diff --git a/lib/std/io/path.c3 b/lib/std/io/path.c3
index e729b018a..d98251018 100644
--- a/lib/std/io/path.c3
+++ b/lib/std/io/path.c3
@@ -399,6 +399,19 @@ fn Path? Path.parent(self)
 	{
 		if (is_separator(c, self.env))
 		{
+			if (i == 0) return { self.path_string[..0], self.env, null };
+			if (self.env == WIN32 && i > 1)
+			{
+				if (try volume_len = volume_name_len(self.path_string, WIN32))
+				{
+					// Handle C:\foo
+					if (volume_len == i)
+					{
+						if (i + 1 == self.path_string.len) return NO_PARENT?;
+						return { self.path_string[:i + 1], WIN32, null };
+					}
+				}
+			}
 			return { self.path_string[:i], self.env, null };
 		}
 	}
diff --git a/releasenotes.md b/releasenotes.md
index 066900143..48d25ab1a 100644
--- a/releasenotes.md
+++ b/releasenotes.md
@@ -18,6 +18,7 @@
 - Error message with hashmap shows "mangled" name instead of original #2562.
 - Passing a compile time type implicitly converted to a typeid would crash instead of producing an error. #2568
 - Compiler assert with const enum based on vector #2566
+- Fix to `Path` handling `c:\foo` and `\home` parent. #2569
 
 ### Stdlib changes
 
diff --git a/test/unit/stdlib/io/path.c3 b/test/unit/stdlib/io/path.c3
index d5c7503b3..e77d2b5ec 100644
--- a/test/unit/stdlib/io/path.c3
+++ b/test/unit/stdlib/io/path.c3
@@ -34,6 +34,13 @@ fn void test_parent()
 	p = path::new(mem, "/a/b/c", path_env: PathEnv.WIN32)!!;
 	assert(p.parent().str_view()!! == `\a\b`);
 	p.free();
+	p = path::new(mem, "/a/", path_env: PathEnv.POSIX)!!;
+	assert(p.parent().str_view()!! == "/");
+	p.free();
+	p = path::new(mem, `C:\foo`, path_env: WIN32)!!;
+    assert(p.parent().str_view()!! == `C:\`);
+    assert(@catch(p.parent().parent()));
+    p.free();
 }
 
 fn void test_path_normalized() => mem::@scoped(tmem)