diff --git a/extensions/markdown-language-features/src/test/inMemoryDocument.ts b/extensions/markdown-language-features/src/test/inMemoryDocument.ts
index 052216f90f5..8f5f6fe78ab 100644
--- a/extensions/markdown-language-features/src/test/inMemoryDocument.ts
+++ b/extensions/markdown-language-features/src/test/inMemoryDocument.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import * as vscode from 'vscode';
-
+import * as os from 'os';
 export class InMemoryDocument implements vscode.TextDocument {
 	private readonly _lines: string[];
 
@@ -13,7 +13,7 @@ export class InMemoryDocument implements vscode.TextDocument {
 		private readonly _contents: string,
 		public readonly version = 1,
 	) {
-		this._lines = this._contents.split(/\n/g);
+		this._lines = this._contents.split(/\r\n|\n/g);
 	}
 
 
@@ -21,7 +21,7 @@ export class InMemoryDocument implements vscode.TextDocument {
 	languageId: string = '';
 	isDirty: boolean = false;
 	isClosed: boolean = false;
-	eol: vscode.EndOfLine = vscode.EndOfLine.LF;
+	eol: vscode.EndOfLine = os.platform() === 'win32' ? vscode.EndOfLine.CRLF : vscode.EndOfLine.LF;
 	notebook: undefined;
 
 	get fileName(): string {
@@ -47,9 +47,9 @@ export class InMemoryDocument implements vscode.TextDocument {
 	}
 	positionAt(offset: number): vscode.Position {
 		const before = this._contents.slice(0, offset);
-		const newLines = before.match(/\n/g);
+		const newLines = before.match(/\r\n|\n/g);
 		const line = newLines ? newLines.length : 0;
-		const preCharacters = before.match(/(\n|^).*$/g);
+		const preCharacters = before.match(/(\r\n|\n|^).*$/g);
 		return new vscode.Position(line, preCharacters ? preCharacters[0].length : 0);
 	}
 	getText(_range?: vscode.Range | undefined): string {
diff --git a/extensions/markdown-language-features/src/test/smartSelect.test.ts b/extensions/markdown-language-features/src/test/smartSelect.test.ts
index 11ed99230c2..98f2a5de607 100644
--- a/extensions/markdown-language-features/src/test/smartSelect.test.ts
+++ b/extensions/markdown-language-features/src/test/smartSelect.test.ts
@@ -483,7 +483,7 @@ suite('markdown.SmartSelect', () => {
 			));
 		assertNestedRangesEqual(ranges![0], [0, 12, 0, 26], [0, 11, 0, 27], [0, 11, 0, 47], [0, 0, 0, 56]);
 	});
-	test.skip('Smart select brackets under header in list', async () => {
+	test('Smart select brackets under header in list', async () => {
 		const ranges = await getSelectionRangesForDocument(
 			joinLines(
 				`# main header 1`,
@@ -495,9 +495,9 @@ suite('markdown.SmartSelect', () => {
 				`- stuff here [te${CURSOR}xt](https://google.com) and here`,
 				`- list`
 			));
-		assertNestedRangesEqual(ranges![0], [6, 14, 6, 28], [6, 13, 6, 29], [6, 13, 6, 49], [6, 0, 6, 59], [5, 0, 7, 6], [4, 0, 7, 6], [1, 0, 7, 6], [0, 0, 7, 6]);
+		assertNestedRangesEqual(ranges![0], [6, 14, 6, 28], [6, 13, 6, 29], [6, 13, 6, 49], [6, 0, 6, 58], [5, 0, 7, 6], [4, 0, 7, 6], [1, 0, 7, 6], [0, 0, 7, 6]);
 	});
-	test.skip('Smart select link under header in list', async () => {
+	test('Smart select link under header in list', async () => {
 		const ranges = await getSelectionRangesForDocument(
 			joinLines(
 				`# main header 1`,
@@ -509,9 +509,9 @@ suite('markdown.SmartSelect', () => {
 				`- stuff here [text](${CURSOR}https://google.com) and here`,
 				`- list`
 			));
-		assertNestedRangesEqual(ranges![0], [6, 20, 6, 48], [6, 19, 6, 49], [6, 13, 6, 49], [6, 0, 6, 59], [5, 0, 7, 6], [4, 0, 7, 6], [1, 0, 7, 6], [0, 0, 7, 6]);
+		assertNestedRangesEqual(ranges![0], [6, 20, 6, 48], [6, 19, 6, 49], [6, 13, 6, 49], [6, 0, 6, 58], [5, 0, 7, 6], [4, 0, 7, 6], [1, 0, 7, 6], [0, 0, 7, 6]);
 	});
-	test.skip('Smart select bold within list where multiple bold elements exists', async () => {
+	test('Smart select bold within list where multiple bold elements exists', async () => {
 		const ranges = await getSelectionRangesForDocument(
 			joinLines(
 				`# main header 1`,
@@ -523,7 +523,7 @@ suite('markdown.SmartSelect', () => {
 				`- stuff here [text]**${CURSOR}items in here** and **here**`,
 				`- list`
 			));
-		assertNestedRangesEqual(ranges![0], [6, 21, 6, 44], [6, 19, 6, 46], [6, 0, 6, 60], [5, 0, 7, 6], [4, 0, 7, 6], [1, 0, 7, 6], [0, 0, 7, 6]);
+		assertNestedRangesEqual(ranges![0], [6, 21, 6, 44], [6, 19, 6, 46], [6, 0, 6, 59], [5, 0, 7, 6], [4, 0, 7, 6], [1, 0, 7, 6], [0, 0, 7, 6]);
 	});
 	test('Smart select link in paragraph with multiple links', async () => {
 		const ranges = await getSelectionRangesForDocument(