diff --git a/stdplugins/markdown.py b/stdplugins/markdown.py
index 976c936..bee0372 100644
--- a/stdplugins/markdown.py
+++ b/stdplugins/markdown.py
@@ -57,7 +57,7 @@ PARSED_ENTITIES = (
     MessageEntityBold, MessageEntityItalic, MessageEntityCode,
     MessageEntityPre, MessageEntityTextUrl
 )
-# a matcher is a tuple of (regex pattern, parse function)
+# A matcher is a tuple of (regex pattern, parse function)
 # where the parse function takes the match and returns (text, entity)
 MATCHERS = [
     (DEFAULT_URL_RE, parse_url_match),
@@ -72,16 +72,21 @@ MATCHERS = [
 
 def parse(message, old_entities=None):
     entities = []
-    old_entities = {e.offset: e for e in old_entities or []}
+    old_entities = sorted(old_entities or [], key=lambda e: e.offset)
 
     i = 0
+    after = 0
     message = _add_surrogate(message)
     while i < len(message):
-        # skip already existing entities if we're at one
-        if i in old_entities:
-            i += old_entities[i].length
+        for after, e in enumerate(old_entities[after:], start=after):
+            # If the next entity is strictly to our right, we're done here
+            if i < e.offset:
+                break
+            # Skip already existing entities if we're at one
+            if i == e.offset:
+                i += e.length
 
-        # find the first pattern that matches
+        # Find the first pattern that matches
         for pattern, parser in MATCHERS:
             match = pattern.match(message, pos=i)
             if match:
@@ -92,30 +97,27 @@ def parse(message, old_entities=None):
 
         text, entity = parser(match)
 
-        # shift old entities after our current position (so they stay in place)
-        shift = len(text) - len(message[match.start():match.end()])
+        # Shift old entities after our current position (so they stay in place)
+        shift = len(text) - len(match[0])
         if shift:
-            old_entities = old_entities.values()
-            for entity in old_entities:
-                if entity.offset >= i:
-                    entity.offset += shift
-            old_entities = {e.offset: e for e in old_entities}
+            for e in old_entities[after:]:
+                e.offset += shift
 
-        # replace whole match with text from parser
+        # Replace whole match with text from parser
         message = ''.join((
             message[:match.start()],
             text,
             message[match.end():]
         ))
 
-        # append entity if we got one
+        # Append entity if we got one
         if entity:
             entities.append(entity)
 
-        # skip past the match
+        # Skip past the match
         i += len(text)
 
-    return _del_surrogate(message), entities + list(old_entities.values())
+    return _del_surrogate(message), entities + old_entities
 
 
 @borg.on(events.MessageEdited(outgoing=True))