diff --git a/extensions/markdown-language-features/src/languageFeatures/copyFiles/pasteUrlProvider.ts b/extensions/markdown-language-features/src/languageFeatures/copyFiles/pasteUrlProvider.ts
index 4968f3cb227..a57f0d39005 100644
--- a/extensions/markdown-language-features/src/languageFeatures/copyFiles/pasteUrlProvider.ts
+++ b/extensions/markdown-language-features/src/languageFeatures/copyFiles/pasteUrlProvider.ts
@@ -89,6 +89,7 @@ const smartPasteLineRegexes = [
 	{ regex: /\$\$[\s\S]*?\$\$/gm }, // In a fenced math block
 	{ regex: /`[^`]*`/g }, // In inline code
 	{ regex: /\$[^$]*\$/g }, // In inline math
+	{ regex: /<[^<>\s]*>/g }, // Autolink
 	{ regex: /^[ ]{0,3}\[\w+\]:\s.*$/g, isWholeLine: true }, // Block link definition (needed as tokens are not generated for these)
 ];
 
diff --git a/extensions/markdown-language-features/src/test/pasteUrl.test.ts b/extensions/markdown-language-features/src/test/pasteUrl.test.ts
index 88b996de37d..df863a25652 100644
--- a/extensions/markdown-language-features/src/test/pasteUrl.test.ts
+++ b/extensions/markdown-language-features/src/test/pasteUrl.test.ts
@@ -300,5 +300,11 @@ suite('createEditAddingLinksForUriList', () => {
 				await shouldInsertMarkdownLinkByDefault(createNewMarkdownEngine(), makeTestDoc('   \r\n\r\n'), PasteUrlAsMarkdownLink.SmartWithSelection, [new vscode.Range(0, 0, 0, 7)], noopToken),
 				false);
 		});
+
+		test('Smart should be disabled inside of autolinks', async () => {
+			assert.strictEqual(
+				await shouldInsertMarkdownLinkByDefault(createNewMarkdownEngine(), makeTestDoc('<>'), PasteUrlAsMarkdownLink.Smart, [new vscode.Range(0, 1, 0, 1)], noopToken),
+				false);
+		});
 	});
 });