diff --git a/lua/telescope/actions/history.lua b/lua/telescope/actions/history.lua
index 2b08689642..1233b34f99 100644
--- a/lua/telescope/actions/history.lua
+++ b/lua/telescope/actions/history.lua
@@ -1,5 +1,5 @@
 local conf = require("telescope.config").values
-local Path = require "plenary.path"
+local Path = require "plenary.path2"
 local utils = require "telescope.utils"
 
 local uv = vim.loop
diff --git a/lua/telescope/actions/set.lua b/lua/telescope/actions/set.lua
index b37c1e874a..f4d71fbf02 100644
--- a/lua/telescope/actions/set.lua
+++ b/lua/telescope/actions/set.lua
@@ -14,7 +14,7 @@
 local a = vim.api
 
 local log = require "telescope.log"
-local Path = require "plenary.path"
+local Path = require "plenary.path2"
 local state = require "telescope.state"
 local utils = require "telescope.utils"
 
diff --git a/lua/telescope/actions/utils.lua b/lua/telescope/actions/utils.lua
index 81bd870bfc..31f8156585 100644
--- a/lua/telescope/actions/utils.lua
+++ b/lua/telescope/actions/utils.lua
@@ -108,7 +108,7 @@ end
 
 -- Best effort to infer function names for actions.which_key
 function utils._get_anon_function_name(info)
-  local Path = require "plenary.path"
+  local Path = require "plenary.path2"
   local fname
   -- if fn defined in string (ie loadstring) source is string
   -- if fn defined in file, source is file name prefixed with a `@´
diff --git a/lua/telescope/algos/fzy.lua b/lua/telescope/algos/fzy.lua
index bf322ab437..22c564fecb 100644
--- a/lua/telescope/algos/fzy.lua
+++ b/lua/telescope/algos/fzy.lua
@@ -7,14 +7,7 @@
 -- > matches on consecutive letters and starts of words. This allows matching
 -- > using acronyms or different parts of the path." - J Hawthorn
 
-local has_path, Path = pcall(require, "plenary.path")
-if not has_path then
-  Path = {
-    path = {
-      separator = "/",
-    },
-  }
-end
+local Path = require "plenary.path2"
 
 local SCORE_GAP_LEADING = -0.005
 local SCORE_GAP_TRAILING = -0.005
diff --git a/lua/telescope/builtin/__files.lua b/lua/telescope/builtin/__files.lua
index cc5f905c0f..bd2ff03a66 100644
--- a/lua/telescope/builtin/__files.lua
+++ b/lua/telescope/builtin/__files.lua
@@ -10,7 +10,7 @@ local utils = require "telescope.utils"
 local conf = require("telescope.config").values
 local log = require "telescope.log"
 
-local Path = require "plenary.path"
+local Path = require "plenary.path2"
 
 local flatten = utils.flatten
 local filter = vim.tbl_filter
diff --git a/lua/telescope/builtin/__git.lua b/lua/telescope/builtin/__git.lua
index 1b6e9ed2dd..841273fd6d 100644
--- a/lua/telescope/builtin/__git.lua
+++ b/lua/telescope/builtin/__git.lua
@@ -8,7 +8,7 @@ local previewers = require "telescope.previewers"
 local utils = require "telescope.utils"
 local entry_display = require "telescope.pickers.entry_display"
 local strings = require "plenary.strings"
-local Path = require "plenary.path"
+local Path = require "plenary.path2"
 
 local conf = require("telescope.config").values
 local git_command = utils.__git_command
diff --git a/lua/telescope/builtin/__internal.lua b/lua/telescope/builtin/__internal.lua
index d7d74e7c8f..7578d67629 100644
--- a/lua/telescope/builtin/__internal.lua
+++ b/lua/telescope/builtin/__internal.lua
@@ -3,7 +3,7 @@ local action_set = require "telescope.actions.set"
 local action_state = require "telescope.actions.state"
 local finders = require "telescope.finders"
 local make_entry = require "telescope.make_entry"
-local Path = require "plenary.path"
+local Path = require "plenary.path2"
 local pickers = require "telescope.pickers"
 local previewers = require "telescope.previewers"
 local p_window = require "telescope.pickers.window"
@@ -319,7 +319,7 @@ internal.symbols = function(opts)
 
