diff --git a/pkg/analysis_server/test/lsp/completion_dart_test.dart b/pkg/analysis_server/test/lsp/completion_dart_test.dart
index 4783dfe93d7f..2474fa8c503e 100644
--- a/pkg/analysis_server/test/lsp/completion_dart_test.dart
+++ b/pkg/analysis_server/test/lsp/completion_dart_test.dart
@@ -3779,11 +3779,6 @@ void f() {
   }
 
   Future<void> test_snippets_testBlock() async {
-    // This test fails when running on macOS using Windows style paths. This
-    // is because DartSnippetProducer.isInTestDirectory compares a path using
-    // the tests PathContext (eg. backslashes when running as Windows-on-macOS)
-    // to `LinterContextImpl.testDirectories` which are always using native
-    // paths.
     mainFilePath = join(projectFolderPath, 'test', 'foo_test.dart');
     mainFileUri = pathContext.toUri(mainFilePath);
     final content = '''
diff --git a/pkg/analysis_server/test/lsp/initialization_test.dart b/pkg/analysis_server/test/lsp/initialization_test.dart
index 1fbba0171356..f703e14c364d 100644
--- a/pkg/analysis_server/test/lsp/initialization_test.dart
+++ b/pkg/analysis_server/test/lsp/initialization_test.dart
@@ -855,6 +855,11 @@ class InitializationTest extends AbstractLspAnalysisServerTest {
     expect(server.contextManager.includedPaths, equals([projectFolderPath]));
   }
 
+  Future<void> test_initialize_rootUri_encodedDriveLetterColon() async {
+    await initialize(rootUri: withEncodedDriveLetterColon(projectFolderUri));
+    expect(server.contextManager.includedPaths, equals([projectFolderPath]));
+  }
+
   Future<void> test_initialize_rootUri_trailingSlash() async {
     await initialize(rootUri: withTrailingSlashUri(projectFolderUri));
     expect(server.contextManager.includedPaths, equals([projectFolderPath]));
@@ -865,6 +870,13 @@ class InitializationTest extends AbstractLspAnalysisServerTest {
     expect(server.contextManager.includedPaths, equals([projectFolderPath]));
   }
 
+  Future<void>
+      test_initialize_workspaceFolders_encodedDriveLetterColon() async {
+    await initialize(
+        workspaceFolders: [withEncodedDriveLetterColon(projectFolderUri)]);
+    expect(server.contextManager.includedPaths, equals([projectFolderPath]));
+  }
+
   Future<void> test_initialize_workspaceFolders_trailingSlash() async {
     await initialize(
         workspaceFolders: [withTrailingSlashUri(projectFolderUri)]);
diff --git a/pkg/analysis_server/test/lsp/server_abstract.dart b/pkg/analysis_server/test/lsp/server_abstract.dart
index d6d43b9cd161..3d208cabe8ad 100644
--- a/pkg/analysis_server/test/lsp/server_abstract.dart
+++ b/pkg/analysis_server/test/lsp/server_abstract.dart
@@ -339,6 +339,13 @@ analyzer:
     return verifier;
   }
 
+  /// Encodes any drive letter colon in the URI.
+  ///
+  /// file:///C:/foo -> file:///C%3A/foo
+  Uri withEncodedDriveLetterColon(Uri uri) {
+    return uri.replace(path: uri.path.replaceAll(':', '%3A'));
+  }
+
   /// Adds a trailing slash (direction based on path context) to [path].
   ///
   /// Throws if the path already has a trailing slash.
diff --git a/pkg/analysis_server/test/lsp/server_test.dart b/pkg/analysis_server/test/lsp/server_test.dart
index 696ef28dab40..4ec18106dd27 100644
--- a/pkg/analysis_server/test/lsp/server_test.dart
+++ b/pkg/analysis_server/test/lsp/server_test.dart
@@ -209,8 +209,6 @@ class ServerTest extends AbstractLspAnalysisServerTest {
     await initialize();
     await expectLater(
       getHover(missingDriveLetterFileUri, startOfDocPos),
-      // The pathContext.toUri() above translates to a non-file:// URI of just
-      // 'a/b.dart' so will get the not-file-scheme error message.
       throwsA(isResponseError(ServerErrorCodes.InvalidFilePath,
           message: 'URI was not an absolute file path (missing drive letter)')),
     );