diff --git a/pkg/analysis_server/lib/src/services/correction/organize_imports.dart b/pkg/analysis_server/lib/src/services/correction/organize_imports.dart
index a735f2cf723a..c89559fd2664 100644
--- a/pkg/analysis_server/lib/src/services/correction/organize_imports.dart
+++ b/pkg/analysis_server/lib/src/services/correction/organize_imports.dart
@@ -371,7 +371,9 @@ class _DirectiveInfo implements Comparable<_DirectiveInfo> {
   /// Consider finding a way to share this code!
   static int _compareUri(String a, String b) {
     if (!a.startsWith('package:') || !b.startsWith('package:')) {
-      return a.compareTo(b);
+      if (!a.startsWith('/') && !b.startsWith('/')) {
+        return a.compareTo(b);
+      }
     }
     var indexA = a.indexOf('/');
     var indexB = b.indexOf('/');
diff --git a/pkg/linter/lib/src/rules/directives_ordering.dart b/pkg/linter/lib/src/rules/directives_ordering.dart
index 0208dd6ce3d5..7ed9cbfc52f1 100644
--- a/pkg/linter/lib/src/rules/directives_ordering.dart
+++ b/pkg/linter/lib/src/rules/directives_ordering.dart
@@ -117,7 +117,9 @@ const _importKeyword = 'import';
 /// Package is everything until the first `/`.
 int compareDirectives(String a, String b) {
   if (!a.startsWith('package:') || !b.startsWith('package:')) {
-    return a.compareTo(b);
+    if (!a.startsWith('/') && !b.startsWith('/')) {
+      return a.compareTo(b);
+    }
   }
   var indexA = a.indexOf('/');
   var indexB = b.indexOf('/');
diff --git a/pkg/linter/test/directives_ordering_test.dart b/pkg/linter/test/directives_ordering_test.dart
new file mode 100644
index 000000000000..22ffa28809ff
--- /dev/null
+++ b/pkg/linter/test/directives_ordering_test.dart
@@ -0,0 +1,56 @@
+// Copyright (c) 2024, the Dart project authors. Please see the AUTHORS file
+// for details. All rights reserved. Use of this source code is governed by a
+// BSD-style license that can be found in the LICENSE file.
+
+import 'package:linter/src/rules/directives_ordering.dart';
+import 'package:test/test.dart';
+
+void main() {
+  group(compareDirectives, () {
+    void checkImportGroup(List<String> correctlyOrderedImports) {
+      for (int i = 0; i < correctlyOrderedImports.length; i++) {
+        var a = correctlyOrderedImports[i];
+        expect(compareDirectives(a, a), 0,
+            reason: '"$a" sorts the same as itself');
+
+        for (int j = i + 1; j < correctlyOrderedImports.length; j++) {
+          var b = correctlyOrderedImports[j];
+          expect(compareDirectives(a, b), lessThan(0),
+              reason: '"$a" sorts before "$b"');
+          expect(compareDirectives(b, a), greaterThan(0),
+              reason: '"$b" sorts after "$a"');
+        }
+      }
+    }
+
+    test('dart: imports', () {
+      checkImportGroup(const [
+        'dart:aaa',
+        'dart:bbb',
+      ]);
+    });
+
+    test('package: imports', () {
+      checkImportGroup(const [
+        'package:aa/bb.dart',
+        'package:aaa/aaa.dart',
+        'package:aaa/ccc.dart',
+        'package:bbb/bbb.dart',
+      ]);
+    });
+
+    test('relative imports', () {
+      checkImportGroup(const [
+        '/foo5.dart',
+        '../../foo4.dart',
+        '../foo2/a.dart',
+        '../foo3.dart',
+        './foo2.dart',
+        'a.dart',
+        'aaa/aaa.dart',
+        'bbb/bbb.dart',
+        'foo1.dart',
+      ]);
+    });
+  });
+}
diff --git a/pkg/linter/test/rules/directives_ordering_test.dart b/pkg/linter/test/rules/directives_ordering_test.dart
index 0c4871571f28..1c6dae70237b 100644
--- a/pkg/linter/test/rules/directives_ordering_test.dart
+++ b/pkg/linter/test/rules/directives_ordering_test.dart
@@ -213,6 +213,7 @@ import 'foo4.dart';
 
   test_sortDirectiveSectionsAlphabetically_dotInRelativePath_import_ok() async {
     await assertNoDiagnostics(r'''
+import '/foo5.dart';
 import '../../foo4.dart';
 import '../foo3.dart';
 import './foo2.dart';