diff --git a/extensions/markdown-language-features/package.json b/extensions/markdown-language-features/package.json
index ddfdaebda7b..c9e2e23d4e8 100644
--- a/extensions/markdown-language-features/package.json
+++ b/extensions/markdown-language-features/package.json
@@ -771,7 +771,7 @@
     "dompurify": "^3.0.5",
     "highlight.js": "^11.8.0",
     "markdown-it": "^12.3.2",
-    "markdown-it-front-matter": "^0.2.1",
+    "markdown-it-front-matter": "^0.2.4",
     "morphdom": "^2.6.1",
     "picomatch": "^2.3.1",
     "vscode-languageclient": "^8.0.2",
diff --git a/extensions/markdown-language-features/src/test/pasteUrl.test.ts b/extensions/markdown-language-features/src/test/pasteUrl.test.ts
index 2afa4465f76..ea4a3f868af 100644
--- a/extensions/markdown-language-features/src/test/pasteUrl.test.ts
+++ b/extensions/markdown-language-features/src/test/pasteUrl.test.ts
@@ -11,6 +11,7 @@ import { InsertMarkdownLink, findValidUriInText, shouldInsertMarkdownLinkByDefau
 import { noopToken } from '../util/cancellation';
 import { UriList } from '../util/uriList';
 import { createNewMarkdownEngine } from './engine';
+import { joinLines } from './util';
 
 function makeTestDoc(contents: string) {
 	return new InMemoryDocument(vscode.Uri.file('test.md'), contents);
@@ -307,5 +308,36 @@ suite('createEditAddingLinksForUriList', () => {
 				await shouldInsertMarkdownLinkByDefault(createNewMarkdownEngine(), makeTestDoc('<>'), InsertMarkdownLink.Smart, [new vscode.Range(0, 1, 0, 1)], noopToken),
 				false);
 		});
+
+		test('Smart should be disabled in frontmatter', async () => {
+			const textDoc = makeTestDoc(joinLines(
+				`---`,
+				`layout: post`,
+				`title: Blogging Like a Hacker`,
+				`---`,
+				``,
+				`Link Text`
+			));
+			assert.strictEqual(
+				await shouldInsertMarkdownLinkByDefault(createNewMarkdownEngine(), textDoc, InsertMarkdownLink.Smart, [new vscode.Range(0, 0, 0, 0)], noopToken),
+				false);
+
+			assert.strictEqual(
+				await shouldInsertMarkdownLinkByDefault(createNewMarkdownEngine(), textDoc, InsertMarkdownLink.Smart, [new vscode.Range(1, 0, 1, 0)], noopToken),
+				false);
+		});
+
+		test('Smart should enabled after frontmatter', async () => {
+			assert.strictEqual(
+				await shouldInsertMarkdownLinkByDefault(createNewMarkdownEngine(), makeTestDoc(joinLines(
+					`---`,
+					`layout: post`,
+					`title: Blogging Like a Hacker`,
+					`---`,
+					``,
+					`Link Text`
+				)), InsertMarkdownLink.Smart, [new vscode.Range(5, 0, 5, 0)], noopToken),
+				true);
+		});
 	});
 });
diff --git a/extensions/markdown-language-features/yarn.lock b/extensions/markdown-language-features/yarn.lock
index 25e16c5379a..2b688e40592 100644
--- a/extensions/markdown-language-features/yarn.lock
+++ b/extensions/markdown-language-features/yarn.lock
@@ -242,10 +242,10 @@ lru-cache@^6.0.0:
   dependencies:
     yallist "^4.0.0"
 
-markdown-it-front-matter@^0.2.1:
-  version "0.2.1"
-  resolved "https://registry.yarnpkg.com/markdown-it-front-matter/-/markdown-it-front-matter-0.2.1.tgz#dca49a827bb3cebb0528452c1d87dff276eb28dc"
-  integrity sha512-ydUIqlKfDscRpRUTRcA3maeeUKn3Cl5EaKZSA+I/f0KOGCBurW7e+bbz59sxqkC3FA9Q2S2+t4mpkH9T0BCM6A==
+markdown-it-front-matter@^0.2.4:
+  version "0.2.4"
+  resolved "https://registry.yarnpkg.com/markdown-it-front-matter/-/markdown-it-front-matter-0.2.4.tgz#cf29bc8222149b53575699357b1ece697bf39507"
+  integrity sha512-25GUs0yjS2hLl8zAemVndeEzThB1p42yxuDEKbd4JlL3jiz+jsm6e56Ya8B0VREOkNxLYB4TTwaoPJ3ElMmW+w==
 
 markdown-it@^12.3.2:
   version "12.3.2"