diff --git a/Semantics.Paths/SemanticPath.cs b/Semantics.Paths/SemanticPath.cs
index 3d7a6bb..b41daa7 100644
--- a/Semantics.Paths/SemanticPath.cs
+++ b/Semantics.Paths/SemanticPath.cs
@@ -116,9 +116,9 @@ protected override string MakeCanonical(string input)
 		// Normalize directory separators to the current platform's preferred separator
 		canonical = canonical.Replace(Path.AltDirectorySeparatorChar, Path.DirectorySeparatorChar);
 
-		// Remove trailing directory separator (except for root paths)
+		// Remove every trailing directory separator, so "/a//" is "/a", but stop at a root path
 		string separator = new([Path.DirectorySeparatorChar]);
-		if (canonical.EndsWith(separator) && canonical.Length > separator.Length)
+		while (canonical.EndsWith(separator) && canonical.Length > separator.Length)
 		{
 			// Check if this is a Windows root path (e.g., "C:\")
 #if NET5_0_OR_GREATER
@@ -139,14 +139,16 @@ protected override string MakeCanonical(string input)
 #endif
 
 			// Only remove trailing separator if it's not a root path
-			if (!isWindowsRoot && !isUnixRoot)
+			if (isWindowsRoot || isUnixRoot)
 			{
+				break;
+			}
+
 #if NETSTANDARD2_0
-				canonical = canonical.Substring(0, canonical.Length - separator.Length);
+			canonical = canonical.Substring(0, canonical.Length - separator.Length);
 #else
-				canonical = canonical[..^separator.Length];
+			canonical = canonical[..^separator.Length];
 #endif
-			}
 		}
 
 		return canonical;
diff --git a/Semantics.Test/Paths/PathContainmentTests.cs b/Semantics.Test/Paths/PathContainmentTests.cs
index 8966c89..12e3712 100644
--- a/Semantics.Test/Paths/PathContainmentTests.cs
+++ b/Semantics.Test/Paths/PathContainmentTests.cs
@@ -97,4 +97,29 @@ public void SiblingSharingANamePrefix_IsNotAChild()
 		Assert.IsFalse(File(TestPaths.Absolute("home2.txt")).IsChildOf(home));
 		Assert.IsFalse(home.IsParentOf(Dir(TestPaths.Absolute("home2"))));
 	}
+
+	[TestMethod]
+	[DataRow(2)]
+	[DataRow(3)]
+	public void RepeatedTrailingSeparators_CanonicalizeToTheSameDirectory(int separatorCount)
+	{
+		string plain = TestPaths.Absolute("home", "user", "a");
+		AbsoluteDirectoryPath doubled = Dir(plain + new string(TestPaths.Separator, separatorCount));
+		AbsoluteDirectoryPath single = Dir(plain);
+
+		Assert.AreEqual(plain, doubled.WeakString);
+		Assert.AreEqual(single, doubled);
+		Assert.IsFalse(doubled.IsChildOf(single));
+		Assert.IsFalse(single.IsChildOf(doubled));
+		Assert.IsFalse(single.IsParentOf(doubled));
+	}
+
+	[TestMethod]
+	public void RootWithRepeatedTrailingSeparators_StaysTheRoot()
+	{
+		AbsoluteDirectoryPath root = Dir(TestPaths.Root + TestPaths.Separator + TestPaths.Separator);
+
+		Assert.AreEqual(TestPaths.Root, root.WeakString);
+		Assert.IsFalse(root.IsChildOf(Dir(TestPaths.Root)));
+	}
 }