diff --git a/migrations/sql/V2023.10.06.10.36__add_now_submissions_document_delete_ind.sql b/migrations/sql/V2023.10.06.10.36__add_now_submissions_document_delete_ind.sql
new file mode 100644
index 0000000000..dbb5c3d299
--- /dev/null
+++ b/migrations/sql/V2023.10.06.10.36__add_now_submissions_document_delete_ind.sql
@@ -0,0 +1,4 @@
+ALTER TABLE
+    now_submissions.document
+ADD
+    COLUMN IF NOT EXISTS deleted_ind boolean DEFAULT false NOT NULL;
\ No newline at end of file
diff --git a/services/core-api/app/api/now_applications/resources/now_application_document_resource.py b/services/core-api/app/api/now_applications/resources/now_application_document_resource.py
index fa47ebd0ab..316f29d675 100644
--- a/services/core-api/app/api/now_applications/resources/now_application_document_resource.py
+++ b/services/core-api/app/api/now_applications/resources/now_application_document_resource.py
@@ -16,6 +16,7 @@
 from app.api.now_applications.models.now_application_document_identity_xref import NOWApplicationDocumentIdentityXref
 from app.api.utils.custom_reqparser import CustomReqparser
 from app.api.mines.response_models import MINE_DOCUMENT_MODEL
+from app.api.now_submissions.models.document import Document
 
 
 class NOWApplicationDocumentUploadResource(Resource, UserMixin):
@@ -83,8 +84,8 @@ class NOWApplicationDocumentResource(Resource, UserMixin):
     @requires_role_edit_permit
     def delete(self, application_guid, mine_document_guid):
         mine_document = MineDocument.find_by_mine_document_guid(mine_document_guid)
-        now_app_doc_xref_exists = mine_document.now_application_document_xref is not None
-        now_app_doc_id_xref_exists = mine_document.now_application_document_identity_xref is not None
+        now_app_doc_xref_exists = mine_document and mine_document.now_application_document_xref is not None
+        now_app_doc_id_xref_exists = mine_document and mine_document.now_application_document_identity_xref is not None
 
         if not mine_document or (now_app_doc_xref_exists 
                                  and application_guid != str(
@@ -106,6 +107,13 @@ def delete(self, application_guid, mine_document_guid):
         if now_app_doc_xref_exists:
             mine_document.now_application_document_xref.delete(True)
         elif now_app_doc_id_xref_exists:
+            now_submission_document = Document.find_by_messageid_and_filename(
+                mine_document.now_application_document_identity_xref.messageid,
+                mine_document.now_application_document_identity_xref.filename
+            )
+
+            if now_submission_document is not None:
+                now_submission_document.delete(True)
             mine_document.now_application_document_identity_xref.delete(True)
 
         return None, 204
diff --git a/services/core-api/app/api/now_submissions/models/document.py b/services/core-api/app/api/now_submissions/models/document.py
index 10173e5364..9b0553431f 100644
--- a/services/core-api/app/api/now_submissions/models/document.py
+++ b/services/core-api/app/api/now_submissions/models/document.py
@@ -1,12 +1,12 @@
 from sqlalchemy.schema import FetchedValue
 
-from app.api.utils.models_mixins import Base
+from app.api.utils.models_mixins import Base, SoftDeleteMixin
 from app.extensions import db
 from sqlalchemy.dialects.postgresql import UUID
 from app.api.constants import *
 
 
-class Document(Base):
+class Document(SoftDeleteMixin, Base):
     __tablename__ = "document"
     __table_args__ = {"schema": "now_submissions"}
     _edit_groups = [NOW_APPLICATION_EDIT_GROUP]
@@ -23,4 +23,11 @@ def __repr__(self):
 
     @classmethod
     def find_by_id(cls, id):
-        return cls.query.filter_by(id=id).one_or_none()
\ No newline at end of file
+        return cls.query.filter_by(id=id).one_or_none()
+    
+    @classmethod
+    def find_by_messageid_and_filename(cls, messageid, filename):
+        return cls.query.filter_by(messageid=messageid, filename=filename).first()
+    
+    def delete(self, commit=True):
+        super(Document, self).delete(commit)
\ No newline at end of file