diff --git a/backend/danswer/db/users.py b/backend/danswer/db/users.py
index 24f7dc501c7..5014c35cbec 100644
--- a/backend/danswer/db/users.py
+++ b/backend/danswer/db/users.py
@@ -103,17 +103,6 @@ def list_users(
     return db_session.scalars(stmt).unique().all()
 
 
-def get_users_by_emails(
-    db_session: Session, emails: list[str]
-) -> tuple[list[User], list[str]]:
-    # Use distinct to avoid duplicates
-    stmt = select(User).filter(User.email.in_(emails))  # type: ignore
-    found_users = list(db_session.scalars(stmt).unique().all())  # Convert to list
-    found_users_emails = [user.email for user in found_users]
-    missing_user_emails = [email for email in emails if email not in found_users_emails]
-    return found_users, missing_user_emails
-
-
 def get_user_by_email(email: str, db_session: Session) -> User | None:
     user = (
         db_session.query(User)
@@ -128,7 +117,7 @@ def fetch_user_by_id(db_session: Session, user_id: UUID) -> User | None:
     return db_session.query(User).filter(User.id == user_id).first()  # type: ignore
 
 
-def _generate_non_web_slack_user(email: str) -> User:
+def _generate_slack_user(email: str) -> User:
     fastapi_users_pw_helper = PasswordHelper()
     password = fastapi_users_pw_helper.generate()
     hashed_pass = fastapi_users_pw_helper.hash(password)
@@ -149,13 +138,29 @@ def add_slack_user_if_not_exists(db_session: Session, email: str) -> User:
             db_session.commit()
         return user
 
-    user = _generate_non_web_slack_user(email=email)
+    user = _generate_slack_user(email=email)
     db_session.add(user)
     db_session.commit()
     return user
 
 
-def _generate_non_web_permissioned_user(email: str) -> User:
+def _get_users_by_emails(
+    db_session: Session, lower_emails: list[str]
+) -> tuple[list[User], list[str]]:
+    stmt = select(User).filter(func.lower(User.email).in_(lower_emails))  # type: ignore
+    found_users = list(db_session.scalars(stmt).unique().all())  # Convert to list
+
+    # Extract found emails and convert to lowercase to avoid case sensitivity issues
+    found_users_emails = [user.email.lower() for user in found_users]
+
+    # Separate emails for users that were not found
+    missing_user_emails = [
+        email for email in lower_emails if email not in found_users_emails
+    ]
+    return found_users, missing_user_emails
+
+
+def _generate_ext_permissioned_user(email: str) -> User:
     fastapi_users_pw_helper = PasswordHelper()
     password = fastapi_users_pw_helper.generate()
     hashed_pass = fastapi_users_pw_helper.hash(password)
@@ -169,12 +174,12 @@ def _generate_non_web_permissioned_user(email: str) -> User:
 def batch_add_ext_perm_user_if_not_exists(
     db_session: Session, emails: list[str]
 ) -> list[User]:
-    emails = [email.lower() for email in emails]
-    found_users, missing_user_emails = get_users_by_emails(db_session, emails)
+    lower_emails = [email.lower() for email in emails]
+    found_users, missing_lower_emails = _get_users_by_emails(db_session, lower_emails)
 
     new_users: list[User] = []
-    for email in missing_user_emails:
-        new_users.append(_generate_non_web_permissioned_user(email=email))
+    for email in missing_lower_emails:
+        new_users.append(_generate_ext_permissioned_user(email=email))
 
     db_session.add_all(new_users)
     db_session.commit()
diff --git a/backend/ee/danswer/external_permissions/confluence/doc_sync.py b/backend/ee/danswer/external_permissions/confluence/doc_sync.py
index 18fa27ea428..be6b2f76151 100644
--- a/backend/ee/danswer/external_permissions/confluence/doc_sync.py
+++ b/backend/ee/danswer/external_permissions/confluence/doc_sync.py
@@ -228,6 +228,16 @@ def _fetch_all_page_restrictions_for_space(
                     external_access=space_permissions,
                 )
             )
+            if (
+                not space_permissions.is_public
+                and not space_permissions.external_user_emails
+                and not space_permissions.external_user_group_ids
+            ):
+                logger.warning(
+                    f"Permissions are empty for document: {slim_doc.id}\n"
+                    "This means space permissions are may be wrong for"
+                    f" Space key: {space_key}"
+                )
             continue
 
         logger.warning(f"No permissions found for document {slim_doc.id}")