diff --git a/Semantics.Paths/Implementations/RelativeDirectoryPath.cs b/Semantics.Paths/Implementations/RelativeDirectoryPath.cs
index 664b2d2..2ab0e32 100644
--- a/Semantics.Paths/Implementations/RelativeDirectoryPath.cs
+++ b/Semantics.Paths/Implementations/RelativeDirectoryPath.cs
@@ -2,11 +2,9 @@
 
 namespace ktsu.Semantics.Paths;
 
+using System.Collections.Generic;
 using System.Diagnostics.CodeAnalysis;
 using System.IO;
-#if !NET5_0_OR_GREATER
-using System.Runtime.InteropServices;
-#endif
 
 /// <summary>
 /// Represents a relative directory path
@@ -209,18 +207,26 @@ public RelativeDirectoryPath AsRelative(AbsoluteDirectoryPath baseDirectory)
 			return this;
 		}
 
-		// Use Path.GetFullPath with a dummy base to normalize relative paths
-#if NET5_0_OR_GREATER
-		string dummyBase = OperatingSystem.IsWindows() ? "C:\\" : "/";
-#else
-		string dummyBase = RuntimeInformation.IsOSPlatform(OSPlatform.Windows) ? "C:\\" : "/";
-#endif
-		string fullPath = Path.GetFullPath(Path.Combine(dummyBase, path));
-#if NETSTANDARD2_0
-		string normalized = PathPolyfill.GetRelativePath(dummyBase, fullPath);
-#else
-		string normalized = Path.GetRelativePath(dummyBase, fullPath);
-#endif
+		// Resolve segments lexically. Resolving against a dummy root would discard every ".." that
+		// climbs above the starting point, changing which directory the path names.
+		List<string> segments = [];
+		foreach (string segment in path.Split(['/', '\\'], StringSplitOptions.RemoveEmptyEntries))
+		{
+			if (segment == ".")
+			{
+				continue;
+			}
+
+			if (segment == ".." && segments.Count > 0 && segments[^1] != "..")
+			{
+				segments.RemoveAt(segments.Count - 1);
+				continue;
+			}
+
+			segments.Add(segment);
+		}
+
+		string normalized = segments.Count == 0 ? "." : string.Join(Path.DirectorySeparatorChar.ToString(), segments);
 
 		return Create<RelativeDirectoryPath>(normalized);
 	}
diff --git a/Semantics.Test/Paths/PathUtilityTests.cs b/Semantics.Test/Paths/PathUtilityTests.cs
index 6829637..2382aaf 100644
--- a/Semantics.Test/Paths/PathUtilityTests.cs
+++ b/Semantics.Test/Paths/PathUtilityTests.cs
@@ -178,8 +178,22 @@ public void Normalize_WithOnlyDots_ResolvesCorrectly()
 
 		RelativeDirectoryPath normalized = dotPath.Normalize();
 
-		Assert.IsNotNull(normalized);
-		Assert.Contains("folder", normalized.WeakString);
+		Assert.AreEqual(TestPaths.Relative("..", "folder"), normalized.WeakString);
+	}
+
+	[TestMethod]
+	[DataRow(new[] { "..", "sibling" }, new[] { "..", "sibling" })]
+	[DataRow(new[] { "a", "..", "..", "b" }, new[] { "..", "b" })]
+	[DataRow(new[] { "..", "..", "x", "y" }, new[] { "..", "..", "x", "y" })]
+	[DataRow(new[] { "a", ".", "b", "..", "c" }, new[] { "a", "c" })]
+	[DataRow(new[] { "a", ".." }, new[] { "." })]
+	public void Normalize_KeepsParentSegmentsThatClimbAboveTheStart(string[] input, string[] expected)
+	{
+		RelativeDirectoryPath path = RelativeDirectoryPath.Create<RelativeDirectoryPath>(TestPaths.Relative(input));
+
+		RelativeDirectoryPath normalized = path.Normalize();
+
+		Assert.AreEqual(TestPaths.Relative(expected), normalized.WeakString);
 	}
 
 	[TestMethod]