diff --git a/extensions/markdown-language-features/src/features/smartSelect.ts b/extensions/markdown-language-features/src/features/smartSelect.ts
index 0fca6a5483c..ae6b79faa34 100644
--- a/extensions/markdown-language-features/src/features/smartSelect.ts
+++ b/extensions/markdown-language-features/src/features/smartSelect.ts
@@ -131,9 +131,17 @@ function createInlineRange(document: vscode.TextDocument, cursorPosition: vscode
 	const lineText = document.lineAt(cursorPosition.line).text;
 	const boldSelection = createBoldRange(lineText, cursorPosition.character, cursorPosition.line, parent);
 	const italicSelection = createOtherInlineRange(lineText, cursorPosition.character, cursorPosition.line, true, parent);
-	const linkSelection = createLinkRange(lineText, cursorPosition.character, cursorPosition.line, boldSelection ? boldSelection : italicSelection || parent);
+	let comboSelection: vscode.SelectionRange | undefined;
+	if (boldSelection && italicSelection && !boldSelection.range.isEqual(italicSelection.range)) {
+		if (boldSelection.range.contains(italicSelection.range)) {
+			comboSelection = createOtherInlineRange(lineText, cursorPosition.character, cursorPosition.line, true, boldSelection);
+		} else if (italicSelection.range.contains(boldSelection.range)) {
+			comboSelection = createBoldRange(lineText, cursorPosition.character, cursorPosition.line, italicSelection);
+		}
+	}
+	const linkSelection = createLinkRange(lineText, cursorPosition.character, cursorPosition.line, comboSelection || boldSelection || italicSelection || parent);
 	const inlineCodeBlockSelection = createOtherInlineRange(lineText, cursorPosition.character, cursorPosition.line, false, linkSelection || parent);
-	return inlineCodeBlockSelection || linkSelection || boldSelection || italicSelection;
+	return inlineCodeBlockSelection || linkSelection || comboSelection || boldSelection || italicSelection;
 }
 
 function createFencedRange(token: Token, cursorLine: number, document: vscode.TextDocument, parent?: vscode.SelectionRange): vscode.SelectionRange {
@@ -154,61 +162,31 @@ function createFencedRange(token: Token, cursorLine: number, document: vscode.Te
 }
 
 function createBoldRange(lineText: string, cursorChar: number, cursorLine: number, parent?: vscode.SelectionRange): vscode.SelectionRange | undefined {
-	// find closest ** that occurs before cursor position
-	let startBold = lineText.substring(0, cursorChar).lastIndexOf('**');
-
-	// find closest ** that occurs after the start **
-	const endBoldIndex = lineText.substring(startBold + 2).indexOf('**');
-	let endBold = startBold + 2 + lineText.substring(startBold + 2).indexOf('**');
-
-	if (startBold >= 0 && endBoldIndex >= 0 && startBold + 1 < endBold && startBold <= cursorChar && endBold >= cursorChar) {
-		const range = new vscode.Range(cursorLine, startBold, cursorLine, endBold + 2);
-		// **content cursor content** so select content then ** on both sides
-		const contentRange = new vscode.Range(cursorLine, startBold + 2, cursorLine, endBold);
-		return new vscode.SelectionRange(contentRange, new vscode.SelectionRange(range, parent));
-	} else if (startBold >= 0) {
-		// **content**cursor or **content*cursor*
-		// find end ** from end of start ** to end of line (since the cursor is within the end stars)
-		let adjustedEnd = startBold + 2 + lineText.substring(startBold + 2).indexOf('**');
-		startBold = lineText.substring(0, adjustedEnd - 2).lastIndexOf('**');
-		if (adjustedEnd >= 0 && cursorChar === adjustedEnd || cursorChar === adjustedEnd + 1) {
-			if (lineText.charAt(adjustedEnd + 1) === '*') {
-				// *cursor* so need to extend end to include the second *
-				adjustedEnd += 1;
-			}
-			return new vscode.SelectionRange(new vscode.Range(cursorLine, startBold, cursorLine, adjustedEnd + 1), parent);
-		}
-	} else if (endBold > 0) {
-		// cursor**content** or *cursor*content**
-		// find start ** from start of string to cursor + 2 (since the cursor is within the start stars)
-		const adjustedStart = lineText.substring(0, cursorChar + 2).lastIndexOf('**');
-		endBold = adjustedStart + 2 + lineText.substring(adjustedStart + 2).indexOf('**');
-		if (adjustedStart >= 0 && adjustedStart === cursorChar || adjustedStart === cursorChar - 1) {
-			return new vscode.SelectionRange(new vscode.Range(cursorLine, adjustedStart, cursorLine, endBold + 2), parent);
-		}
+	const regex = /(?:^|(?<=\s))(?:\*\*\s*([^*]+)(?:\*\s*([^*]+)\s*?\*)*([^*]+)\s*?\*\*)/g;
+	const matches = [...lineText.matchAll(regex)].filter(match => lineText.indexOf(match[0]) <= cursorChar && lineText.indexOf(match[0]) + match[0].length >= cursorChar);
+	if (matches.length > 0) {
+		// should only be one match, so select first and index 0 contains the entire match
+		const bold = matches[0][0];
+		const startIndex = lineText.indexOf(bold);
+		const cursorOnStars = cursorChar === startIndex || cursorChar === startIndex + 1 || cursorChar === startIndex + bold.length || cursorChar === startIndex + bold.length - 1;
+		const contentAndStars = new vscode.SelectionRange(new vscode.Range(cursorLine, startIndex, cursorLine, startIndex + bold.length), parent);
+		const content = new vscode.SelectionRange(new vscode.Range(cursorLine, startIndex + 2, cursorLine, startIndex + bold.length - 2), contentAndStars);
+		return cursorOnStars ? contentAndStars : content;
 	}
 	return undefined;
 }
 