   local results = {}
   for _, source in ipairs(sources) do
-    local data = vim.json.decode(Path:new(source):read())
+    local data = vim.json.decode(assert(Path:new(source):read()))
     for _, entry in ipairs(data) do
       table.insert(results, entry)
     end
diff --git a/lua/telescope/config.lua b/lua/telescope/config.lua
index 716141664c..b8d6dd18f0 100644
--- a/lua/telescope/config.lua
+++ b/lua/telescope/config.lua
@@ -1,7 +1,7 @@
 local strings = require "plenary.strings"
 local deprecated = require "telescope.deprecated"
 local sorters = require "telescope.sorters"
-local os_sep = require("plenary.path").path.sep
+local os_sep = require("plenary.path2").path.sep
 local has_win = vim.fn.has "win32" == 1
 
 -- Keep the values around between reloads
diff --git a/lua/telescope/make_entry.lua b/lua/telescope/make_entry.lua
index a1806f37d4..0e0a08dba6 100644
--- a/lua/telescope/make_entry.lua
+++ b/lua/telescope/make_entry.lua
@@ -37,7 +37,7 @@
 local entry_display = require "telescope.pickers.entry_display"
 local utils = require "telescope.utils"
 local strings = require "plenary.strings"
-local Path = require "plenary.path"
+local Path = require "plenary.path2"
 
 local treesitter_type_highlight = {
   ["associated"] = "TSConstant",
diff --git a/lua/telescope/previewers/buffer_previewer.lua b/lua/telescope/previewers/buffer_previewer.lua
index 18f483df18..942eb5f50e 100644
--- a/lua/telescope/previewers/buffer_previewer.lua
+++ b/lua/telescope/previewers/buffer_previewer.lua
@@ -1,5 +1,5 @@
 local from_entry = require "telescope.from_entry"
-local Path = require "plenary.path"
+local Path = require "plenary.path2"
 local utils = require "telescope.utils"
 local putils = require "telescope.previewers.utils"
 local Previewer = require "telescope.previewers.previewer"
@@ -98,7 +98,7 @@ color_hash[6] = function(line)
 end
 
 local colorize_ls_long = function(bufnr, data, sections)
-  local windows_add = Path.path.sep == "\\" and 2 or 0
+  local windows_add = utils.iswin and 2 or 0
   for lnum, line in ipairs(data) do
     local section = sections[lnum]
     for i = 1, section[1].end_index - 1 do -- Highlight permissions
@@ -125,7 +125,7 @@ local handle_directory_preview = function(filepath, bufnr, opts)
   local set_colorize_lines
   if opts.preview.ls_short then
     set_colorize_lines = function(data, sections)
-      local PATH_SECTION = Path.path.sep == "\\" and 4 or 6
+      local PATH_SECTION = utils.iswin and 4 or 6
       local paths = {}
       for i, line in ipairs(data) do
         local section = sections[i][PATH_SECTION]
@@ -195,7 +195,7 @@ local handle_file_preview = function(filepath, bufnr, stat, opts)
     end
 
     opts.start_time = vim.loop.hrtime()
-    Path:new(filepath):_read_async(vim.schedule_wrap(function(data)
+    Path:new(filepath):read(vim.schedule_wrap(function(data)
       if not vim.api.nvim_buf_is_valid(bufnr) then
         return
       end
diff --git a/lua/telescope/previewers/term_previewer.lua b/lua/telescope/previewers/term_previewer.lua
index bf6f40c85a..d4fa650411 100644
--- a/lua/telescope/previewers/term_previewer.lua
+++ b/lua/telescope/previewers/term_previewer.lua
@@ -1,6 +1,6 @@
 local conf = require("telescope.config").values
 local utils = require "telescope.utils"
-local Path = require "plenary.path"
+local Path = require "plenary.path2"
 local from_entry = require "telescope.from_entry"
 local Previewer = require "telescope.previewers.previewer"
 local putil = require "telescope.previewers.utils"
diff --git a/lua/telescope/previewers/utils.lua b/lua/telescope/previewers/utils.lua
index b430e5a509..b6f91b9c99 100644
--- a/lua/telescope/previewers/utils.lua
+++ b/lua/telescope/previewers/utils.lua
@@ -3,7 +3,7 @@ local strings = require "plenary.strings"
 local conf = require("telescope.config").values
 
