diff --git a/spire/journal/actions.py b/spire/journal/actions.py
index d3dc68d..d86bd45 100644
--- a/spire/journal/actions.py
+++ b/spire/journal/actions.py
@@ -11,6 +11,7 @@
 from uuid import UUID, uuid4
 
 import boto3
+import requests
 
 from sqlalchemy.orm import Session, Query
 from sqlalchemy import or_, func, text, and_
@@ -585,6 +586,27 @@ async def get_journal_entries(
     return query.all()
 
 
+async def delete_entry_images(
+    access_token: str, journal_spec: JournalSpec, entry_id: UUID
+) -> None:
+    images_url = f"https://files.bugout.dev/files/{str(journal_spec.id)}/entries/{str(entry_id)}/images"
+    headers = {"Authorization": f"Bearer {access_token}"}
+    images_response = requests.get(images_url, headers=headers, timeout=4)
+    images_response.raise_for_status()
+    images = images_response.json()
+
+    for image in images.images:
+        try:
+            r = requests.delete(
+                f"{images_url}/{image['id']}", headers=headers, timeout=4
+            )
+            r.raise_for_status()
+        except Exception as e:
+            logger.error(
+                f"Unable to delete image with id: {image['id']} for entry with id: {str(entry_id)}"
+            )
+
+
 async def delete_journal_entry(
     db_session: Session,
     journal_spec: JournalSpec,
diff --git a/spire/journal/api.py b/spire/journal/api.py
index aacdba1..8761458 100644
--- a/spire/journal/api.py
+++ b/spire/journal/api.py
@@ -1405,6 +1405,8 @@ async def delete_entry(
         {JournalEntryScopes.DELETE},
     )
 
+    access_token = request.state.token
+
     journal_spec = JournalSpec(id=journal_id, bugout_user_id=request.state.user_id)
     try:
         journal = await actions.find_journal(
@@ -1422,6 +1424,11 @@ async def delete_entry(
         raise HTTPException(status_code=500)
     es_index = journal.search_index
 
+    try:
+        await actions.delete_entry_images(access_token, journal_spec, entry_id)
+    except Exception as e:
+        logger.error(f"Error due deleting entry images: {str(e)}")
+
     try:
         journal_entry = await actions.delete_journal_entry(
             db_session,