour 7 -Minute 10 -Second 5 -Millisecond 0
-    Get-ChildItem -Path "{{win_find_dir}}" -Recurse | Where-Object { $_.Name -ne "new.ps1" } | ForEach-Object {
+    Set-Location -LiteralPath $tmp_dir
+    Get-ChildItem -Recurse | Where-Object { $_.Name -ne "new.ps1" } | ForEach-Object {
         $_.CreationTime = $date
         $_.LastAccessTime = $date
         $_.LastWriteTime = $date
     }
+    Pop-Location
 
     $attributes = @{
         "hidden" = "Hidden"
@@ -85,7 +89,7 @@
         "single\hidden.ps1" = "Hidden"
     }
     foreach ($attribute in $attributes.GetEnumerator()) {
-        $item = Get-Item -Path "{{win_find_dir}}\$($attribute.Name)"
+        $item = Get-Item -LiteralPath "$tmp_dir\$($attribute.Name)"
         $file_attributes = $item.Attributes -split ','
         if ($file_attributes -notcontains $attribute.Value) {
             $file_attributes += $attribute.Value
@@ -93,7 +97,7 @@
         $item.Attributes = $file_attributes -join ','
     }
 
-    Remove-Item -Path "{{win_find_dir}}\broken-link-dest" -Force
+    Remove-Item -LiteralPath "$tmp_dir\broken-link-dest" -Force
 
 - block:
   - include_tasks: tests.yml
diff --git a/test/integration/targets/win_find/tasks/tests.yml b/test/integration/targets/win_find/tasks/tests.yml
index 0afe771946..8c4a7ebacc 100644
--- a/test/integration/targets/win_find/tasks/tests.yml
+++ b/test/integration/targets/win_find/tasks/tests.yml
@@ -7,19 +7,19 @@
 
 - name: expect failure when setting paths to a file
   win_find:
-    paths: "{{win_output_dir}}\\win_find\\single\\large.ps1"
+    paths: "{{win_find_dir}}\\single\\large.ps1"
   register: actual
-  failed_when: actual.msg != 'Argument path ' + win_output_dir + '\\win_find\\single\\large.ps1 is a file not a directory'
+  failed_when: actual.msg != 'Argument path ' + win_find_dir + '\\single\\large.ps1 is a file not a directory'
 
 - name: expect failure when path is set to a non existent folder
   win_find:
-    paths: "{{win_output_dir}}\\win_find\\thisisafakefolder"
+    paths: "{{win_find_dir}}\\thisisafakefolder"
   register: actual
-  failed_when: actual.msg != 'Argument path ' + win_output_dir + '\\win_find\\thisisafakefolder does not exist cannot get information on'
+  failed_when: actual.msg != 'Argument path ' + win_find_dir + '\\thisisafakefolder does not exist cannot get information on'
 
 - name: get files in single directory
   win_find:
-    paths: "{{win_output_dir}}\\win_find\\single"
+    paths: "{{win_find_dir}}\\single"
   register: actual
 
 - name: set expected value for files in a single directory
@@ -192,22 +192,6 @@
       examined: 8
       failed: False
       files:
-      - { isarchive: True,
-          attributes: Archive,
-          checksum: 8df33cee3325596517df5bb5aa980cf9c5c1fda3,
-          creationtime: 1477984205,
-          extension: .ps1,
-          filename: test.ps1,
-          ishidden: False,
-          isdir: False,
-          islnk: False,
-          lastaccesstime: 1477984205,
-          lastwritetime: 1477984205,
-          owner: BUILTIN\Administrators,
-          path: "{{win_find_dir}}\\nested\\sub-nest\\test.ps1",
-          isreadonly: False,
-          isshared: False,
-          size: 14 }
       - { isarchive: True,
           attributes: Archive,
           checksum: 8df33cee3325596517df5bb5aa980cf9c5c1fda3,
@@ -224,6 +208,22 @@
           isreadonly: False,
           isshared: False,
           size: 14 }
+      - { isarchive: True,
+          attributes: Archive,
+          checksum: 8df33cee3325596517df5bb5aa980cf9c5c1fda3,
+          creationtime: 1477984205,
+          extension: .ps1,
+          filename: test.ps1,
+          ishidden: False,
+          isdir: False,
+          islnk: False,
+          lastaccesstime: 1477984205,
+          lastwritetime: 1477984205,
+          owner: BUILTIN\Administrators,
+          path: "{{win_find_dir}}\\nested\\sub-nest\\test.ps1",
+          isreadonly: False,
+          isshared: False,
+          size: 14 }
       - { isarchive: True,
           attributes: Archive,
           checksum: 8df33cee3325596517df5bb5aa980cf9c5c1fda3,
@@ -261,6 +261,22 @@
       examined: 10
       failed: False
       files:
+      - { isarchive: True,
+          attributes: Archive,
+          checksum: 8df33cee3325596517df5bb5aa980cf9c5c1fda3,
+          creationtime: 1477984205,
+          extension: .ps1,
+          filename: file.ps1,
+          ishidden: False,
+          isdir: False,
+          islnk: False,
+          lastaccesstime: 1477984205,
+          lastwritetime: 1477984205,
+          owner: BUILTIN\Administrators,
+          path: "{{win_find_dir}}\\nested\\file.ps1",
+          isreadonly: False,
+          isshared: False,
+          size: 14 }
       - { isarchive: True,
           attributes: Archive,
           checksum: 8df33cee3325596517df5bb5aa980cf9c5c1fda3,
@@ -293,22 +309,6 @@
           isreadonly: False,
           isshared: False,
           size: 14 }
-      - { isarchive: True,
-          attributes: Archive,
-          checksum: 8df33cee3325596517df5bb5aa980cf9c5c1fda3,
-          creationtime: 1477984205,
-          extension: .ps1,
-          filename: file.ps1,
-          ishidden: False,
-          isdir: False,
-          islnk: False,
-          lastaccesstime: 1477984205,
-          lastwritetime: 1477984205,
-          owner: BUILTIN\Administrators,
-          path: "{{win_find_dir}}\\nested\\file.ps1",
-          isreadonly: False,
-          isshared: False,
-          size: 14 }
       - { isarchive: True,
           attributes: Archive,
           checksum: 8df33cee3325596517df5bb5aa980cf9c5c1fda3,