diff --git a/edi_oca/models/edi_backend.py b/edi_oca/models/edi_backend.py
index 427c435d61..994aac20e2 100644
--- a/edi_oca/models/edi_backend.py
+++ b/edi_oca/models/edi_backend.py
@@ -8,6 +8,7 @@
 import base64
 import logging
 import traceback
+from datetime import timedelta
 from io import StringIO
 
 from odoo import _, exceptions, fields, models, tools
@@ -322,10 +323,20 @@ def exchange_send(self, exchange_record):
             _logger.debug("%s sent", exchange_record.identifier)
         except self._send_retryable_exceptions() as err:
             error = _get_exception_msg()
-            _logger.debug("%s send failed. To be retried.", exchange_record.identifier)
-            raise RetryableJobError(
-                error, **exchange_record._job_retry_params()
-            ) from err
+            if self._send_should_retry(exchange_record):
+                _logger.debug(
+                    "%s send failed. To be retried.", exchange_record.identifier
+                )
+                raise RetryableJobError(
+                    error, **exchange_record._job_retry_params()
+                ) from err
+            else:
+                state = "output_error_on_send"
+                message = exchange_record._exchange_status_message("send_ko")
+                res = f"Error: {error}"
+                _logger.debug(
+                    "%s send failed. Marked as errored.", exchange_record.identifier
+                )
         except self._swallable_exceptions():
             if self.env.context.get("_edi_send_break_on_error"):
                 raise
@@ -374,6 +385,10 @@ def _send_retryable_exceptions(self):
         # when dealing w/ internal or external systems or filesystems
         return (IOError, OSError)
 
+    def _send_should_retry(self, exc_record):
+        # Safety check not to retry indefinitely
+        return exc_record.create_date >= (fields.Datetime.now() - timedelta(days=1))
+
     def _output_check_send(self, exchange_record):
         if exchange_record.direction != "output":
             raise exceptions.UserError(
diff --git a/edi_oca/tests/test_backend_jobs.py b/edi_oca/tests/test_backend_jobs.py
index b33eb1fbbd..f74a832588 100644
--- a/edi_oca/tests/test_backend_jobs.py
+++ b/edi_oca/tests/test_backend_jobs.py
@@ -3,6 +3,7 @@
 # License AGPL-3.0 or later (http://www.gnu.org/licenses/agpl).
 
 import mock
+from freezegun import freeze_time
 from requests.exceptions import ConnectionError as ReqConnectionError
 
 from odoo.addons.queue_job.exception import RetryableJobError
@@ -75,6 +76,38 @@ def test_output_fail_retry(self):
             mocked.side_effect = ReqConnectionError("Connection broken")
             with self.assertRaises(RetryableJobError):
                 job.perform()
+        self.assertEqual(record.edi_exchange_state, "output_pending")
+
+    def test_output_fail_too_many_retries(self):
+        job_counter = self.job_counter()
+        vals = {
+            "model": self.partner._name,
+            "res_id": self.partner.id,
+            "edi_exchange_state": "output_pending",
+        }
+        record = self.backend.create_record("test_csv_output", vals)
+        record._write({"create_date": "2024-01-10 09:00:00"})
+        record._set_file_content("ABC")
+        with mock.patch.object(type(self.backend), "_exchange_send") as mocked:
+            mocked.side_effect = ReqConnectionError("Connection broken")
+            with freeze_time("2024-01-10 11:00:00"):
+                # + 2 hours
+                job = self.backend.with_delay().exchange_send(record)
+                with self.assertRaises(RetryableJobError):
+                    job.perform()
+            with freeze_time("2024-01-11 08:50:00"):
+                # + 23 hours and 50 minutes
+                job = self.backend.with_delay().exchange_send(record)
+                with self.assertRaises(RetryableJobError):
+                    job.perform()
+            self.assertEqual(record.edi_exchange_state, "output_pending")
+            with freeze_time("2024-01-11 09:20:00"):
+                # + 24 hours and 20 minutes
+                job = self.backend.with_delay().exchange_send(record)
+                res = job.perform()
+            self.assertIn("Error", res)
+        job_counter.search_created()
+        self.assertEqual(record.edi_exchange_state, "output_error_on_send")
 
     def test_input(self):
         job_counter = self.job_counter()