 local Job = require "plenary.job"
-local Path = require "plenary.path"
+local Path = require "plenary.path2"
 
 local telescope_utils = require "telescope.utils"
 
diff --git a/lua/telescope/testharness/init.lua b/lua/telescope/testharness/init.lua
index 9a8e707388..6645484865 100644
--- a/lua/telescope/testharness/init.lua
+++ b/lua/telescope/testharness/init.lua
@@ -1,6 +1,6 @@
 local assert = require "luassert"
 
-local Path = require "plenary.path"
+local Path = require "plenary.path2"
 
 local tester = {}
 tester.debug = false
diff --git a/lua/telescope/utils.lua b/lua/telescope/utils.lua
index 44ab5d9b08..dae0b7e3d4 100644
--- a/lua/telescope/utils.lua
+++ b/lua/telescope/utils.lua
@@ -5,7 +5,7 @@
 --- Utilities for writing telescope pickers
 ---@brief ]]
 
-local Path = require "plenary.path"
+local Path = require "plenary.path2"
 local Job = require "plenary.job"
 
 local log = require "telescope.log"
@@ -223,7 +223,11 @@ local path_abs = function(path, opts)
   else
     cwd = vim.loop.cwd()
   end
-  return Path:new(path):make_relative(cwd)
+  local p = Path:new(path)
+  if p:is_absolute() then
+    return Path:new(path):make_relative(cwd, { walk_up = true })
+  end
+  return p.filename
 end
 
 -- IMPORTANT: This function should have been a local function as it's only used
@@ -385,7 +389,7 @@ utils.transform_path = function(opts, path)
         length = shorten.len
         exclude = shorten.exclude
       else
-        length = type(path_display["shorten"]) == "number" and path_display["shorten"]
+        length = type(path_display["shorten"]) == "number" and path_display["shorten"] or nil
       end
 
       transformed_path = path_shorten(transformed_path, length, exclude)
diff --git a/lua/tests/automated/telescope_spec.lua b/lua/tests/automated/telescope_spec.lua
index 44594dd3fa..d70c1cd45b 100644
--- a/lua/tests/automated/telescope_spec.lua
+++ b/lua/tests/automated/telescope_spec.lua
@@ -1,5 +1,5 @@
 local picker = require "telescope.pickers"
-local Path = require "plenary.path"
+local Path = require "plenary.path2"
 
 local eq = assert.are.same
 
@@ -108,7 +108,7 @@ describe("telescope", function()
     describe("fzy", function()
       local sorter = require("telescope.sorters").get_fzy_sorter()
       local function score(prompt, line)
-        line = new_path(line)
+        line = Path.is_path(line) and line.filename or new_path(line)
         return sorter:score(prompt, { ordinal = line }, function(val)
           return val
         end, function()
@@ -167,7 +167,7 @@ describe("telescope", function()
         end)
         it("prefers matches at the beginning", function()
           assert.True(score("ab", "abbb") < score("ab", "babb"))
-          assert.True(score("test", "testing") < score("test", "/testing"))
+          assert.True(score("test", "testing") < score("test", Path:new { Path.path.root(), "testing" }))
         end)
         it("prefers matches at some locations", function()
           assert.True(score("a", "/a") < score("a", "ba"))
diff --git a/lua/tests/automated/utils_spec.lua b/lua/tests/automated/utils_spec.lua
index b99a665cd3..b0e555c311 100644
--- a/lua/tests/automated/utils_spec.lua
+++ b/lua/tests/automated/utils_spec.lua
@@ -1,4 +1,4 @@
-local Path = require "plenary.path"
+local Path = require "plenary.path2"
 local utils = require "telescope.utils"
 
 local eq = assert.are.equal