diff --git a/addons/mail/tests/test_ir_mail_server.py b/addons/mail/tests/test_ir_mail_server.py
index 7137951bd9c..aef82d0c516 100644
--- a/addons/mail/tests/test_ir_mail_server.py
+++ b/addons/mail/tests/test_ir_mail_server.py
@@ -225,7 +225,7 @@ class TestIrMailServer(MailCommon):
                 self.assertEqual(mail_server, expected_mail_server)
                 self.assertEqual(mail_from, expected_email_from)
 
-    @mute_logger('odoo.models.unlink')
+    @mute_logger('odoo.models.unlink', 'odoo.addons.base.models.ir_mail_server')
     def test_mail_server_send_email(self):
         """ Test main 'send_email' usage: check mail_server choice based on from
         filters, encapsulation, spoofing. """
@@ -292,3 +292,19 @@ class TestIrMailServer(MailCommon):
                 message_from=f'"Name" <{self.default_from}@{self.alias_domain}>',
                 mail_server=self.mail_server_domain,
             )
+
+        # miss-configured database, no mail servers from filter
+        # match the user / notification email
+        self.env['ir.mail_server'].search([]).from_filter = "random.domain"
+        self.mail_alias_domain.default_from = 'test'
+        self.mail_alias_domain.name = 'custom_domain.com'
+        with self.mock_smtplib_connection():
+            message = self._build_email(mail_from='specific_user@test.com')
+            IrMailServer.send_email(message)
+
+        self.connect_mocked.assert_called_once()
+        self.assertSMTPEmailsSent(
+            smtp_from='test@custom_domain.com',
+            message_from='"specific_user" <test@custom_domain.com>',
+            from_filter='random.domain',
+        )
diff --git a/odoo/addons/base/models/ir_mail_server.py b/odoo/addons/base/models/ir_mail_server.py
index 3704a2c6fcb..d76fab25d02 100644
--- a/odoo/addons/base/models/ir_mail_server.py
+++ b/odoo/addons/base/models/ir_mail_server.py
@@ -748,13 +748,17 @@ class IrMailServer(models.Model):
 
         # 3. Take the first mail server without "from_filter" because
         # nothing else has been found... Will spoof the FROM because
-        # we have no other choices
+        # we have no other choices (will use the notification email if available
+        # otherwise we will use the user email)
         if mail_server := mail_servers.filtered(lambda m: not m.from_filter):
-            return mail_server[0], email_from
+            return mail_server[0], notifications_email or email_from
 
         # 4. Return the first mail server even if it was configured for another domain
         if mail_servers:
-            return mail_servers[0], email_from
+            _logger.warning(
+                "No mail server matches the from_filter, using %s as fallback",
+                notifications_email or email_from)
+            return mail_servers[0], notifications_email or email_from
 
         # 5: SMTP config in odoo-bin arguments
         from_filter = self.env['ir.mail_server']._get_default_from_filter()
@@ -765,7 +769,11 @@ class IrMailServer(models.Model):
         if notifications_email and self._match_from_filter(notifications_email, from_filter):
             return None, notifications_email
 
-        return None, email_from
+        _logger.warning(
+            "The from filter of the CLI configuration does not match the notification email "
+            "or the user email, using %s as fallback",
+            notifications_email or email_from)
+        return None, notifications_email or email_from
 
     @api.model
     def _match_from_filter(self, email_from, from_filter):
diff --git a/odoo/addons/base/tests/test_ir_mail_server.py b/odoo/addons/base/tests/test_ir_mail_server.py
index 1b51499cb23..39fb966d892 100644
--- a/odoo/addons/base/tests/test_ir_mail_server.py
+++ b/odoo/addons/base/tests/test_ir_mail_server.py
@@ -287,7 +287,7 @@ class TestIrMailServer(TransactionCase, MockSmtplibCase):
                 from_filter=False,
             )
 
-    @mute_logger('odoo.models.unlink')
+    @mute_logger('odoo.models.unlink', 'odoo.addons.base.models.ir_mail_server')
     def test_mail_server_send_email_context_force(self):
         """ Allow to force notifications_email / bounce_address from context
         to allow higher-level apps to send values until end of mail stack
@@ -317,6 +317,20 @@ class TestIrMailServer(TransactionCase, MockSmtplibCase):
             from_filter=context_server.from_filter,
         )
 
+        # miss-configured database, no mail servers from filter
+        # match the user / notification email
+        self.env['ir.mail_server'].search([]).from_filter = "random.domain"
+        with self.mock_smtplib_connection():
+            message = self._build_email(mail_from='specific_user@test.com')
+            IrMailServer.with_context(domain_notifications_email='test@custom_domain.com').send_email(message)
+
+        self.connect_mocked.assert_called_once()
+        self.assertSMTPEmailsSent(
+            smtp_from='test@custom_domain.com',
+            message_from='"specific_user" <test@custom_domain.com>',
+            from_filter='random.domain',
+        )
+
     @mute_logger('odoo.models.unlink')
     def test_mail_server_send_email_IDNA(self):
         """ Test that the mail from / recipient envelop are encoded using IDNA """
@@ -332,7 +346,7 @@ class TestIrMailServer(TransactionCase, MockSmtplibCase):
             from_filter=False,
         )
 
-    @mute_logger('odoo.models.unlink')
+    @mute_logger('odoo.models.unlink', 'odoo.addons.base.models.ir_mail_server')
     @patch.dict(config.options, {
         "from_filter": "dummy@example.com, test.mycompany.com, dummy2@example.com",
         "smtp_server": "example.com",