 function createOtherInlineRange(lineText: string, cursorChar: number, cursorLine: number, isItalic: boolean, parent?: vscode.SelectionRange): vscode.SelectionRange | undefined {
-	const type = isItalic ? '*' : '`';
-	const start = lineText.substring(0, cursorChar + 1).lastIndexOf(type);
-	let end = lineText.substring(cursorChar).indexOf(type);
-
-	if (start >= 0 && end >= 0) {
-		end += cursorChar;
-		// ensure there's no * or ` before end
-		const intermediate = lineText.substring(start + 1, end - 1).indexOf(type);
-		if (intermediate < 0) {
-			const range = new vscode.Range(cursorLine, start, cursorLine, end + 1);
-			if (cursorChar > start && cursorChar <= end) {
-				// within the content so select content then include the stars or backticks
-				const contentRange = new vscode.Range(cursorLine, start + 1, cursorLine, end);
-				return new vscode.SelectionRange(contentRange, new vscode.SelectionRange(range, parent));
-			} else if (cursorChar === start) {
-				return new vscode.SelectionRange(range, parent);
-			}
-		}
+	const regex = isItalic ? /(?:^|(?<=\s))(?:\*\s*([^*]+)(?:\*\*\s*([^*]+)\s*?\*\*)*([^*]+)\s*?\*)/g : /\`[^\`]*\`/g;
+	const matches = [...lineText.matchAll(regex)].filter(match => lineText.indexOf(match[0]) <= cursorChar && lineText.indexOf(match[0]) + match[0].length >= cursorChar);
+	if (matches.length > 0) {
+		// should only be one match, so select first and index 0 contains the entire match
+		const match = matches[0][0];
+		const startIndex = lineText.indexOf(match);
+		const cursorOnType = cursorChar === startIndex || cursorChar === startIndex + match.length;
+		const contentAndType = new vscode.SelectionRange(new vscode.Range(cursorLine, startIndex, cursorLine, startIndex + match.length), parent);
+		const content = new vscode.SelectionRange(new vscode.Range(cursorLine, startIndex + 1, cursorLine, startIndex + match.length - 1), contentAndType);
+		return cursorOnType ? contentAndType : content;
 	}
 	return undefined;
 }
@@ -228,11 +206,12 @@ function createLinkRange(lineText: string, cursorChar: number, cursorLine: numbe
 		// determine if cursor is within [text] or (url) in order to know which should be selected
 		const nearestType = cursorChar >= lineText.indexOf(linkText) && cursorChar < lineText.indexOf(linkText) + linkText.length ? linkText : url;
 
