diff --git a/telethon/extensions/html.py b/telethon/extensions/html.py
index 564dcf13..201312ac 100644
--- a/telethon/extensions/html.py
+++ b/telethon/extensions/html.py
@@ -167,21 +167,21 @@ def unparse(text: str, entities: Iterable[TypeMessageEntity]) -> str:
 
     text = add_surrogate(text)
     insert_at = []
-    for entity in entities:
+    for i, entity in enumerate(entities):
         s = entity.offset
         e = entity.offset + entity.length
         delimiter = ENTITY_TO_FORMATTER.get(type(entity), None)
         if delimiter:
             if callable(delimiter):
                 delimiter = delimiter(entity, text[s:e])
-            insert_at.append((s, delimiter[0]))
-            insert_at.append((e, delimiter[1]))
+            insert_at.append((s, i, delimiter[0]))
+            insert_at.append((e, len(entities) - i, delimiter[1]))
 
-    insert_at.sort(key=lambda t: t[0])
+    insert_at.sort(key=lambda t: (t[0], t[1]))
     next_escape_bound = len(text)
     while insert_at:
         # Same logic as markdown.py
-        at, what = insert_at.pop()
+        at, _, what = insert_at.pop()
         while within_surrogate(text, at):
             at += 1
 
diff --git a/telethon/extensions/markdown.py b/telethon/extensions/markdown.py
index d52fc347..78f28385 100644
--- a/telethon/extensions/markdown.py
+++ b/telethon/extensions/markdown.py
@@ -164,13 +164,13 @@ def unparse(text, entities, delimiters=None, url_fmt=None):
     text = add_surrogate(text)
     delimiters = {v: k for k, v in delimiters.items()}
     insert_at = []
-    for entity in entities:
+    for i, entity in enumerate(entities):
         s = entity.offset
         e = entity.offset + entity.length
         delimiter = delimiters.get(type(entity), None)
         if delimiter:
-            insert_at.append((s, delimiter))
-            insert_at.append((e, delimiter))
+            insert_at.append((s, i, delimiter))
+            insert_at.append((e, len(entities) - i, delimiter))
         else:
             url = None
             if isinstance(entity, MessageEntityTextUrl):
@@ -178,12 +178,12 @@ def unparse(text, entities, delimiters=None, url_fmt=None):
             elif isinstance(entity, MessageEntityMentionName):
                 url = 'tg://user?id={}'.format(entity.user_id)
             if url:
-                insert_at.append((s, '['))
-                insert_at.append((e, ']({})'.format(url)))
+                insert_at.append((s, i, '['))
+                insert_at.append((e, len(entities) - i, ']({})'.format(url)))
 
-    insert_at.sort(key=lambda t: t[0])
+    insert_at.sort(key=lambda t: (t[0], t[1]))
     while insert_at:
-        at, what = insert_at.pop()
+        at, _, what = insert_at.pop()
 
         # If we are in the middle of a surrogate nudge the position by -1.
         # Otherwise we would end up with malformed text and fail to encode.