diff --git a/spec/std/path_spec.cr b/spec/std/path_spec.cr
index 9c2b69aaf45b..5c1ba284a8d5 100644
--- a/spec/std/path_spec.cr
+++ b/spec/std/path_spec.cr
@@ -191,6 +191,19 @@ describe Path do
     assert_paths("C:\\", ".", "C:\\", &.parent)
     assert_paths("C:/foo", "C:", "C:/", &.parent)
     assert_paths("C:\\foo", ".", "C:\\", &.parent)
+    assert_paths("\\\\.", ".", "\\\\.", &.parent)
+    assert_paths("\\/?", "\\", "\\/?", &.parent)
+    assert_paths("//.", "/", "//.", &.parent)
+    assert_paths("//./", "/", "//./", &.parent)
+    assert_paths("//.\\", "/", "//.\\", &.parent)
+    assert_paths("//./foo", "//.", "//./", &.parent)
+    assert_paths("//.\\foo", "/", "//.\\", &.parent)
+    assert_paths("//?/", "/", "//?/", &.parent)
+    assert_paths("//?\\", "/", "//?\\", &.parent)
+    assert_paths("//?/foo", "//?", "//?/", &.parent)
+    assert_paths("//?\\foo", "/", "//?\\", &.parent)
+    assert_paths("\\\\?/", ".", "\\\\?/", &.parent)
+    assert_paths("\\\\?\\", ".", "\\\\?\\", &.parent)
     assert_paths("/foo/C:/bar", "/foo/C:", "/foo/C:", &.parent)
     assert_paths("//some/share", "//some", "//some/share", &.parent)
     assert_paths("//some/share/", "//some", "//some/share/", &.parent)
@@ -241,6 +254,19 @@ describe Path do
     assert_paths("C:\\folder", ["."], ["C:\\"], &.parents)
     assert_paths("C:\\\\folder", ["."], ["C:\\\\"], &.parents)
     assert_paths("C:\\.", ["."], ["C:\\"], &.parents)
+    assert_paths("\\\\.", ["."], [] of String, &.parents)
+    assert_paths("\\/?", [".", "\\"], [] of String, &.parents)
+    assert_paths("//.", ["//"], [] of String, &.parents)
+    assert_paths("//./", ["//"], [] of String, &.parents)
+    assert_paths("//.\\", ["//"], [] of String, &.parents)
+    assert_paths("//./foo", ["//", "//."], ["//./"], &.parents)
+    assert_paths("//.\\foo", ["//"], ["//.\\"], &.parents)
+    assert_paths("//?/", ["//"], [] of String, &.parents)
+    assert_paths("//?\\", ["//"], [] of String, &.parents)
+    assert_paths("//?/foo", ["//", "//?"], ["//?/"], &.parents)
+    assert_paths("//?\\foo", ["//"], ["//?\\"], &.parents)
+    assert_paths("\\\\?/", ["."], [] of String, &.parents)
+    assert_paths("\\\\?\\", ["."], [] of String, &.parents)
     assert_paths("//some/share", ["//", "//some"], [] of String, &.parents)
     assert_paths("//some/share/", ["//", "//some"], [] of String, &.parents)
     assert_paths("//some/share/a", ["//", "//some", "//some/share"], ["//some/share/"], &.parents)
@@ -264,6 +290,21 @@ describe Path do
     assert_paths_raw("C:", ".", "C:", &.dirname)
     assert_paths_raw("C:/", ".", "C:/", &.dirname)
     assert_paths_raw("C:\\", ".", "C:\\", &.dirname)
+    assert_paths_raw("C:/foo", "C:", "C:/", &.dirname)
+    assert_paths_raw("C:\\foo", ".", "C:\\", &.dirname)
+    assert_paths_raw("\\\\.", ".", "\\\\.", &.dirname)
+    assert_paths_raw("\\/?", "\\", "\\/?", &.dirname)
+    assert_paths_raw("//.", "/", "//.", &.dirname)
+    assert_paths_raw("//./", "/", "//./", &.dirname)
+    assert_paths_raw("//.\\", "/", "//.\\", &.dirname)
+    assert_paths_raw("//./foo", "//.", "//./", &.dirname)
+    assert_paths_raw("//.\\foo", "/", "//.\\", &.dirname)
+    assert_paths_raw("//?/", "/", "//?/", &.dirname)
+    assert_paths_raw("//?\\", "/", "//?\\", &.dirname)
+    assert_paths_raw("//?/foo", "//?", "//?/", &.dirname)
+    assert_paths_raw("//?\\foo", "/", "//?\\", &.dirname)
+    assert_paths_raw("\\\\?/", ".", "\\\\?/", &.dirname)
+    assert_paths_raw("\\\\?\\", ".", "\\\\?\\", &.dirname)
     assert_paths_raw("//some/share", "//some", "//some/share", &.dirname)
     assert_paths_raw("//some/share/", "//some", "//some/share/", &.dirname)
     assert_paths_raw("//some/share/a", "//some/share", "//some/share/", &.dirname)
@@ -355,6 +396,14 @@ describe Path do
     it_iterates_parts("C:\\folder", ["C:\\folder"], ["C:\\", "folder"])
     it_iterates_parts("C:\\\\folder", ["C:\\\\folder"], ["C:\\\\", "folder"])
     it_iterates_parts("C:\\.", ["C:\\."], ["C:\\", "."])
+    it_iterates_parts("//.", ["//", "."], ["//."])
+    it_iterates_parts("//?", ["//", "?"], ["//?"])
+    it_iterates_parts("\\\\.\\", ["\\\\.\\"], ["\\\\.\\"])
+    it_iterates_parts("\\\\?\\", ["\\\\?\\"], ["\\\\?\\"])
+    it_iterates_parts("\\\\.\\foo", ["\\\\.\\foo"], ["\\\\.\\", "foo"])
+    it_iterates_parts("\\\\?\\foo", ["\\\\?\\foo"], ["\\\\?\\", "foo"])
+    it_iterates_parts("\\\\.\\foo\\bar", ["\\\\.\\foo\\bar"], ["\\\\.\\", "foo", "bar"])
+    it_iterates_parts("\\\\?\\foo\\bar", ["\\\\?\\foo\\bar"], ["\\\\?\\", "foo", "bar"])
   end
 
