diff --git a/CHANGELOG.md b/CHANGELOG.md
index 7bef8de5..67495819 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -7,6 +7,8 @@ deprecation policy.
 see [CONTRIBUTING.md](CONTRIBUTING.md#release-instructions-for-a-new-version) for release instructions
 
 ## 1.14.0 (unreleased)
+ - fix(path): make `path.expanduser` more sturdy
+   [#469](https://github.com/lunarmodules/Penlight/pull/469)
  - feat(func): extend `compose` to support N functions
    [#448](https://github.com/lunarmodules/Penlight/pull/448)
  - fix(utils) `nil` values in `utils.choose(cond, val1, val2)`
diff --git a/lua/pl/path.lua b/lua/pl/path.lua
index 1e044e11..600bf057 100644
--- a/lua/pl/path.lua
+++ b/lua/pl/path.lua
@@ -493,17 +493,35 @@ end
 -- In windows, if HOME isn't set, then USERPROFILE is used in preference to
 -- HOMEDRIVE HOMEPATH. This is guaranteed to be writeable on all versions of Windows.
 -- @string P A file path
+-- @treturn[1] string The file path with the `~` prefix substituted, or the input path if it had no prefix.
+-- @treturn[2] nil
+-- @treturn[2] string Error message if the environment variables were unavailable.
 function path.expanduser(P)
     assert_string(1,P)
-    if at(P,1) == '~' then
-        local home = getenv('HOME')
-        if not home then -- has to be Windows
-            home = getenv 'USERPROFILE' or (getenv 'HOMEDRIVE' .. getenv 'HOMEPATH')
-        end
-        return home..sub(P,2)
-    else
+    if P:sub(1,1) ~= '~' then
         return P
     end
+
+    local home = getenv('HOME')
+    if (not home) and (not path.is_windows) then
+        -- no more options to try on Nix
+        return nil, "failed to expand '~' (HOME not set)"
+    end
+
+    if (not home) then
+        -- try alternatives on Windows
+        home = getenv 'USERPROFILE'
+        if not home then
+            local hd = getenv 'HOMEDRIVE'
+            local hp = getenv 'HOMEPATH'
+            if not (hd and hp) then
+              return nil, "failed to expand '~' (HOME, USERPROFILE, and HOMEDRIVE and/or HOMEPATH not set)"
+            end
+            home = hd..hp
+        end
+    end
+
+    return home..sub(P,2)
 end
 
 
diff --git a/spec/path_spec.lua b/spec/path_spec.lua
new file mode 100644
index 00000000..7f18f29d
--- /dev/null
+++ b/spec/path_spec.lua
@@ -0,0 +1,106 @@
+
+-- conditional it/pending blocks per platform
+local function nix_it(desc, ...)
+  if package.config:sub(1,1) == "\\" then
+    pending("Skip test on Windows: " .. desc, ...)
+  else
+    it(desc, ...)
+  end
+end
+local function win_it(desc, ...)
+  if package.config:sub(1,1) == "\\" then
+    it(desc, ...)
+  else
+    pending("Skip test on Unix: " .. desc, ...)
+  end
+end
+
+
+
+describe("pl.path", function()
+
+  local path
+  local mock_envs
+  local old_get_env
+
+  before_each(function()
+    mock_envs = {}
+    old_get_env = os.getenv
+    os.getenv = function(name)      -- luacheck: ignore
+      return mock_envs[name]
+    end
+    package.loaded["pl.path"] = nil
+    path = require "pl.path"
+  end)
+
+  after_each(function()
+    package.loaded["pl.path"] = nil
+    os.getenv = old_get_env         -- luacheck: ignore
+  end)
+
+
+
+  describe("expanduser()", function()
+
+    it("should expand ~ to the user's home directory", function()
+      mock_envs = {
+        HOME = "/home/user",
+      }
+      assert.equal("/home/user/file", path.expanduser("~/file"))
+    end)
+
+
+    nix_it("returns an error if expansion fails: HOME not set", function()
+      mock_envs = {}
+      assert.same(
+        { nil, "failed to expand '~' (HOME not set)" },
+        { path.expanduser("~/file")}
+      )
+    end)
+
+
+    win_it("returns an error if expansion fails: all Windows vars", function()
+      mock_envs = {}
+      assert.same(
+        { nil, "failed to expand '~' (HOME, USERPROFILE, and HOMEDRIVE and/or HOMEPATH not set)" },
+        { path.expanduser("~/file")}
+      )
+    end)
+
+
+    win_it("HOME is first in line", function()
+      mock_envs = {
+        HOME = "\\home\\user1",
+        USERPROFILE = "\\home\\user2",
+        HOMEDRIVE = "C:",
+        HOMEPATH = "\\home\\user3",
+      }
+      assert.equal("\\home\\user1\\file", path.expanduser("~\\file"))
+    end)
+
+
+    win_it("USERPROFILE is second in line", function()
+      mock_envs = {
+        --HOME = "\\home\\user1",
+        USERPROFILE = "\\home\\user2",
+        HOMEDRIVE = "C:",
+        HOMEPATH = "\\home\\user3",
+      }
+      assert.equal("\\home\\user2\\file", path.expanduser("~\\file"))
+    end)
+
+
+    win_it("HOMEDRIVE/PATH is third in line", function()
+      mock_envs = {
+        -- HOME = "\\home\\user1",
+        -- USERPROFILE = "\\home\\user2",
+        HOMEDRIVE = "C:",
+        HOMEPATH = "\\home\\user3",
+      }
+      assert.equal("C:\\home\\user3\\file", path.expanduser("~\\file"))
+    end)
+
+  end)
+
+end)
+
diff --git a/tests/test-path.lua b/tests/test-path.lua
index 2368b388..8023270a 100644
--- a/tests/test-path.lua
+++ b/tests/test-path.lua
@@ -179,8 +179,6 @@ do  --  path.relpath
 end
 
 
--- TODO: path.expanduser
-
 -- TODO: path.tmpname