diff --git a/lua/plenary/curl.lua b/lua/plenary/curl.lua
index 7f4eef8c..2a052b77 100644
--- a/lua/plenary/curl.lua
+++ b/lua/plenary/curl.lua
@@ -32,6 +32,7 @@ local util, parse, request = {}, {}, nil
 local F = require "plenary.functional"
 local J = require "plenary.job"
 local P = require "plenary.path"
+local S = require "plenary.system"
 
 -- Utils ----------------------------------------------------
 -------------------------------------------------------------
@@ -70,7 +71,7 @@ util.gen_dump_path = function()
     local v = (l == "x") and math.random(0, 0xf) or math.random(0, 0xb)
     return string.format("%x", v)
   end)
-  if P.path.sep == "\\" then
+  if S.is_windows() then
     path = string.format("%s\\AppData\\Local\\Temp\\plenary_curl_%s.headers", os.getenv "USERPROFILE", id)
   else
     path = "/tmp/plenary_curl_" .. id .. ".headers"
diff --git a/lua/plenary/path.lua b/lua/plenary/path.lua
index f92b26e7..a54692db 100644
--- a/lua/plenary/path.lua
+++ b/lua/plenary/path.lua
@@ -7,6 +7,7 @@ local bit = require "plenary.bit"
 local uv = vim.loop
 
 local F = require "plenary.functional"
+local S = require "plenary.system"
 
 local S_IF = {
   -- S_IFDIR  = 0o040000  # directory
@@ -20,8 +21,7 @@ path.home = vim.loop.os_homedir()
 
 path.sep = (function()
   if jit then
-    local os = string.lower(jit.os)
-    if os ~= "windows" then
+    if not S.is_windows() or S.uses_shellslash() then
       return "/"
     else
       return "\\"
@@ -32,7 +32,7 @@ path.sep = (function()
 end)()
 
 path.root = (function()
-  if path.sep == "/" then
+  if not S.is_windows() or S.uses_shellslash then
     return function()
       return "/"
     end
@@ -55,7 +55,7 @@ local concat_paths = function(...)
 end
 
 local function is_root(pathname)
-  if path.sep == "\\" then
+  if S.is_windows() then
     return string.match(pathname, "^[A-Z]:\\?$")
   end
   return pathname == "/"
@@ -77,7 +77,7 @@ local is_uri = function(filename)
 end
 
 local is_absolute = function(filename, sep)
-  if sep == "\\" then
+  if S.is_windows() then
     return string.match(filename, "^[%a]:\\.*$") ~= nil
   end
   return string.sub(filename, 1, 1) == sep
@@ -103,7 +103,7 @@ local function _normalize_path(filename, cwd)
     local split_without_disk_name = function(filename_local)
       local parts = _split_by_separator(filename_local)
       -- Remove disk name part on Windows
-      if path.sep == "\\" and is_abs then
+      if S.is_windows() and is_abs then
         table.remove(parts, 1)
       end
       return parts
@@ -431,7 +431,7 @@ local function shorten_len(filename, len, exclude)
 end
 
 local shorten = (function()
-  if jit and path.sep ~= "\\" then
+  if jit and not S.is_windows() then
     local ffi = require "ffi"
     ffi.cdef [[
     typedef unsigned char char_u;
diff --git a/lua/plenary/scandir.lua b/lua/plenary/scandir.lua
index 16e4ed54..80850408 100644
--- a/lua/plenary/scandir.lua
+++ b/lua/plenary/scandir.lua
@@ -1,6 +1,7 @@
 local Path = require "plenary.path"
 local os_sep = Path.path.sep
 local F = require "plenary.functional"
+local S = require "plenary.system"
 
 local uv = vim.loop
 
@@ -319,7 +320,7 @@ local gen_date = (function()
 end)()
 
 local get_username = (function()
-  if jit and os_sep ~= "\\" then
+  if jit and not S.is_windows() then
     local ffi = require "ffi"
     ffi.cdef [[
       typedef unsigned int __uid_t;
@@ -369,7 +370,7 @@ local get_username = (function()
 end)()
 
 local get_groupname = (function()
-  if jit and os_sep ~= "\\" then
+  if jit and not S.is_windows() then
     local ffi = require "ffi"
     ffi.cdef [[
       typedef unsigned int __gid_t;
@@ -446,8 +447,8 @@ local gen_ls = function(data, path, opts)
 