   describe "#extension" do
@@ -386,6 +435,7 @@ describe Path do
     assert_paths_raw(".\\foo", false, &.absolute?)
     assert_paths_raw("~\\foo", false, &.absolute?)
     assert_paths_raw("C:", false, &.absolute?)
+    assert_paths_raw("C:foo", false, &.absolute?)
 
     assert_paths_raw("C:\\foo", false, true, &.absolute?)
     assert_paths_raw("C:/foo/bar", false, true, &.absolute?)
@@ -398,6 +448,13 @@ describe Path do
     assert_paths_raw("\\\\some\\share", false, false, &.absolute?)
     assert_paths_raw("//some/share/", true, true, &.absolute?)
     assert_paths_raw("\\\\some\\share\\", false, true, &.absolute?)
+
+    assert_paths_raw("//.", true, false, &.absolute?)
+    assert_paths_raw("\\\\?", false, false, &.absolute?)
+    assert_paths_raw("//./foo", true, true, &.absolute?)
+    assert_paths_raw("\\\\.\\foo", false, true, &.absolute?)
+    assert_paths_raw("//?/foo", true, true, &.absolute?)
+    assert_paths_raw("\\\\?\\foo", false, true, &.absolute?)
   end
 
   describe "#drive" do
@@ -416,6 +473,12 @@ describe Path do
     assert_paths("\\\\some\\share\\foo", nil, "\\\\some\\share", &.drive)
     assert_paths("\\\\\\not-a\\share", nil, nil, &.drive)
     assert_paths("\\\\not-a\\\\share", nil, nil, &.drive)
+    assert_paths("\\\\?\\", nil, "\\\\?", &.drive)
+    assert_paths("\\\\.\\", nil, "\\\\.", &.drive)
+    assert_paths("//?/", nil, "//?", &.drive)
+    assert_paths("//./", nil, "//.", &.drive)
+    assert_paths("//?", nil, "//?", &.drive)
+    assert_paths("//.", nil, "//.", &.drive)
 
     assert_paths("\\\\some$\\share\\", nil, "\\\\some$\\share", &.drive)
     assert_paths("\\\\%10%20\\share\\", nil, "\\\\%10%20\\share", &.drive)
@@ -435,6 +498,12 @@ describe Path do
     assert_paths("\\\\some\\share", nil, &.root)
     assert_paths("//some/share/", "/", "/", &.root)
     assert_paths("\\\\some\\share\\", nil, "\\", &.root)
+    assert_paths("\\\\?\\", nil, "\\", &.root)
+    assert_paths("\\\\.\\", nil, "\\", &.root)
+    assert_paths("//?/", "/", "/", &.root)
+    assert_paths("//./", "/", "/", &.root)
+    assert_paths("//?", "/", nil, &.root)
+    assert_paths("//.", "/", nil, &.root)
   end
 
