diff --git a/extensions/typescript-language-features/package.json b/extensions/typescript-language-features/package.json
index 7392a267a56..b3f12439bc8 100644
--- a/extensions/typescript-language-features/package.json
+++ b/extensions/typescript-language-features/package.json
@@ -638,6 +638,42 @@
           "description": "%typescript.preferences.importModuleSpecifier%",
           "scope": "resource"
         },
+        "javascript.preferences.importModuleSpecifierEnding": {
+          "type": "string",
+          "enum": [
+            "auto",
+            "minimal",
+            "index",
+            "js"
+          ],
+          "markdownEnumDescriptions": [
+            "%typescript.preferences.importModuleSpecifierEnding.auto%",
+            "%typescript.preferences.importModuleSpecifierEnding.minimal%",
+            "%typescript.preferences.importModuleSpecifierEnding.index%",
+            "%typescript.preferences.importModuleSpecifierEnding.js%"
+          ],
+          "default": "auto",
+          "description": "%typescript.preferences.importModuleSpecifierEnding%",
+          "scope": "resource"
+        },
+        "typescript.preferences.importModuleSpecifierEnding": {
+          "type": "string",
+          "enum": [
+            "auto",
+            "minimal",
+            "index",
+            "js"
+          ],
+          "markdownEnumDescriptions": [
+            "%typescript.preferences.importModuleSpecifierEnding.auto%",
+            "%typescript.preferences.importModuleSpecifierEnding.minimal%",
+            "%typescript.preferences.importModuleSpecifierEnding.index%",
+            "%typescript.preferences.importModuleSpecifierEnding.js%"
+          ],
+          "default": "auto",
+          "description": "%typescript.preferences.importModuleSpecifierEnding%",
+          "scope": "resource"
+        },
         "javascript.preferences.renameShorthandProperties": {
           "type": "boolean",
           "default": true,
diff --git a/extensions/typescript-language-features/package.nls.json b/extensions/typescript-language-features/package.nls.json
index a421936acb9..a2bf1f3eeed 100644
--- a/extensions/typescript-language-features/package.nls.json
+++ b/extensions/typescript-language-features/package.nls.json
@@ -70,6 +70,11 @@
 	"typescript.preferences.importModuleSpecifier.auto": "Automatically select import path style. Prefers using a relative import if `baseUrl` is configured and the relative path has fewer segments than the non-relative import.",
 	"typescript.preferences.importModuleSpecifier.relative": "Relative to the file location.",
 	"typescript.preferences.importModuleSpecifier.nonRelative": "Based on the `baseUrl` configured in your `jsconfig.json` / `tsconfig.json`.",
+	"typescript.preferences.importModuleSpecifierEnding": "Preferred path ending for auto imports.",
+	"typescript.preferences.importModuleSpecifierEnding.auto": "Use project settings to select a default.",
+	"typescript.preferences.importModuleSpecifierEnding.minimal": "Shorten `./component/index.js` to `./component`.",
+	"typescript.preferences.importModuleSpecifierEnding.index": "Shorten `./component/index.js` to `./component/index`",
+	"typescript.preferences.importModuleSpecifierEnding.js": "Do not shorten path endings; include the `.js` extension.",
 	"typescript.updateImportsOnFileMove.enabled": "Enable/disable automatic updating of import paths when you rename or move a file in VS Code. Requires using TypeScript 2.9 or newer in the workspace.",
 	"typescript.updateImportsOnFileMove.enabled.prompt": "Prompt on each rename.",
 	"typescript.updateImportsOnFileMove.enabled.always": "Always update paths automatically.",
diff --git a/extensions/typescript-language-features/src/features/fileConfigurationManager.ts b/extensions/typescript-language-features/src/features/fileConfigurationManager.ts
index 4a625231458..be7431eac9f 100644
--- a/extensions/typescript-language-features/src/features/fileConfigurationManager.ts
+++ b/extensions/typescript-language-features/src/features/fileConfigurationManager.ts
@@ -179,13 +179,18 @@ export default class FileConfigurationManager extends Disposable {
 			isTypeScriptDocument(document) ? 'typescript.preferences' : 'javascript.preferences',
 			document.uri);
 
-		return {
+		// `importModuleSpecifierEnding` added to `Proto.UserPreferences` in TypeScript 3.9:
+		// remove intersection type after upgrading TypeScript.
+		const preferences: Proto.UserPreferences & { importModuleSpecifierEnding?: string } = {
 			quotePreference: this.getQuoteStylePreference(config),
 			importModuleSpecifierPreference: getImportModuleSpecifierPreference(config),
+			importModuleSpecifierEnding: getImportModuleSpecifierEndingPreference(config),
 			allowTextChangesInNewFiles: document.uri.scheme === fileSchemes.file,
 			providePrefixAndSuffixTextForRename: config.get<boolean>('renameShorthandProperties', true),
 			allowRenameOfImportPath: true,
 		};
+
+		return preferences;
 	}
 
 	private getQuoteStylePreference(config: vscode.WorkspaceConfiguration) {
@@ -204,3 +209,12 @@ function getImportModuleSpecifierPreference(config: vscode.WorkspaceConfiguratio
 		default: return undefined;
 	}
 }
+
+function getImportModuleSpecifierEndingPreference(config: vscode.WorkspaceConfiguration) {
+	switch (config.get<string>('importModuleSpecifierEnding')) {
+		case 'minimal': return 'minimal';
+		case 'index': return 'index';
+		case 'js': return 'js';
+		default: return 'auto';
+	}
+}