diff --git a/Semantics.Paths/Implementations/AbsoluteDirectoryPath.cs b/Semantics.Paths/Implementations/AbsoluteDirectoryPath.cs
index 72a123b8..6e5e7f80 100644
--- a/Semantics.Paths/Implementations/AbsoluteDirectoryPath.cs
+++ b/Semantics.Paths/Implementations/AbsoluteDirectoryPath.cs
@@ -18,13 +18,31 @@ public sealed record AbsoluteDirectoryPath : SemanticDirectoryPath<AbsoluteDirec
 	/// <summary>
 	/// Gets the parent directory of this absolute directory path.
 	/// </summary>
-	/// <value>An <see cref="AbsoluteDirectoryPath"/> representing the parent directory, or an empty path if this is a root directory.</value>
+	/// <value>
+	/// An <see cref="AbsoluteDirectoryPath"/> representing the parent directory, or this same path when it is a
+	/// root directory and therefore has no parent above it.
+	/// </value>
+	/// <remarks>
+	/// A root is its own parent, matching how the filesystem resolves <c>/..</c> to <c>/</c> and <c>C:\..</c> to
+	/// <c>C:\</c>. This keeps every value this property returns a usable absolute directory rather than an empty
+	/// path, which silently reads as "no contents" when passed to the filesystem. Use <see cref="IsRoot"/>, or
+	/// compare the parent against this path, to detect that walking upwards has finished.
+	/// </remarks>
 	public AbsoluteDirectoryPath Parent
 	{
 		get
 		{
-			return _cachedParent ??= Create<AbsoluteDirectoryPath>(
-				InternedPathStrings.InternIfCommon(Path.GetDirectoryName(WeakString) ?? InternedPathStrings.Empty));
+			if (_cachedParent is not null)
+			{
+				return _cachedParent;
+			}
+
+			string? parent = Path.GetDirectoryName(WeakString);
+			_cachedParent = string.IsNullOrEmpty(parent)
+				? this
+				: Create<AbsoluteDirectoryPath>(InternedPathStrings.InternIfCommon(parent));
+
+			return _cachedParent;
 		}
 	}
 
diff --git a/Semantics.Test/Paths/AbsoluteDirectoryPathParentTests.cs b/Semantics.Test/Paths/AbsoluteDirectoryPathParentTests.cs
new file mode 100644
index 00000000..6c51381e
--- /dev/null
+++ b/Semantics.Test/Paths/AbsoluteDirectoryPathParentTests.cs
@@ -0,0 +1,119 @@
+// Copyright (c) ktsu.dev
+// All rights reserved.
+// Licensed under the MIT license.
+
+namespace ktsu.Semantics.Test.Paths;
+
+using System;
+using System.Collections.Generic;
+using System.IO;
+using System.Linq;
+using ktsu.Semantics.Paths;
+using Microsoft.VisualStudio.TestTools.UnitTesting;
+
+/// <summary>
+/// Tests for walking upwards from an <see cref="AbsoluteDirectoryPath"/>.
+/// </summary>
+[TestClass]
+public class AbsoluteDirectoryPathParentTests
+{
+	private static AbsoluteDirectoryPath Dir(string path) => AbsoluteDirectoryPath.Create<AbsoluteDirectoryPath>(path);
+
+	private static string Nested => OperatingSystem.IsWindows() ? @"C:\Users\user\Documents" : "/home/user/Documents";
+
+	private static string Middle => OperatingSystem.IsWindows() ? @"C:\Users\user" : "/home/user";
+
+	private static string BelowRoot => OperatingSystem.IsWindows() ? @"C:\Users" : "/home";
+
+	private static string Root => OperatingSystem.IsWindows() ? @"C:\" : "/";
+
+	[TestMethod]
+	public void Parent_ReturnsTheContainingDirectory()
+	{
+		Assert.AreEqual(Middle, Dir(Nested).Parent.WeakString);
+		Assert.AreEqual(BelowRoot, Dir(Middle).Parent.WeakString);
+		Assert.AreEqual(Root, Dir(BelowRoot).Parent.WeakString);
+	}
+
+	[TestMethod]
+	public void Parent_OfRoot_ReturnsTheRootItself()
+	{
+		AbsoluteDirectoryPath root = Dir(Root);
+
+		Assert.IsTrue(root.IsRoot, $"'{root}' should be a root.");
+		Assert.AreEqual(root, root.Parent);
+	}
+
+	[TestMethod]
+	public void Parent_OfUncShareRoot_ReturnsTheShareItself()
+	{
+		if (!OperatingSystem.IsWindows())
+		{
+			Assert.Inconclusive("UNC paths are Windows-only.");
+			return;
+		}
+
+		Assert.AreEqual(@"\\server\share", Dir(@"\\server\share\folder").Parent.WeakString);
+
+		AbsoluteDirectoryPath share = Dir(@"\\server\share");
+		Assert.AreEqual(share, share.Parent);
+	}
+
+	/// <summary>
+	/// Regression test for ktsu-dev/ImGuiApp#281. A root used to report an empty parent, which still passes
+	/// <see cref="AbsoluteDirectoryPath"/> validation but is not a location: passed to the filesystem it reads
+	/// as "no contents" rather than failing, so callers walking upwards silently landed nowhere.
+	/// </summary>
+	[TestMethod]
+	public void Parent_IsAlwaysAUsableAbsolutePath()
+	{
+		AbsoluteDirectoryPath current = Dir(Environment.CurrentDirectory);
+		int stepsPastRoot = current.Depth + 2;
+
+		for (int step = 0; step < stepsPastRoot; step++)
+		{
+			AbsoluteDirectoryPath parent = current.Parent;
+
+			Assert.IsFalse(string.IsNullOrEmpty(parent.WeakString), $"The parent of '{current}' should not be empty.");
+			Assert.IsTrue(
+				Path.IsPathFullyQualified(parent.WeakString),
+				$"The parent of '{current}' should be fully qualified, but was '{parent}'.");
+
+			current = parent;
+		}
+
+		Assert.IsTrue(current.IsRoot, $"Walking upwards should settle on a root, but settled on '{current}'.");
+	}
+
+	[TestMethod]
+	public void Parent_OfRoot_IsAFixedPointSoWalkingUpwardsTerminates()
+	{
+		AbsoluteDirectoryPath current = Dir(Environment.CurrentDirectory);
+		int steps = 0;
+
+		while (!current.IsRoot)
+		{
+			current = current.Parent;
+			Assert.IsLessThan(1000, ++steps, "Walking upwards should terminate at a root.");
+		}
+
+		Assert.AreEqual(current, current.Parent);
+	}
+
+	[TestMethod]
+	public void GetAncestors_EndsAtTheRootWithoutRepeatingIt()
+	{
+		List<AbsoluteDirectoryPath> ancestors = [.. Dir(Nested).GetAncestors()];
+
+		CollectionAssert.AreEqual(
+			new List<AbsoluteDirectoryPath> { Dir(Middle), Dir(BelowRoot), Dir(Root) },
+			ancestors,
+			$"Expected the chain up to the root, got [{string.Join(", ", ancestors.Select(a => a.WeakString))}].");
+	}
+
+	[TestMethod]
+	public void GetAncestors_OfRoot_IsEmpty()
+	{
+		Assert.IsEmpty(Dir(Root).GetAncestors());
+	}
+}