   describe "#anchor" do
@@ -447,6 +516,12 @@ describe Path do
     assert_paths("//some/share/", "/", "//some/share/", &.anchor)
     assert_paths("\\\\some\\share", nil, "\\\\some\\share", &.anchor)
     assert_paths("\\\\some\\share\\", nil, "\\\\some\\share\\", &.anchor)
+    assert_paths("\\\\?\\", nil, "\\\\?\\", &.anchor)
+    assert_paths("\\\\.\\", nil, "\\\\.\\", &.anchor)
+    assert_paths("//?/", "/", "//?/", &.anchor)
+    assert_paths("//./", "/", "//./", &.anchor)
+    assert_paths("//?", "/", "//?", &.anchor)
+    assert_paths("//.", "/", "//.", &.anchor)
   end
 
   describe "#normalize" do
@@ -566,6 +641,14 @@ describe Path do
       it_normalizes_path("C:\\foo", "C:\\foo")
       it_normalizes_path("C:/foo", "C:/foo", "C:\\foo")
     end
+
+    describe "windows local device paths" do
+      it_normalizes_path("\\\\.\\C:\\..\\D:\\foo\\.\\bar", windows: "\\\\.\\D:\\foo\\bar")
+      it_normalizes_path("//./c:/", "/c:", windows: "\\\\.\\c:\\")
+      it_normalizes_path("//?/c:", "/?/c:", windows: "\\\\?\\c:")
+      it_normalizes_path("\\/.\\c:/\\", windows: "\\\\.\\c:\\")
+      it_normalizes_path("\\\\?\\c:\\")
+    end
   end
 
   describe "#join" do
diff --git a/src/path.cr b/src/path.cr
index 1063cdacc84f..21daa97b14ed 100644
--- a/src/path.cr
+++ b/src/path.cr
@@ -45,7 +45,7 @@ require "crystal/system/path"
 # * POSIX paths are generally case-sensitive, Windows paths case-insensitive
 #   (see `#<=>`).
 # * A POSIX path is absolute if it begins with a forward slash (`/`). A Windows path
-#   is absolute if it starts with a drive letter and root (`C:\`).
+#   is absolute if it starts with both a drive and a root (see `#absolute?`).
 #
 # ```
 # Path.posix("/foo/./bar").normalize   # => Path.posix("/foo/bar")
@@ -221,7 +221,7 @@ struct Path
     when 0 # Path only consists of separators
       String.new(slice[0, 1])
     when 1 # Path has no parent (ex. "hello/", "C:/", "crystal")
-      return anchor.to_s if windows? && windows_drive?
+      return anchor.to_s if windows? && (windows_drive? || dos_local_device_path?)
       "."
     else # Path has a parent (ex. "a/a", "/home/user//", "C://Users/mmm", "\\wsl.localhost\Debian")
       if windows? && (anchor = self.anchor) && pos < anchor.to_s.bytesize
@@ -407,7 +407,11 @@ struct Path
   #
   # If the path turns to be empty, the current directory (`"."`) is returned.
   #
-  # The returned path ends in a slash only if it is the root (`"/"`, `\`, or `C:\`).
+  # The returned path ends in a slash if it is the root (`"/"`, `\`, or `C:\`),
+  # or if this path is a Windows local device path that also ends in a slash.
+  # This trailing slash is significant; `\\.\C:` refers to the _volume_ `C:`, on
+  # which most I/O functions fail, whereas `\\.\C:\` refers to the root
+  # _directory_ of said volume.
   #
   # See also Rob Pike: *[Lexical File Names in Plan 9 or Getting Dot-Dot Right](https://9p.io/sys/doc/lexnames.html)*
   def normalize(*, remove_final_separator : Bool = true) : Path
@@ -417,7 +421,7 @@ struct Path
     reader = Char::Reader.new(@name)
     dotdot = 0
     separators = self.separators
-    add_separator_at_end = !remove_final_separator && ends_with_separator?
+    add_separator_at_end = (!remove_final_separator || (windows? && dos_local_device_path?)) && ends_with_separator?
 