   local results, sections = {}, {}
 
-  local users_tbl = os_sep ~= "\\" and {} or nil
-  local groups_tbl = os_sep ~= "\\" and {} or nil
+  local users_tbl = not S.is_windows() and {} or nil
+  local groups_tbl = not S.is_windows() and {} or nil
 
   local stats, permissions_cache = {}, {}
   for _, v in ipairs(data) do
diff --git a/lua/plenary/strings.lua b/lua/plenary/strings.lua
index bc374739..3b1828c2 100644
--- a/lua/plenary/strings.lua
+++ b/lua/plenary/strings.lua
@@ -1,9 +1,10 @@
 local path = require("plenary.path").path
+local S = require "plenary.system"
 
 local M = {}
 
 M.strdisplaywidth = (function()
-  if jit and path.sep ~= [[\]] then
+  if jit and not S.is_windows() then
     local ffi = require "ffi"
     ffi.cdef [[
       typedef unsigned char char_u;
@@ -29,7 +30,7 @@ M.strdisplaywidth = (function()
 end)()
 
 M.strcharpart = (function()
-  if jit and path.sep ~= [[\]] then
+  if jit and not S.is_windows() then
     local ffi = require "ffi"
     ffi.cdef [[
       typedef unsigned char char_u;
diff --git a/lua/plenary/system.lua b/lua/plenary/system.lua
new file mode 100644
index 00000000..e04b0cf2
--- /dev/null
+++ b/lua/plenary/system.lua
@@ -0,0 +1,22 @@
+local system = {}
+
+function system.is_windows()
+    -- The shellslash option is not able to change this variable
+    if package.config:sub(1,1) == "\\" then
+        return true
+    end
+
+    return false
+end
+
+function system.uses_shellslash()
+    local shellslash_exists = vim.fn.exists("+shellslash") ~= 0
+
+    if shellslash_exists then
+        return vim.o.shellslash
+    end
+
+    return false
+end
+
+return system
diff --git a/tests/plenary/path_spec.lua b/tests/plenary/path_spec.lua
index f5a90972..f64cab61 100644
--- a/tests/plenary/path_spec.lua
+++ b/tests/plenary/path_spec.lua
@@ -1,5 +1,6 @@
 local Path = require "plenary.path"
 local path = Path.path
+local System = require "plenary.system"
 
 describe("Path", function()
   it("should find valid files", function()
@@ -104,7 +105,7 @@ describe("Path", function()
     end)
 
     it("can take absolute paths and make them relative to a given path", function()
-      local root = path.sep == "\\" and "c:\\" or "/"
+      local root = System.is_windows() and "c:\\" or "/"
       local r = Path:new { root, "home", "prime" }
       local p = Path:new { "aoeu", "agen.lua" }
       local absolute = r.filename .. path.sep .. p.filename
@@ -120,7 +121,7 @@ describe("Path", function()
     end)
 
     it("can take double separator absolute paths and make them relative to a given path", function()
-      local root = path.sep == "\\" and "c:\\" or "/"
+      local root = System.is_windows() and "c:\\" or "/"
       local r = Path:new { root, "home", "prime" }
       local p = Path:new { "aoeu", "agen.lua" }
       local absolute = r.filename .. path.sep .. path.sep .. p.filename
@@ -129,7 +130,7 @@ describe("Path", function()
     end)
 
     it("can take absolute paths and make them relative to a given path with trailing separator", function()
-      local root = path.sep == "\\" and "c:\\" or "/"
+      local root = System.is_windows() and "c:\\" or "/"
       local r = Path:new { root, "home", "prime" }
       local p = Path:new { "aoeu", "agen.lua" }
       local absolute = r.filename .. path.sep .. p.filename
@@ -138,7 +139,7 @@ describe("Path", function()
     end)
 
     it("can take absolute paths and make them relative to the root directory", function()
-      local root = path.sep == "\\" and "c:\\" or "/"
+      local root = System.is_windows() and "c:\\" or "/"
       local p = Path:new { "home", "prime", "aoeu", "agen.lua" }
       local absolute = root .. p.filename
       local relative = Path:new(absolute):make_relative(root)
@@ -146,7 +147,7 @@ describe("Path", function()
     end)
 
     it("can take absolute paths and make them relative to themselves", function()
-      local root = path.sep == "\\" and "c:\\" or "/"
+      local root = System.is_windows() and "c:\\" or "/"
       local p = Path:new { root, "home", "prime", "aoeu", "agen.lua" }
       local relative = Path:new(p.filename):make_relative(p.filename)
       assert.are.same(relative, ".")