diff --git a/addons/hr/models/hr_employee.py b/addons/hr/models/hr_employee.py
index 1b0eb784eba984..40a983b4793d01 100644
--- a/addons/hr/models/hr_employee.py
+++ b/addons/hr/models/hr_employee.py
@@ -216,7 +216,6 @@ def _lang_get(self):
     }
     """
 
-    permit_no = fields.Char('Work Permit No', groups="hr.group_hr_user", tracking=True)
     visa_no = fields.Char('Visa No', groups="hr.group_hr_user", tracking=True)
     visa_expire = fields.Date('Visa Expiration Date', groups="hr.group_hr_user", tracking=True)
     work_permit_expiration_date = fields.Date('Work Permit Expiration Date', groups="hr.group_hr_user", tracking=True)
@@ -258,6 +257,8 @@ def _lang_get(self):
         related='version_id.country_id.code',
         groups="hr.group_hr_user"
     )
+    permit_no = fields.Char('Work Permit No', readonly=False, related="version_id.permit_no", inherited=True, groups="hr.group_hr_user", tracking=True)
+
     # Direct subordinates
     parent_id = fields.Many2one('hr.employee', 'Manager', tracking=True, index=True,
                                 domain="['|', ('company_id', '=', False), ('company_id', 'in', allowed_company_ids)]")
diff --git a/addons/hr/models/hr_version.py b/addons/hr/models/hr_version.py
index 1e0a2c9fd0f175..86a6fd7fd54a05 100644
--- a/addons/hr/models/hr_version.py
+++ b/addons/hr/models/hr_version.py
@@ -118,6 +118,7 @@ def _get_hr_responsible_domain(self):
     spouse_complete_name = fields.Char(string="Spouse Legal Name", groups="hr.group_hr_user", tracking=1)
     spouse_birthdate = fields.Date(string="Spouse Birthdate", groups="hr.group_hr_user", tracking=1)
     children = fields.Integer(string='Dependent Children', groups="hr.group_hr_user", tracking=1)
+    permit_no = fields.Char('Work Permit No', groups="hr.group_hr_user", tracking=1)
 
     # Work Information
     department_id = fields.Many2one('hr.department', check_company=True, tracking=1, index=True)
diff --git a/addons/hr/views/hr_employee_views.xml b/addons/hr/views/hr_employee_views.xml
index 74f6252d3774b1..a6b0da8882114c 100644
--- a/addons/hr/views/hr_employee_views.xml
+++ b/addons/hr/views/hr_employee_views.xml
@@ -387,8 +387,8 @@
                                             <field name="contract_date_start" string="Start Date" placeholder="Not Employed" class="o_hr_narrow_field me-3"/>
                                             <span invisible="not contract_date_start">to</span>
                                             <field name="contract_date_end" string="End Date" placeholder="Indefinite" widget="date_dynamic_min" options="{'min_date_field': 'contract_date_start'}"
-                                                class="o_hr_narrow_field ms-3" invisible="not contract_date_start"/>
-                                            <widget name="button_new_contract"/>
+                                                class="o_hr_narrow_field ms-3" invisible="not contract_date_start" required="fixed_term"/>
+                                            <widget name="button_new_contract" invisible="not contract_date_start" />
                                         </div>
                                         <field name="fixed_term" string="Fixed Term" invisible="1"/>
                                         <label for="wage"/>
diff --git a/addons/hr_holidays/models/hr_work_entry_type.py b/addons/hr_holidays/models/hr_work_entry_type.py
index 0473b4b3e9514e..1fe00371990683 100644
--- a/addons/hr_holidays/models/hr_work_entry_type.py
+++ b/addons/hr_holidays/models/hr_work_entry_type.py
@@ -279,7 +279,7 @@ def _search_max_leaves(self, operator, value):
 
     def _search_virtual_remaining_leaves(self, operator, value):
         def is_valid(work_entry_type):
-            return not work_entry_type.requires_allocation or op(work_entry_type.virtual_remaining_leaves)
+            return not work_entry_type.requires_allocation or op(work_entry_type.virtual_remaining_leaves, value)
         op = PY_OPERATORS.get(operator)
         if not op:
             return NotImplemented
diff --git a/addons/hr_holidays/static/src/components/accrual_level/accrual_levels.scss b/addons/hr_holidays/static/src/components/accrual_level/accrual_levels.scss
index f6a930fd221024..93843403dfabfa 100644
--- a/addons/hr_holidays/static/src/components/accrual_level/accrual_levels.scss
+++ b/addons/hr_holidays/static/src/components/accrual_level/accrual_levels.scss
@@ -10,7 +10,7 @@
 }
 
 .o_accrual {
-  .o_field_accrual, .o_field_selection, .o_field_filterable_selection {
+  .o_field_accrual, .o_field_selection, .o_field_day_selection, .o_field_filterable_selection {
     width: fit-content !important;
 