     new_name = String.build do |str|
       if drive
@@ -969,6 +973,11 @@ struct Path
   # Returns `nil` if `self` cannot be expressed as relative to *base* or if
   # knowing the current working directory would be necessary to resolve it. The
   # latter can be avoided by expanding the paths first.
+  #
+  # For Windows paths, the drive and the root must be identical; relative paths
+  # between different path types are not supported, even if they would resolve
+  # to the same roots (e.g. `\\.\C:\foo` and `C:\foo` are not equivalent, nor
+  # are `\\?\UNC\server\share\foo` and `\\server\share\foo`).
   def relative_to?(base : Path) : Path?
     base_anchor = base.anchor
     target_anchor = self.anchor
@@ -1118,9 +1127,13 @@ struct Path
   # ```
   # Path.windows("C:\\Program Files").drive       # => Path.windows("C:")
   # Path.windows("\\\\host\\share\\folder").drive # => Path.windows("\\\\host\\share")
+  # Path.windows("\\\\.\\NUL").drive              # => Path.windows("\\\\.")
+  # Path.windows("//?").drive                     # => Path.windows("//?")
   # ```
   #
-  # NOTE: Drives are only available for Windows paths. It can either be a drive letter (`C:`) or a UNC share (`\\host\share`).
+  # NOTE: Drives are only available for Windows paths. It can be a drive letter
+  # (`C:`), a UNC share (`\\host\share`), or a root local device path (`\\.`,
+  # `\\?`).
   def drive : Path?
     drive_end, _ = drive_and_root_indices
 
@@ -1139,6 +1152,8 @@ struct Path
   # Path.windows("C:Program Files").root         # => nil
   # Path.windows("C:\\Program Files").root       # => Path.windows("\\")
   # Path.windows("\\\\host\\share\\folder").root # => Path.windows("\\")
+  # Path.windows("//./NUL").root                 # => Path.windows("/")
+  # Path.windows("\\\\?").root                   # => nil
   # ```
   def root : Path?
     drive_end, root_end = drive_and_root_indices
@@ -1157,6 +1172,8 @@ struct Path
   # Path.windows("C:Program Files").anchor         # => Path.windows("C:")
   # Path.windows("C:\\Program Files").anchor       # => Path.windows("C:\\")
   # Path.windows("\\\\host\\share\\folder").anchor # => Path.windows("\\\\host\\share\\")
+  # Path.windows("\\\\.\\NUL").anchor              # => Path.windows("\\\\.\\")
+  # Path.windows("//?").anchor                     # => Path.windows("//?")
   # ```
   def anchor : Path?
     drive_end, root_end = drive_and_root_indices
@@ -1191,6 +1208,12 @@ struct Path
         else
           {2, nil}
         end
+      elsif dos_local_device_path?
+        if separators.includes?(@name.byte_at?(3).try(&.chr))
+          {3, 4}
+        else
+          {3, nil}
+        end
       elsif unc_share = unc_share?
         unc_share
       elsif starts_with_separator?
@@ -1205,6 +1228,14 @@ struct Path
     end
   end
 
+  private def dos_local_device_path?
+    # `//./`, `\\?` etc.
+    @name.size >= 3 &&
+      separators.includes?(@name.to_unsafe[0].unsafe_chr) &&
+      separators.includes?(@name.to_unsafe[1].unsafe_chr) &&
+      {'.', '?'}.includes?(@name.to_unsafe[2].unsafe_chr)
+  end
+
   private def unc_share?
     # Test for UNC share
     # path: //share/share
@@ -1280,14 +1311,19 @@ struct Path
   # Returns `true` if this path is absolute.
   #
   # A POSIX path is absolute if it begins with a forward slash (`/`).
-  # A Windows path is absolute if it begins with a drive letter and root (`C:\`)
-  # or with a UNC share (`\\server\share\`).
+  #
+  # A Windows path is absolute if it begins with a drive letter (`C:`), a UNC
+  # share (`\\server\share`), or a root local device path (`\\.`, `\\?`), which
+  # is then followed by a root path separator. Drive-relative paths (`C:foo`),
+  # rooted paths (`\foo`), and root local device paths (`\\.`) are not absolute.
   def absolute? : Bool
     separators = self.separators
     if windows?
       first_is_separator = false
       starts_with_double_separator = false
       found_share_name = false
+      found_dot_or_question_mark = false
+
       @name.each_char_with_index do |char, index|
         case index
         when 0
@@ -1303,14 +1339,21 @@ struct Path
             return false unless char == ':'
           end
         else
-          if separators.includes?(char)
+          case char
+          when .in?(separators)
             if index == 2
               return !starts_with_double_separator && !found_share_name
+            elsif index == 3 && found_dot_or_question_mark
+              return true
             elsif found_share_name
               return true
             else
               found_share_name = true
             end
+          when '.', '?'
+            if index == 2
+              found_dot_or_question_mark = true
+            end
           end
         end
       end