diff --git a/lua/plenary/path.lua b/lua/plenary/path.lua
index 701679e6..0865f2e3 100644
--- a/lua/plenary/path.lua
+++ b/lua/plenary/path.lua
@@ -931,11 +931,14 @@ function Path:find_upwards(filename)
   local folder = Path:new(self)
   local root = path.root(folder:absolute())
 
-  while folder:absolute() ~= root do
+  while true do
     local p = folder:joinpath(filename)
     if p:exists() then
       return p
     end
+    if folder:absolute() == root then
+      break
+    end
     folder = folder:parent()
   end
   return nil
diff --git a/tests/plenary/path_spec.lua b/tests/plenary/path_spec.lua
index 8f916a30..0f02db04 100644
--- a/tests/plenary/path_spec.lua
+++ b/tests/plenary/path_spec.lua
@@ -721,6 +721,34 @@ SOFTWARE.]]
       assert.are.same(should, data)
     end)
   end)
+
+  describe(":find_upwards", function()
+    it("finds files that exist", function()
+      local p = Path:new(debug.getinfo(1, "S").source:sub(2))
+      local found = p:find_upwards "README.md"
+      assert.are.same(found:absolute(), Path:new("README.md"):absolute())
+    end)
+
+    it("finds files that exist at the root", function()
+      local p = Path:new(debug.getinfo(1, "S").source:sub(2))
+
+      -- Temporarily set path.root to the root of this repository
+      local root = p.path.root
+      p.path.root = function(_)
+        return p:parent():parent():parent().filename
+      end
+
+      local found = p:find_upwards "README.md"
+      assert.are.same(found:absolute(), Path:new("README.md"):absolute())
+      p.path.root = root
+    end)
+
+    it("returns nil if no file is found", function()
+      local p = Path:new(debug.getinfo(1, "S").source:sub(2))
+      local found = p:find_upwards "MISSINGNO.md"
+      assert.are.same(found, nil)
+    end)
+  end)
 end)
 
 -- function TestPath:testIsDir()