diff --git a/extensions/markdown-language-features/src/languageFeatures/copyFiles/shared.ts b/extensions/markdown-language-features/src/languageFeatures/copyFiles/shared.ts
index 768fafded3d33..082f569b0b102 100644
--- a/extensions/markdown-language-features/src/languageFeatures/copyFiles/shared.ts
+++ b/extensions/markdown-language-features/src/languageFeatures/copyFiles/shared.ts
@@ -151,6 +151,9 @@ export async function createEditAddingLinksForUriList(
 
 export function checkSmartPaste(document: SkinnyTextDocument, selectedRange: vscode.Range): SmartPaste {
 	const SmartPaste: SmartPaste = { pasteAsMarkdownLink: true, updateTitle: false };
+	if (selectedRange.isEmpty || /^[\s\n]*$/.test(document.getText(selectedRange))) {
+		return { pasteAsMarkdownLink: false, updateTitle: false };
+	}
 	for (const regex of smartPasteRegexes) {
 		const matches = [...document.getText().matchAll(regex.regex)];
 		for (const match of matches) {
diff --git a/extensions/markdown-language-features/src/test/markdownLink.test.ts b/extensions/markdown-language-features/src/test/markdownLink.test.ts
index bf7e82b439c97..05a08b1046340 100644
--- a/extensions/markdown-language-features/src/test/markdownLink.test.ts
+++ b/extensions/markdown-language-features/src/test/markdownLink.test.ts
@@ -148,11 +148,24 @@ suite('createEditAddingLinksForUriList', () => {
 		};
 
 		test('Should evaluate pasteAsMarkdownLink as true for selected plain text', () => {
-			const range = new vscode.Range(0, 5, 0, 5);
+			const range = new vscode.Range(0, 0, 0, 12);
 			const smartPaste = checkSmartPaste(skinnyDocument, range);
 			assert.strictEqual(smartPaste.pasteAsMarkdownLink, true);
 		});
 
+		test('Should evaluate pasteAsMarkdownLink as false for no selection', () => {
+			const range = new vscode.Range(0, 0, 0, 0);
+			const smartPaste = checkSmartPaste(skinnyDocument, range);
+			assert.strictEqual(smartPaste.pasteAsMarkdownLink, false);
+		});
+
+		test('Should evaluate pasteAsMarkdownLink as false for selected whitespace and new lines', () => {
+			skinnyDocument.getText = function () { return '   \r\n\r\n'; };
+			const range = new vscode.Range(0, 0, 0, 7);
+			const smartPaste = checkSmartPaste(skinnyDocument, range);
+			assert.strictEqual(smartPaste.pasteAsMarkdownLink, false);
+		});
+
 		test('Should evaluate pasteAsMarkdownLink as false for pasting within a backtick code block', () => {
 			skinnyDocument.getText = function () { return '```\r\n\r\n```'; };
 			const range = new vscode.Range(0, 5, 0, 5);