try this

Author: Ocean-OS

packages/site-kit/src/lib/markdown/utils.ts

@@ -70,7 +70,7 @@ export function smart_quotes(
 		if (html && char === '&') {
 			if (str.slice(index, index + 5) === ''') {
 				const left: boolean =
-					((first && stack.at(-1) !== "'") || (index > 1 && before === '=')) &&
+					((first && before === '') || stack.at(-1) !== "'" || (index > 1 && before === '=')) &&
 					!opening_squo_chars.test(before);
 				res += `&${left ? 'l' : 'r'}squo;`;
 				index += 4;
@@ -81,7 +81,9 @@ export function smart_quotes(
 				}
 			} else if (str.slice(index, index + 6) === '"') {
 				const left: boolean =
-					(first && stack.at(-1) !== '"') || (index > 1 && str.charAt(index - 1) === '=');
+					(first && before === '') ||
+					stack.at(-1) !== '"' ||
+					(index > 1 && str.charAt(index - 1) === '=');
 				res += `&${left ? 'l' : 'r'}dquo`;
 				index += 5;
 				if (!left) {
@@ -94,7 +96,7 @@ export function smart_quotes(
 			}
 		} else if (!html && (char === '"' || char === "'")) {
 			let left: boolean =
-				((first && stack.at(-1) !== char) || (index > 1 && before === '=')) &&
+				((first && before === '') || stack.at(-1) !== char || (index > 1 && before === '=')) &&
 				!(char === "'" && !opening_squo_chars.test(before));
 			let double = char === '"';
 			res += double ? (left ? '“' : '”') : left ? '‘' : '’';