diff --git a/files/classes/comment.py b/files/classes/comment.py
index 32f9b2733..e8939eb70 100644
--- a/files/classes/comment.py
+++ b/files/classes/comment.py
@@ -515,3 +515,16 @@ class Comment(Base):
 	@lazy
 	def is_effortpost(self):
 		return len(self.body) >= 1000
+
+	def pin_parents(self):
+		c = self
+		while c.level > 2:
+			c = c.parent_comment
+			c.stickied_child_id = self.id
+			g.db.add(c)
+
+	def unpin_parents(self):
+		cleanup = g.db.query(Comment).filter_by(stickied_child_id=self.id).all()
+		for c in cleanup:
+			c.stickied_child_id = None
+			g.db.add(c)
diff --git a/files/routes/awards.py b/files/routes/awards.py
index 0eb2b8dd8..cf092d803 100644
--- a/files/routes/awards.py
+++ b/files/routes/awards.py
@@ -316,10 +316,12 @@ def award_thing(v, thing_type, id):
 			obj.stickied_utc += add
 		else:
 			obj.stickied_utc = int(time.time()) + add
+			if isinstance(obj, Comment):
+				obj.pin_parents()
 
 		obj.stickied = f'{v.username}{PIN_AWARD_TEXT}'
 
-		if isinstance(obj. Post):
+		if isinstance(obj, Post):
 			cache.delete_memoized(frontlist)
 	elif kind == "unpin":
 		if not obj.stickied_utc: abort(400)
@@ -334,7 +336,10 @@ def award_thing(v, thing_type, id):
 			if time.time() > t:
 				obj.stickied = None
 				obj.stickied_utc = None
-				cache.delete_memoized(frontlist)
+				if isinstance(obj, Post):
+					cache.delete_memoized(frontlist)
+				else:
+					obj.unpin_parents()	
 			else: obj.stickied_utc = t
 	elif kind == "queen":
 		if not author.queen:
diff --git a/files/routes/comments.py b/files/routes/comments.py
index a5d1eaee0..a92f5b96f 100644
--- a/files/routes/comments.py
+++ b/files/routes/comments.py
@@ -443,10 +443,13 @@ def delete_comment(cid, v):
 		if c.author_id != v.id: abort(403)
 
 		c.deleted_utc = int(time.time())
-		c.stickied = None
-		c.stickied_utc = None
 		g.db.add(c)
 
+		if c.stickied:
+			c.stickied = None
+			c.stickied_utc = None
+			c.unpin_parents()
+
 		if not (c.parent_post in ADMIGGER_THREADS and c.level == 1):
 			v.comment_count -= 1
 			g.db.add(v)
@@ -509,6 +512,8 @@ def pin_comment(cid, v):
 
 		g.db.add(comment)
 
+		comment.pin_parents()
+
 		if v.id != comment.author_id:
 			if comment.post.ghost: message = f"OP has pinned your [comment]({comment.shortlink})"
 			else: message = f"@{v.username} (OP) has pinned your [comment]({comment.shortlink})"
@@ -537,6 +542,8 @@ def unpin_comment(cid, v):
 		comment.stickied_utc = None
 		g.db.add(comment)
 
+		comment.unpin_parents()
+
 		if v.id != comment.author_id:
 			message = f"@{v.username} (OP) has unpinned your [comment]({comment.shortlink})"
 			send_repeatable_notification(comment.author_id, message)
diff --git a/files/routes/holes.py b/files/routes/holes.py
index bd7e80ab0..0a55a0b31 100644
--- a/files/routes/holes.py
+++ b/files/routes/holes.py
@@ -852,6 +852,8 @@ def pin_comment_mod(cid, v):
 
 		g.db.add(comment)
 
+		comment.pin_parents()
+
 		ma = HoleAction(
 			hole=comment.post.hole,
 			kind="pin_comment",
@@ -883,6 +885,8 @@ def unpin_comment_mod(cid, v):
 		comment.stickied_utc = None
 		g.db.add(comment)
 
+		comment.unpin_parents()
+
 		ma = HoleAction(
 			hole=comment.post.hole,
 			kind="unpin_comment",