diff --git a/odoo/addons/test_http/controllers.py b/odoo/addons/test_http/controllers.py
index 9933c0862f6..dba5f5299e1 100644
--- a/odoo/addons/test_http/controllers.py
+++ b/odoo/addons/test_http/controllers.py
@@ -1,7 +1,11 @@
 # Part of Odoo. See LICENSE file for full copyright and licensing details.
 import json
 import logging
+
 import werkzeug
+from psycopg2.errorcodes import SERIALIZATION_FAILURE
+from psycopg2 import OperationalError
+
 from odoo import http
 from odoo.exceptions import AccessError, UserError
 from odoo.http import request
@@ -16,6 +20,14 @@ CT_JSON = {'Content-Type': 'application/json; charset=utf-8'}
 WSGI_SAFE_KEYS = {'PATH_INFO', 'QUERY_STRING', 'RAW_URI', 'SCRIPT_NAME', 'wsgi.url_scheme'}
 
 
+# Force serialization errors. Patched in some tests.
+should_fail = None
+
+
+class SerializationFailureError(OperationalError):
+    pgcode = SERIALIZATION_FAILURE
+
+
 class TestHttp(http.Controller):
 
     # =====================================================
@@ -177,3 +189,16 @@ class TestHttp(http.Controller):
                 raise AccessError("Wrong iris code")
             if error == 'UserError':
                 raise UserError("Walter is AFK")
+
+    @http.route("/test_http/upload_file", methods=["POST"], type="http", auth="none", csrf=False)
+    def upload_file_retry(self, ufile):
+        global should_fail  # pylint: disable=W0603
+        if should_fail is None:
+            raise ValueError("should_fail should be set.")
+
+        data = ufile.read()
+        if should_fail:
+            should_fail = False  # Fail once
+            raise SerializationFailureError()
+
+        return data.decode()
diff --git a/odoo/addons/test_http/tests/test_misc.py b/odoo/addons/test_http/tests/test_misc.py
index 577bafd2907..2efddb9f8e0 100644
--- a/odoo/addons/test_http/tests/test_misc.py
+++ b/odoo/addons/test_http/tests/test_misc.py
@@ -1,6 +1,7 @@
 # Part of Odoo. See LICENSE file for full copyright and licensing details.
 
 import json
+from io import StringIO
 from socket import gethostbyname
 from unittest.mock import patch
 from urllib.parse import urlparse
@@ -127,6 +128,13 @@ class TestHttpMisc(TestHttpBase):
                 'time_zone': 'Europe/Paris',
             })
 
+    def test_misc6_upload_file_retry(self):
+        from odoo.addons.test_http import controllers  # pylint: disable=C0415
+
+        with patch.object(controllers, "should_fail", True), StringIO("Hello world!") as file:
+            res = self.url_open("/test_http/upload_file", files={"ufile": file}, timeout=None)
+            self.assertEqual(res.status_code, 200)
+            self.assertEqual(res.text, file.getvalue())
 
 @tagged('post_install', '-at_install')
 class TestHttpCors(TestHttpBase):
diff --git a/odoo/service/model.py b/odoo/service/model.py
index e368d5bfcf1..c31a14977d5 100644
--- a/odoo/service/model.py
+++ b/odoo/service/model.py
@@ -142,6 +142,12 @@ def retrying(func, env):
                 env.registry.reset_changes()
                 if request:
                     request.session = request._get_session_and_dbname()[0]
+                    # Rewind files in case of failure
+                    for filename, file in request.httprequest.files.items():
+                        if hasattr(file, "seekable") and file.seekable():
+                            file.seek(0)
+                        else:
+                            raise RuntimeError(f"Cannot retry request on input file {filename!r} after serialization failure") from exc
                 if isinstance(exc, IntegrityError):
                     raise _as_validation_error(env, exc) from exc
                 if exc.pgcode not in PG_CONCURRENCY_ERRORS_TO_RETRY: