diff --git a/openbook_communities/helpers.py b/openbook_communities/helpers.py
index faf081ed0eebb21213de11e3c24d96f1729524e9..8e413d1ba20f1dc442b20d8866be3638b4199fe6 100644
--- a/openbook_communities/helpers.py
+++ b/openbook_communities/helpers.py
@@ -32,11 +32,20 @@ def upload_to_community_cover_directory(community, filename):
     )
 
 
+def upload_to_community_tool_thumbnail_directory(tool, filename):
+    return create_upload_filename(
+        username=tool.community.creator.username,
+        object_type="community_tool_thumbnail",
+        object_id=tool.id,
+        filename=filename,
+    )
+
+
 def upload_to_community_task_thumbnail_directory(task, filename):
     return create_upload_filename(
         username=task.community.creator.username,
         object_type="community_task_thumbnail",
-        object_id=task.community.id,
+        object_id=task.id,
         filename=filename,
     )
 
diff --git a/openbook_communities/migrations/0042_alter_collaborationtool_thumbnail.py b/openbook_communities/migrations/0042_alter_collaborationtool_thumbnail.py
new file mode 100644
index 0000000000000000000000000000000000000000..3a9003038ce4ad49af736d8642d7ad06464669e7
--- /dev/null
+++ b/openbook_communities/migrations/0042_alter_collaborationtool_thumbnail.py
@@ -0,0 +1,26 @@
+# Generated by Django 5.0.8 on 2025-02-04 15:33
+
+import imagekit.models.fields
+import openbook_communities.helpers
+from django.db import migrations
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ("openbook_communities", "0041_alter_community_name_alter_community_title"),
+    ]
+
+    operations = [
+        migrations.AlterField(
+            model_name="collaborationtool",
+            name="thumbnail",
+            field=imagekit.models.fields.ProcessedImageField(
+                blank=True,
+                max_length=500,
+                null=True,
+                upload_to=openbook_communities.helpers.upload_to_community_tool_thumbnail_directory,
+                verbose_name="thumbnail",
+            ),
+        ),
+    ]
diff --git a/openbook_communities/models/__init__.py b/openbook_communities/models/__init__.py
index 2b07eebec6510af08bb206de2c79d07c697ed655..1806bcce0390adc4db7bbe5af42452278b22cce9 100644
--- a/openbook_communities/models/__init__.py
+++ b/openbook_communities/models/__init__.py
@@ -43,6 +43,7 @@ from openbook_communities.helpers import (
     upload_to_community_avatar_directory,
     upload_to_community_cover_directory,
     upload_to_community_task_thumbnail_directory,
+    upload_to_community_tool_thumbnail_directory,
 )
 from openbook_communities.queries import (
     make_search_communities_query_for_user,
@@ -1539,7 +1540,7 @@ class CollaborationTool(ModelWithUUID):
         verbose_name=_("thumbnail"),
         blank=True,
         null=True,
-        upload_to=upload_to_community_task_thumbnail_directory,
+        upload_to=upload_to_community_tool_thumbnail_directory,
         processors=[
             ExifRotate(),
             ResizeToFit(