diff --git a/telethon/extensions/html.py b/telethon/extensions/html.py
index 3d3b6993..9732b615 100644
--- a/telethon/extensions/html.py
+++ b/telethon/extensions/html.py
@@ -159,7 +159,7 @@ def unparse(text: str, entities: Iterable[TypeMessageEntity], _offset: int = 0,
     html = []
     last_offset = 0
     for i, entity in enumerate(entities):
-        if entity.offset > _offset + _length:
+        if entity.offset >= _offset + _length:
             break
         relative_offset = entity.offset - _offset
         if relative_offset > last_offset:
diff --git a/tests/telethon/extensions/test_html.py b/tests/telethon/extensions/test_html.py
index a6a869a4..ee497321 100644
--- a/tests/telethon/extensions/test_html.py
+++ b/tests/telethon/extensions/test_html.py
@@ -2,7 +2,7 @@
 Tests for `telethon.extensions.html`.
 """
 from telethon.extensions import html
-from telethon.tl.types import MessageEntityBold, MessageEntityTextUrl
+from telethon.tl.types import MessageEntityBold, MessageEntityItalic, MessageEntityTextUrl
 
 
 def test_entity_edges():
@@ -36,3 +36,18 @@ def test_trailing_malformed_entities():
     entities = [MessageEntityTextUrl(offset=2, length=43, url='https://example.com')]
     result = html.unparse(text, entities)
     assert result == '🏆<a href="https://example.com">Telegram Official Android Challenge is over🏆</a>'
+
+
+def test_entities_together():
+    """
+    Test that an entity followed immediately by a different one behaves well.
+    """
+    original = '<strong>⚙️</strong><em>Settings</em>'
+    stripped = '⚙️Settings'
+
+    text, entities = html.parse(original)
+    assert text == stripped
+    assert entities == [MessageEntityBold(0, 2), MessageEntityItalic(2, 8)]
+
+    text = html.unparse(text, entities)
+    assert text == original
diff --git a/tests/telethon/extensions/test_markdown.py b/tests/telethon/extensions/test_markdown.py
index f4ce0e23..2f263644 100644
--- a/tests/telethon/extensions/test_markdown.py
+++ b/tests/telethon/extensions/test_markdown.py
@@ -2,7 +2,7 @@
 Tests for `telethon.extensions.markdown`.
 """
 from telethon.extensions import markdown
-from telethon.tl.types import MessageEntityBold, MessageEntityTextUrl
+from telethon.tl.types import MessageEntityBold, MessageEntityItalic, MessageEntityTextUrl
 
 
 def test_entity_edges():
@@ -36,3 +36,18 @@ def test_trailing_malformed_entities():
     entities = [MessageEntityTextUrl(offset=2, length=43, url='https://example.com')]
     result = markdown.unparse(text, entities)
     assert result == "🏆[Telegram Official Android Challenge is over🏆](https://example.com)"
+
+
+def test_entities_together():
+    """
+    Test that an entity followed immediately by a different one behaves well.
+    """
+    original = '**⚙️**__Settings__'
+    stripped = '⚙️Settings'
+
+    text, entities = markdown.parse(original)
+    assert text == stripped
+    assert entities == [MessageEntityBold(0, 2), MessageEntityItalic(2, 8)]
+
+    text = markdown.unparse(text, entities)
+    assert text == original