diff --git a/extensions/git/src/test/git.test.ts b/extensions/git/src/test/git.test.ts
index b9c08fb907fa0..51042a9a845aa 100644
--- a/extensions/git/src/test/git.test.ts
+++ b/extensions/git/src/test/git.test.ts
@@ -6,7 +6,7 @@
 import 'mocha';
 import { GitStatusParser, parseGitCommits, parseGitmodules, parseLsTree, parseLsFiles, parseGitRemotes, parseCoAuthors } from '../git';
 import * as assert from 'assert';
-import { splitInChunks } from '../util';
+import { splitInChunks, isDescendant, pathEquals, relativePath } from '../util';
 
 suite('git', () => {
 	suite('GitStatusParser', () => {
@@ -644,6 +644,90 @@ suite('git', () => {
 		});
 	});
 
+	suite('isDescendant', () => {
+		test('regular paths (posix)', function () {
+			if (process.platform !== 'win32') {
+				assert.strictEqual(isDescendant('/foo', '/foo/bar'), true);
+				assert.strictEqual(isDescendant('/foo/', '/foo/bar'), true);
+				assert.strictEqual(isDescendant('/foo', '/bar/baz'), false);
+				assert.strictEqual(isDescendant('/foo', '/foo'), true);
+			}
+		});
+
+		test('root path "/" (chroot environments)', function () {
+			if (process.platform !== 'win32') {
+				assert.strictEqual(isDescendant('/', '/foo'), true);
+				assert.strictEqual(isDescendant('/', '/foo/bar'), true);
+				assert.strictEqual(isDescendant('/', '/'), true);
+			}
+		});
+
+		test('regular paths (win32)', function () {
+			if (process.platform === 'win32') {
+				assert.strictEqual(isDescendant('C:\\foo', 'C:\\foo\\bar'), true);
+				assert.strictEqual(isDescendant('C:\\foo\\', 'C:\\foo\\bar'), true);
+				assert.strictEqual(isDescendant('C:\\foo', 'C:\\bar\\baz'), false);
+				assert.strictEqual(isDescendant('C:\\foo', 'C:\\foo'), true);
+			}
+		});
+
+		test('drive root "C:\\" (win32)', function () {
+			if (process.platform === 'win32') {
+				assert.strictEqual(isDescendant('C:\\', 'C:\\foo'), true);
+				assert.strictEqual(isDescendant('C:\\', 'C:\\foo\\bar'), true);
+				assert.strictEqual(isDescendant('C:\\', 'C:\\'), true);
+			}
+		});
+	});
+
+	suite('pathEquals', () => {
+		test('regular paths (posix)', function () {
+			if (process.platform !== 'win32') {
+				assert.strictEqual(pathEquals('/foo', '/foo'), true);
+				assert.strictEqual(pathEquals('/foo/', '/foo'), true);
+				assert.strictEqual(pathEquals('/foo', '/bar'), false);
+			}
+		});
+
+		test('root path "/"', function () {
+			if (process.platform !== 'win32') {
+				assert.strictEqual(pathEquals('/', '/'), true);
+				assert.strictEqual(pathEquals('/', '/foo'), false);
+			}
+		});
+
+		test('regular paths (win32)', function () {
+			if (process.platform === 'win32') {
+				assert.strictEqual(pathEquals('C:\\foo', 'C:\\foo'), true);
+				assert.strictEqual(pathEquals('C:\\foo\\', 'C:\\foo'), true);
+				assert.strictEqual(pathEquals('C:\\foo', 'C:\\bar'), false);
+			}
+		});
+
+		test('drive root "C:\\" (win32)', function () {
+			if (process.platform === 'win32') {
+				assert.strictEqual(pathEquals('C:\\', 'C:\\'), true);
+				assert.strictEqual(pathEquals('C:\\', 'C:\\foo'), false);
+			}
+		});
+	});
+
+	suite('relativePath', () => {
+		test('root path "/" as base (chroot environments)', function () {
+			if (process.platform !== 'win32') {
+				assert.strictEqual(relativePath('/', '/foo'), 'foo');
+				assert.strictEqual(relativePath('/', '/foo/bar'), 'foo/bar');
+			}
+		});
+
+		test('drive root "C:\\" as base (win32)', function () {
+			if (process.platform === 'win32') {
+				assert.strictEqual(relativePath('C:\\', 'C:\\foo'), 'foo');
+				assert.strictEqual(relativePath('C:\\', 'C:\\foo\\bar'), 'foo\\bar');
+			}
+		});
+	});
+
 	suite('splitInChunks', () => {
 		test('unit tests', function () {
 			assert.deepStrictEqual(
diff --git a/extensions/git/src/util.ts b/extensions/git/src/util.ts
index dfe3c4e07757d..0b8c2eb4d8d77 100644
--- a/extensions/git/src/util.ts
+++ b/extensions/git/src/util.ts
@@ -312,9 +312,9 @@ function normalizePath(path: string): string {
 		path = path.toLowerCase();
 	}
 
-	// Trailing separator
-	if (/[/\\]$/.test(path)) {
-		// Remove trailing separator
+	// Trailing separator — only strip when the path is not
+	// a filesystem root (e.g., "/" on POSIX, "C:\" or UNC roots on Windows).
+	if (/[/\\]$/.test(path) && path !== dirname(path)) {
 		path = path.substring(0, path.length - 1);
 	}