     &:not(.o_readonly_modifier) > *:first-child {
diff --git a/addons/hr_holidays/static/src/components/day_selection/day_selection.js b/addons/hr_holidays/static/src/components/day_selection/day_selection.js
new file mode 100644
index 00000000000000..2f459c64e2d145
--- /dev/null
+++ b/addons/hr_holidays/static/src/components/day_selection/day_selection.js
@@ -0,0 +1,34 @@
+import { registry } from "@web/core/registry";
+import { SelectionField, selectionField } from "@web/views/fields/selection/selection_field";
+
+export class DaySelection extends SelectionField {
+    static props = {
+        ...SelectionField.props,
+        month: { type: String, optional: true },
+    };
+
+    get options() {
+        const options = super.options;
+        const selectedMonth = this.props.record.data[this.props.month];
+        if (!selectedMonth) return options;
+
+        const maxDays = new Date(2024, parseInt(selectedMonth), 0).getDate();
+        return options.filter(option => parseInt(option[0]) <= maxDays);
+    }
+}
+
+export const daySelection = {
+    ...selectionField,
+    component: DaySelection,
+    extractProps({ attrs }) {
+        const props = selectionField.extractProps(...arguments);
+        props.month = attrs.month;
+        return props;
+    },
+    fieldDependencies: ({ attrs }) => [
+        { name: attrs.month, type: "selection" },
+    ],
+};
+
+
+registry.category("fields").add("day_selection", daySelection);
diff --git a/addons/hr_holidays/tests/__init__.py b/addons/hr_holidays/tests/__init__.py
index 2131051075109c..f17a7354a68cb4 100644
--- a/addons/hr_holidays/tests/__init__.py
+++ b/addons/hr_holidays/tests/__init__.py
@@ -38,3 +38,4 @@
 from . import test_timeoff_overview_my_department_tour
 from . import test_hr_leave_report
 from . import test_member_of_department
+from . import test_time_off_type
diff --git a/addons/hr_holidays/tests/test_time_off_type.py b/addons/hr_holidays/tests/test_time_off_type.py
new file mode 100644
index 00000000000000..d5aa057bcc4610
--- /dev/null
+++ b/addons/hr_holidays/tests/test_time_off_type.py
@@ -0,0 +1,34 @@
+from odoo.addons.hr_holidays.tests.common import TestHrHolidaysCommon
+
+
+class TestTimeOffType(TestHrHolidaysCommon):
+
+    @classmethod
+    def setUpClass(cls):
+
+        super().setUpClass()
+
+        cls.work_entry_type_paid = cls.env['hr.work.entry.type'].create({
+            'name': 'Paid Time Off',
+            'code': 'Paid Time Off',
+            'requires_allocation': True,
+            'request_unit': 'day',
+            'unit_of_measure': 'day',
+            'allows_negative': False,
+        })
+
+        cls.allocation = cls.env['hr.leave.allocation'].create({
+                'name': 'Regular allocation',
+                'date_from': '2024-01-04',
+                'work_entry_type_id': cls.work_entry_type_paid.id,
+                'employee_id': cls.employee_emp.id,
+                'number_of_days': 10,
+        })
+        cls.allocation.action_approve()
+
+    def test_time_off_type_selection_with_existing_allocations(self):
+        self.env['hr.work.entry.type'].with_context(
+                default_employee_id=self.employee_emp.id,
+        ).search([
+            ('virtual_remaining_leaves', '>', 0),
+        ])
diff --git a/addons/hr_holidays/views/hr_leave_accrual_views.xml b/addons/hr_holidays/views/hr_leave_accrual_views.xml
index 0630b086ad787e..12fe7b3836927c 100644
--- a/addons/hr_holidays/views/hr_leave_accrual_views.xml
+++ b/addons/hr_holidays/views/hr_leave_accrual_views.xml
@@ -36,17 +36,17 @@
                                 </span>
                                 <span name="biyearly" invisible="frequency != 'biyearly'">
                                     on the
-                                    <field nolabel="1" name="first_month_day" class="o_hr_narrow_field-3" placeholder="select a day" required="frequency == 'biyearly'"/>
+                                    <field nolabel="1" name="first_month_day" widget="day_selection" month="first_month" class="o_hr_narrow_field-3" placeholder="select a day" required="frequency == 'biyearly'"/>
                                     of
                                     <field name="first_month" class="o_hr_narrow_field-5" placeholder="select a month" required="frequency == 'biyearly'"/>
                                     and the
-                                    <field nolabel="1" name="second_month_day" class="o_hr_narrow_field-3" placeholder="select a day" required="frequency == 'biyearly'"/>
+                                    <field nolabel="1" name="second_month_day" widget="day_selection" month="second_month" class="o_hr_narrow_field-3" placeholder="select a day" required="frequency == 'biyearly'"/>
                                     of
                                     <field nolabel="1" name="second_month" class="o_hr_narrow_field-5" placeholder="select a month" required="frequency == 'biyearly'"/>
                                 </span>
                                 <span name="yearly" invisible="frequency != 'yearly'">
                                     on the
-                                    <field nolabel="1" name="yearly_day" class="o_hr_narrow_field-3" required="frequency == 'yearly'" placeholder="select a day"/>
+                                    <field nolabel="1" name="yearly_day" widget="day_selection" month="yearly_month" class="o_hr_narrow_field-3" required="frequency == 'yearly'" placeholder="select a day"/>
                                     of
                                     <field nolabel="1" name="yearly_month" class="o_hr_narrow_field-5" required="frequency == 'yearly'" placeholder="select a month"/>
                                 </span>
@@ -204,8 +204,8 @@
                                                options="{'links': {'other': 'carryover_custom_date'}, 'observe': 'carryover'}"/>
                                         <span id="carryover_custom_date">
                                             : the
-                                            <field name="carryover_day" placeholder="select a day"
-                                                   required="carryover_date == 'other'"/>
+                                            <field name="carryover_day" placeholder="select a day" widget="day_selection" month="carryover_month"
+                                                   required="carryover_date == 'other'" class="w-100"/>
                                             of
                                             <field name="carryover_month" placeholder="select a month"
                                                    required="carryover_date == 'other'"/>