diff --git a/print_service/models/__init__.py b/print_service/models/__init__.py
index d1ffcfe..9852ee0 100644
--- a/print_service/models/__init__.py
+++ b/print_service/models/__init__.py
@@ -23,8 +23,10 @@ class UnionMember(Model):
     union_number: Mapped[str] = mapped_column(String, nullable=True)
     student_number: Mapped[str] = mapped_column(String, nullable=True)
 
-    files: Mapped[list[File]] = relationship('File', back_populates='owner')
-    print_facts: Mapped[list[PrintFact]] = relationship('PrintFact', back_populates='owner')
+    files: Mapped[list[File]] = relationship('File', back_populates='owner', lazy="joined")
+    print_facts: Mapped[list[PrintFact]] = relationship(
+        'PrintFact', back_populates='owner', lazy="joined"
+    )
 
 
 class File(Model):
diff --git a/print_service/routes/user.py b/print_service/routes/user.py
index c8098f9..0b9c646 100644
--- a/print_service/routes/user.py
+++ b/print_service/routes/user.py
@@ -10,7 +10,7 @@
 
 from print_service import __version__
 from print_service.exceptions import UnionStudentDuplicate, UserNotFound
-from print_service.models import UnionMember
+from print_service.models import File, PrintFact, UnionMember
 from print_service.schema import BaseModel
 from print_service.settings import get_settings
 
@@ -90,7 +90,7 @@ def update_list(
         set(student_numbers)
     ):
         raise UnionStudentDuplicate()
-
+    users_id = []
     for user in input.users:
         db_user: UnionMember = (
             db.session.query(UnionMember)
@@ -108,21 +108,29 @@ def update_list(
             )
             .one_or_none()
         )
-
         if db_user:
             db_user.surname = user.username
             db_user.union_number = user.union_number
             db_user.student_number = user.student_number
         else:
             db.session.add(
-                UnionMember(
+                db_user := UnionMember(
                     surname=user.username,
                     union_number=user.union_number,
                     student_number=user.student_number,
                 )
             )
         db.session.flush()
-
+        users_id.append(db_user.id)
+    db_delete_users: list[UnionMember] = (
+        db.session.query(UnionMember).filter(UnionMember.id.notin_(users_id)).all()
+    )
+    for _user in db_delete_users:
+        for print_fact in _user.print_facts:
+            db.session.delete(print_fact)
+        for files in _user.files:
+            db.session.delete(files)
+        db.session.delete(_user)
     db.session.commit()
     return {"status": "ok", "count": len(input.users)}
 
diff --git a/tests/test_routes/test_user.py b/tests/test_routes/test_user.py
index 97fdb44..0900236 100644
--- a/tests/test_routes/test_user.py
+++ b/tests/test_routes/test_user.py
@@ -88,3 +88,105 @@ def test_post_list_duplicates(users, client):
     body = {'users': users}
     res = client.post(url, json=body)
     assert res.status_code == status.HTTP_400_BAD_REQUEST, res.json()
+
+
+def test_post_delete(client):
+    body = {
+        'users': [
+            {
+                'username': 'paul',
+                'union_number': '1966',
+                'student_number': '1967',
+            }
+        ],
+    }
+    params = {
+        'surname': 'paul',
+        'number': '1966',
+    }
+    res_post = client.post(url, json=body)
+    assert res_post.status_code == status.HTTP_200_OK
+    res_get1 = client.get(url, params=params)
+    assert res_get1.status_code == status.HTTP_202_ACCEPTED
+    res_post_delete = client.post(url, json={'users': []})
+    assert res_post_delete.status_code == status.HTTP_200_OK
+    res_get2 = client.get(url, params=params)
+    assert res_get2.status_code == status.HTTP_404_NOT_FOUND
+    body = {
+        'users': [
+            {
+                'username': 'paul',
+                'union_number': '1966',
+                'student_number': '1967',
+            },
+            {
+                'username': 'semen',
+                'union_number': '1888',
+                'student_number': '1887',
+            },
+            {
+                'username': 'artem',
+                'union_number': '1777',
+                'student_number': '1776',
+            },
+        ],
+    }
+    res_post = client.post(url, json=body)
+    assert res_post.status_code == status.HTTP_200_OK
+    params = {
+        'surname': 'semen',
+        'number': '1888',
+    }
+    res_get = client.get(url, params=params)
+    assert res_get.status_code == status.HTTP_202_ACCEPTED
+    params = {
+        'surname': 'artem',
+        'number': '1777',
+    }
+    res_get = client.get(url, params=params)
+    assert res_get.status_code == status.HTTP_202_ACCEPTED
+    body = {
+        'users': [
+            {
+                'username': 'semen',
+                'union_number': '1889',
+                'student_number': '1887',
+            },
+            {
+                'username': 'artem',
+                'union_number': '1777',
+                'student_number': '1776',
+            },
+            {
+                'username': 'roman',
+                'union_number': '1999',
+                'student_number': '1998',
+            },
+        ],
+    }
+    res_post_multi = client.post(url, json=body)
+    assert res_post_multi.status_code == status.HTTP_200_OK
+    params = {
+        'surname': 'semen',
+        'number': '1888',
+    }
+    res_get = client.get(url, params=params)
+    assert res_get.status_code == status.HTTP_404_NOT_FOUND
+    params = {
+        'surname': 'semen',
+        'number': '1889',
+    }
+    res_get = client.get(url, params=params)
+    assert res_get.status_code == status.HTTP_202_ACCEPTED
+    params = {
+        'surname': 'artem',
+        'number': '1777',
+    }
+    res_get = client.get(url, params=params)
+    assert res_get.status_code == status.HTTP_202_ACCEPTED
+    params = {
+        'surname': 'roman',
+        'number': '1999',
+    }
+    res_get = client.get(url, params=params)
+    assert res_get.status_code == status.HTTP_202_ACCEPTED