diff --git a/packages/cli-utils/src/commands/doctor/helpers/vscode.ts b/packages/cli-utils/src/commands/doctor/helpers/vscode.ts
index 24cdcaa6..8fb63646 100644
--- a/packages/cli-utils/src/commands/doctor/helpers/vscode.ts
+++ b/packages/cli-utils/src/commands/doctor/helpers/vscode.ts
@@ -50,8 +50,7 @@ export const loadSuggestedExtensionsList = async (
 
 /** Loads list of installed VSCode extensions */
 export const loadExtensionsList = async (): Promise<readonly string[]> => {
-  if (!process.env.HOME) return [];
-  const vscodeFolder = path.resolve(process.env.HOME, '.vscode');
+  const vscodeFolder = path.resolve(process.env.HOME!, '.vscode');
   const configFile = path.resolve(vscodeFolder, 'extensions', 'extensions.json');
   if (!(await stat(configFile))) return [];
   let json: unknown;
@@ -71,3 +70,55 @@ export const loadExtensionsList = async (): Promise<readonly string[]> => {
     })
     .filter((x): x is string => !!x);
 };
+
+/** Load the global VSCode settings */
+export const loadGlobalSettings = async (): Promise<{ path: string; json: object } | undefined> => {
+  const globalPath =
+    process.platform === 'darwin'
+      ? path.join(
+          process.env.HOME!,
+          'Library',
+          'Application Support',
+          'Code',
+          'User',
+          'settings.json'
+        )
+      : path.join(process.env.HOME!, '.config', 'Code', 'User', 'settings.json');
+
+  try {
+    const globalJson = await jsonParse(globalPath);
+    if (globalJson && typeof globalJson === 'object') {
+      return { path: globalPath, json: globalJson };
+    }
+  } catch {}
+  return undefined;
+};
+
+/** Load the workspace VSCode settings */
+export const loadWorkspaceSettings = async (): Promise<
+  { path: string; json: object } | undefined
+> => {
+  const settingsPath = path.resolve(process.cwd(), '.vscode', 'settings.json');
+  if (await stat(settingsPath, FileType.File)) {
+    try {
+      const workspaceJson = await jsonParse(settingsPath);
+      if (workspaceJson && typeof workspaceJson === 'object') {
+        return { path: settingsPath, json: workspaceJson };
+      }
+    } catch {}
+  }
+  return undefined;
+};
+
+/** Load all VSCode settings */
+export const loadSettings = async (): Promise<{
+  workspace?: { path: string; json: object };
+  global?: { path: string; json: object };
+}> => {
+  const [workspace, global] = await Promise.all([loadWorkspaceSettings(), loadGlobalSettings()]);
+
+  return {
+    workspace,
+    global,
+  };
+};
diff --git a/packages/cli-utils/src/commands/doctor/runner.ts b/packages/cli-utils/src/commands/doctor/runner.ts
index 60663cf1..487bf1c3 100644
--- a/packages/cli-utils/src/commands/doctor/runner.ts
+++ b/packages/cli-utils/src/commands/doctor/runner.ts
@@ -191,6 +191,49 @@ async function* runVSCodeChecks(): AsyncIterable<ComposeInput> {
             'See: https://marketplace.visualstudio.com/items?itemName=GraphQL.vscode-graphql-syntax\n'
         );
       }
+
+      // Check VSCode settings
+      const locations = await vscode.loadSettings();
+
+      // 1. Check for presence of incompatible settings
+      for (const location of Object.values(locations)) {
+        if (location.json['editor.experimental.preferTreeSitter.typescript']) {
+          if (!hasEndedTask) {
+            hasEndedTask = true;
+            yield logger.warningTask(Messages.CHECK_VSCODE);
+          }
+          yield logger.hintMessage(
+            `The ${logger.code(
+              '"editor.experimental.preferTreeSitter.typescript"'
+            )} VSCode setting can cause problems!\n` +
+              `When enabled it may interfere with extension functionality.\n` +
+              `You may disable the setting here: ${logger.code(location.path)}\n`
+          );
+        }
+      }
+
+      // 2. Check for missing recommended settings
+      const workspaceSettings = locations.workspace;
+      if (
+        !workspaceSettings ||
+        workspaceSettings.json['typescript.tsdk'] !== 'node_modules/typescript/lib' ||
+        !workspaceSettings.json['typescript.enablePromptUseWorkspaceTsdk']
+      ) {
+        if (!hasEndedTask) {
+          hasEndedTask = true;
+          yield logger.warningTask(Messages.CHECK_VSCODE);
+        }
+        yield logger.hintMessage(
+          `A recommended VSCode workspace setting is missing!\n` +
+            `The following are recommended:\n` +
+            `${logger.code(
+              '{\n' +
+                '"typescript.tsdk": "node_modules/typescript/lib",\n' +
+                '"typescript.enablePromptUseWorkspaceTsdk": true\n' +
+                '}\n'
+            )}\n`
+        );
+      }
     }
 
     const hasProblemExtension =