+		const indexOfType = lineText.indexOf(nearestType);
 		// determine if cursor is on a bracket or paren and if so, return the [content] or (content), skipping over the content range
-		const cursorOnType = cursorChar === lineText.indexOf(nearestType) || cursorChar === lineText.indexOf(nearestType) + nearestType.length;
+		const cursorOnType = cursorChar === indexOfType || cursorChar === indexOfType + nearestType.length;
 
-		const contentAndNearestType = new vscode.SelectionRange(new vscode.Range(cursorLine, lineText.indexOf(nearestType), cursorLine, lineText.indexOf(nearestType) + nearestType.length), linkRange);
-		const content = new vscode.SelectionRange(new vscode.Range(cursorLine, lineText.indexOf(nearestType) + 1, cursorLine, lineText.indexOf(nearestType) + nearestType.length - 1), contentAndNearestType);
+		const contentAndNearestType = new vscode.SelectionRange(new vscode.Range(cursorLine, indexOfType, cursorLine, indexOfType + nearestType.length), linkRange);
+		const content = new vscode.SelectionRange(new vscode.Range(cursorLine, indexOfType + 1, cursorLine, indexOfType + nearestType.length - 1), contentAndNearestType);
 		return cursorOnType ? contentAndNearestType : content;
 	}
 	return undefined;
diff --git a/extensions/markdown-language-features/src/test/smartSelect.test.ts b/extensions/markdown-language-features/src/test/smartSelect.test.ts
index 98f2a5de607..15fb24e32ff 100644
--- a/extensions/markdown-language-features/src/test/smartSelect.test.ts
+++ b/extensions/markdown-language-features/src/test/smartSelect.test.ts
@@ -520,10 +520,10 @@ suite('markdown.SmartSelect', () => {
 				`paragraph`,
 				`## sub header`,
 				`- list`,
-				`- stuff here [text]**${CURSOR}items in here** and **here**`,
+				`- stuff here [text] **${CURSOR}items in here** and **here**`,
 				`- list`
 			));
-		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]);
+		assertNestedRangesEqual(ranges![0], [6, 22, 6, 45], [6, 20, 6, 47], [6, 0, 6, 60], [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(
@@ -567,6 +567,27 @@ suite('markdown.SmartSelect', () => {
 			));
 		assertNestedRangesEqual(ranges![0], [0, 2, 0, 21], [0, 1, 0, 22], [0, 1, 0, 42], [0, 1, 0, 42], [0, 0, 0, 43], [0, 0, 0, 43]);
 	});
+	test('Smart select italic on end', async () => {
+		const ranges = await getSelectionRangesForDocument(
+			joinLines(
+				`*word1 word2 word3${CURSOR}*`
+			));
+		assertNestedRangesEqual(ranges![0], [0, 1, 0, 28], [0, 0, 0, 29], [0, 0, 0, 29]);
+	});
+	test('Smart select italic then bold', async () => {
+		const ranges = await getSelectionRangesForDocument(
+			joinLines(
+				`outer text **bold words *italic ${CURSOR} words* bold words** outer text`
+			));
+		assertNestedRangesEqual(ranges![0], [0, 25, 0, 48], [0, 24, 0, 49], [0, 13, 0, 60], [0, 11, 0, 62], [0, 0, 0, 73]);
+	});
+	test('Smart select bold then italic', async () => {
+		const ranges = await getSelectionRangesForDocument(
+			joinLines(
+				`outer text *italic words **bold ${CURSOR} words** italic words* outer text`
+			));
+		assertNestedRangesEqual(ranges![0], [0, 27, 0, 48], [0, 25, 0, 50], [0, 12, 0, 63], [0, 11, 0, 64], [0, 0, 0, 75]);
+	});
 });
 
 function assertNestedLineNumbersEqual(range: vscode.SelectionRange, ...expectedRanges: [number, number][]) {