diff --git a/addons/sale/__init__.py b/addons/sale/__init__.py
index b91ad4c9d06..a67265753e7 100644
--- a/addons/sale/__init__.py
+++ b/addons/sale/__init__.py
@@ -6,3 +6,13 @@ from . import controllers
 from . import report
 from . import wizard
 from . import populate
+
+from odoo.api import Environment, SUPERUSER_ID
+
+
+def _synchronize_cron(cr, registry):
+    env = Environment(cr, SUPERUSER_ID, {'active_test': False})
+    send_invoice_cron = env.ref('sale.send_invoice_cron', raise_if_not_found=False)
+    if send_invoice_cron:
+        config = env['ir.config_parameter'].get_param('sale.automatic_invoice', False)
+        send_invoice_cron.active = bool(config)
diff --git a/addons/sale/__manifest__.py b/addons/sale/__manifest__.py
index 94035204a25..ddc91098081 100644
--- a/addons/sale/__manifest__.py
+++ b/addons/sale/__manifest__.py
@@ -72,5 +72,6 @@ This module contains all the common features of Sales Management and eCommerce.
             'sale/static/tests/sales_team_dashboard_tests.js',
         ],
     },
+    'post_init_hook': '_synchronize_cron',
     'license': 'LGPL-3',
 }
diff --git a/addons/sale/data/sale_data.xml b/addons/sale/data/sale_data.xml
index 0f3abd5937b..8c7037993fb 100644
--- a/addons/sale/data/sale_data.xml
+++ b/addons/sale/data/sale_data.xml
@@ -16,5 +16,17 @@
             <field name="key">sale.default_confirmation_template</field>
             <field name="value" ref="sale.mail_template_sale_confirmation"/>
         </record>
+
+        <record model="ir.cron" id="send_invoice_cron">
+            <field name="name">automatic invoicing: send ready invoice</field>
+            <field name="model_id" ref="payment.model_payment_transaction" />
+            <field name="state">code</field>
+            <field name="code">model._cron_send_invoice()</field>
+            <field name="user_id" ref="base.user_root" />
+            <field name="interval_number">1</field>
+            <field name="interval_type">days</field>
+            <field name="numbercall">-1</field>
+        </record>
+
     </data>
 </odoo>
diff --git a/addons/sale/models/account_move.py b/addons/sale/models/account_move.py
index 3552fe478f8..c854192372a 100644
--- a/addons/sale/models/account_move.py
+++ b/addons/sale/models/account_move.py
@@ -109,3 +109,19 @@ class AccountMove(models.Model):
         for (order, name) in todo:
             order.message_post(body=_("Invoice %s paid", name))
         return res
+
+    def _get_invoice_delivery_partner_id(self):
+        # OVERRIDE
+        self.ensure_one()
+        return self.partner_shipping_id.id or super(AccountMove, self)._get_invoice_delivery_partner_id()
+
+    def _action_invoice_ready_to_be_sent(self):
+        # OVERRIDE
+        # Make sure the send invoice CRON is called when an invoice becomes ready to be sent by mail.
+        res = super()._action_invoice_ready_to_be_sent()
+
+        send_invoice_cron = self.env.ref('sale.send_invoice_cron', raise_if_not_found=False)
+        if send_invoice_cron:
+            send_invoice_cron._trigger()
+
+        return res
diff --git a/addons/sale/models/payment_transaction.py b/addons/sale/models/payment_transaction.py
index f7e5d83c5a4..efaf2de2545 100644
--- a/addons/sale/models/payment_transaction.py
+++ b/addons/sale/models/payment_transaction.py
@@ -3,6 +3,9 @@
 import logging
 import re
 
+from datetime import datetime
+from dateutil import relativedelta
+
 from odoo import api, fields, models, _, SUPERUSER_ID
 from odoo.tools import float_compare
 
@@ -98,17 +101,46 @@ class PaymentTransaction(models.Model):
         self._invoice_sale_orders()
         res = super()._reconcile_after_done()
         if self.env['ir.config_parameter'].sudo().get_param('sale.automatic_invoice') and any(so.state in ('sale', 'done') for so in self.sale_order_ids):
-            default_template = self.env['ir.config_parameter'].sudo().get_param('sale.default_invoice_email_template')
-            if default_template:
-                for trans in self.filtered(lambda t: t.sale_order_ids.filtered(lambda so: so.state in ('sale', 'done'))):
-                    trans = trans.with_company(trans.acquirer_id.company_id).with_context(
-                        mark_invoice_as_sent=True,
-                        company_id=trans.acquirer_id.company_id.id,
-                    )
-                    for invoice in trans.invoice_ids.with_user(SUPERUSER_ID):
-                        invoice.message_post_with_template(int(default_template), email_layout_xmlid="mail.mail_notification_paynow")
+            self.filtered(lambda t: t.sale_order_ids.filtered(lambda so: so.state in ('sale', 'done')))._send_invoice()
         return res
 
+    def _send_invoice(self):
+        default_template = self.env['ir.config_parameter'].sudo().get_param('sale.default_invoice_email_template')
+        if not default_template:
+            return
+
+        for trans in self:
+            trans = trans.with_company(trans.acquirer_id.company_id).with_context(
+                company_id=trans.acquirer_id.company_id.id,
+            )
+            invoice_to_send = trans.invoice_ids.filtered(
+                lambda i: not i.is_move_sent and i.state == 'posted' and i._is_ready_to_be_sent()
+            )
+            invoice_to_send.is_move_sent = True # Mark invoice as sent
+            for invoice in invoice_to_send.with_user(SUPERUSER_ID):
+                invoice.message_post_with_template(int(default_template), email_layout_xmlid="mail.mail_notification_paynow")
+
+    def _cron_send_invoice(self):
+        """
+            Cron to send invoice that where not ready to be send directly after posting
+        """
+        if not self.env['ir.config_parameter'].sudo().get_param('sale.automatic_invoice'):
+            return
+
+        # No need to retrieve old transactions
+        retry_limit_date = datetime.now() - relativedelta.relativedelta(days=2)
+        # Retrieve all transactions matching the criteria for post-processing
+        self.search([
+            ('state', '=', 'done'),
+            ('is_post_processed', '=', True),
+            ('invoice_ids', 'in', self.env['account.move']._search([
+                ('is_move_sent', '=', False),
+                ('state', '=', 'posted'),
+            ])),
+            ('sale_order_ids.state', 'in', ('sale', 'done')),
+            ('last_state_change', '>=', retry_limit_date),
+        ])._send_invoice()
+
     def _invoice_sale_orders(self):
         if self.env['ir.config_parameter'].sudo().get_param('sale.automatic_invoice'):
             for trans in self.filtered(lambda t: t.sale_order_ids):
diff --git a/addons/sale/models/res_config_settings.py b/addons/sale/models/res_config_settings.py
index df4482fe99a..242c97d508e 100644
--- a/addons/sale/models/res_config_settings.py
+++ b/addons/sale/models/res_config_settings.py
@@ -75,6 +75,10 @@ class ResConfigSettings(models.TransientModel):
         if self.default_invoice_policy != 'order':
             self.env['ir.config_parameter'].set_param('sale.automatic_invoice', False)
 
+        send_invoice_cron = self.env.ref('sale.send_invoice_cron', raise_if_not_found=False)
+        if send_invoice_cron:
+            send_invoice_cron.active = self.automatic_invoice
+
     @api.onchange('use_quotation_validity_days')
     def _onchange_use_quotation_validity_days(self):
         if self.quotation_validity_days <= 0: