diff --git a/addons/hr/wizard/hr_departure_wizard.py b/addons/hr/wizard/hr_departure_wizard.py
index 545b444e456..c2284f82aa2 100644
--- a/addons/hr/wizard/hr_departure_wizard.py
+++ b/addons/hr/wizard/hr_departure_wizard.py
@@ -1,16 +1,22 @@
 # -*- coding: utf-8 -*-
 # Part of Odoo. See LICENSE file for full copyright and licensing details.
 
-from odoo import api, fields, models
+from odoo import fields, models
 
 
 class HrDepartureWizard(models.TransientModel):
     _name = 'hr.departure.wizard'
     _description = 'Departure Wizard'
 
+    def _get_default_departure_date(self):
+        departure_date = False
+        if self.env.context.get('active_id'):
+            departure_date = self.env['hr.employee'].browse(self.env.context['active_id']).departure_date
+        return departure_date or fields.Date.today()
+
     departure_reason_id = fields.Many2one("hr.departure.reason", default=lambda self: self.env['hr.departure.reason'].search([], limit=1), required=True)
     departure_description = fields.Html(string="Additional Information")
-    departure_date = fields.Date(string="Departure Date", required=True, default=fields.Date.today)
+    departure_date = fields.Date(string="Departure Date", required=True, default=_get_default_departure_date)
     employee_id = fields.Many2one(
         'hr.employee', string='Employee', required=True,
         default=lambda self: self.env.context.get('active_id', None),
diff --git a/addons/hr_holidays/models/hr_leave.py b/addons/hr_holidays/models/hr_leave.py
index d7a0c66cd60..1d38a5057bf 100644
--- a/addons/hr_holidays/models/hr_leave.py
+++ b/addons/hr_holidays/models/hr_leave.py
@@ -719,7 +719,7 @@ class HolidaysRequest(models.Model):
             leave_days = mapped_days[holiday.employee_id.id][holiday.holiday_status_id.id]
             if float_compare(leave_days['remaining_leaves'], 0, precision_digits=2) == -1 or float_compare(leave_days['virtual_remaining_leaves'], 0, precision_digits=2) == -1:
                 raise ValidationError(_('The number of remaining time off is not sufficient for this time off type.\n'
-                                        'Please also check the time off waiting for validation.'))
+                                        'Please also check the time off waiting for validation.') + '\n- %s' % holiday.display_name)
 
     @api.constrains('date_from', 'date_to', 'employee_id')
     def _check_date_state(self):
@@ -859,7 +859,7 @@ class HolidaysRequest(models.Model):
                 raise ValidationError(_(
                     'Could not find an allocation of type %(leave_type)s for the requested time period.',
                     leave_type=leave.holiday_status_id.display_name,
-                ))
+                ) + '\n- %s' % (leave.employee_id.name))
 
     @api.constrains('holiday_allocation_id', 'date_to', 'date_from')
     def _check_leave_type_validity(self):
diff --git a/addons/hr_work_entry_contract/models/hr_contract.py b/addons/hr_work_entry_contract/models/hr_contract.py
index 769ff1a59bc..7b3bc599811 100644
--- a/addons/hr_work_entry_contract/models/hr_contract.py
+++ b/addons/hr_work_entry_contract/models/hr_contract.py
@@ -5,9 +5,10 @@ from collections import defaultdict
 from datetime import datetime, date
 from dateutil.relativedelta import relativedelta
 
-from odoo import api, fields, models
+from odoo import api, fields, models, _
 from odoo.addons.resource.models.resource import datetime_to_string, string_to_datetime, Intervals
 from odoo.osv import expression
+from odoo.exceptions import UserError
 
 import pytz
 
@@ -178,6 +179,11 @@ class HrContract(models.Model):
         return contract_vals
 
     def _generate_work_entries(self, date_start, date_stop, force=False):
+        canceled_contracts = self.filtered(lambda c: c.state == 'cancel')
+        if canceled_contracts:
+            raise UserError(
+                _("Sorry, generating work entries from cancelled contracts is not allowed.") + '\n%s' % (
+                    ', '.join(canceled_contracts.mapped('name'))))
         vals_list = []
         date_start = fields.Datetime.to_datetime(date_start)
         date_stop = datetime.combine(fields.Datetime.to_datetime(date_stop), datetime.max.time())
diff --git a/addons/hr_work_entry_holidays/models/hr_leave.py b/addons/hr_work_entry_holidays/models/hr_leave.py
index 3c4eb0bd9a3..3545c1d62b6 100644
--- a/addons/hr_work_entry_holidays/models/hr_leave.py
+++ b/addons/hr_work_entry_holidays/models/hr_leave.py
@@ -72,7 +72,10 @@ class HrLeave(models.Model):
             nbr_contracts = self.env['hr.contract'].sudo().search_count(domain)
             if nbr_contracts > 1:
                 contracts = self.env['hr.contract'].sudo().search(domain)
-                raise ValidationError(_('A leave cannot be set across multiple contracts.') + '\n' + ', '.join(contracts.mapped('name')))
+                raise ValidationError(
+                    _('A leave cannot be set across multiple contracts.') + '\n%s\n%s' % (
+                        ', '.join(contracts.mapped('name')),
+                        holiday.display_name))
 
     def _cancel_work_entry_conflict(self):
         """