diff --git a/app/assets/javascripts/application.js.coffee b/app/assets/javascripts/application.js.coffee
index 269700e83..7eaf4db51 100644
--- a/app/assets/javascripts/application.js.coffee
+++ b/app/assets/javascripts/application.js.coffee
@@ -49,6 +49,7 @@
 #= require invoices
 #= require cockpit
 #= require turbolinks
+#= require employments
 
 app = window.App ||= {}
 
diff --git a/app/assets/javascripts/employments.js.coffee b/app/assets/javascripts/employments.js.coffee
new file mode 100644
index 000000000..0ac655871
--- /dev/null
+++ b/app/assets/javascripts/employments.js.coffee
@@ -0,0 +1,18 @@
+#  Copyright (c) 2006-2017, Puzzle ITC GmbH. This file is part of
+#  PuzzleTime and licensed under the Affero General Public License version 3
+#  or later. See the COPYING file at the top-level directory or at
+#  https://github.com/puzzle/puzzletime.
+
+$ ->
+  form = $('form[data-needs-confirmation="true"]')
+  return unless form.length
+  return if form.data('confirmed')
+
+  if confirm('Möglicherweise ging vergessen die Ferientage pro Jahr einzutragen. Dennoch fortfahren?')
+    $('<input>')
+      .attr('type', 'hidden')
+      .attr('name', 'confirmed')
+      .val('true')
+      .appendTo(form)
+    form.data('confirmed', true)
+    form.submit()
diff --git a/app/controllers/employments_controller.rb b/app/controllers/employments_controller.rb
index 6762e81ad..fd34feef5 100644
--- a/app/controllers/employments_controller.rb
+++ b/app/controllers/employments_controller.rb
@@ -24,6 +24,7 @@ class EmploymentsController < ManageController
   before_render_form :load_employment_role_levels
   before_render_form :prefill_from_newest_employment
 
+  before_save :check_vacation_days_set
   before_save :check_percent
   before_save :check_employment_role_uniqueness
 
@@ -52,6 +53,13 @@ def prefill_from_newest_employment
     entry.employment_roles_employments = newest.employment_roles_employments.map(&:dup)
   end
 
+  def check_vacation_days_set
+    return unless entry.needs_vacation_days_confirmation? && !params[:confirmed]
+
+    @needs_confirmation = true
+    throw :abort
+  end
+
   def check_percent
     employment_roles_employments =
       params[:employment][:employment_roles_employments_attributes] || {}
diff --git a/app/models/employment.rb b/app/models/employment.rb
index d25fbfdaa..3f4d3dec8 100644
--- a/app/models/employment.rb
+++ b/app/models/employment.rb
@@ -128,6 +128,17 @@ def date_label(date)
     date ? I18n.l(date) : 'offen'
   end
 
+  # Defines if confirmation before save is needed when vacation days are left empty
+  # Applies when latest employment is not older than one year and had vacation days set
+  def needs_vacation_days_confirmation?
+    latest = Employment.where(employee_id: employee_id)
+                       .order(start_date: :desc).first
+    return false unless latest
+    return false if latest.end_date && latest.end_date < 1.year.ago.to_date
+
+    latest.vacation_days_per_year.present? && vacation_days_per_year.blank?
+  end
+
   private
 
   def vacations_per_period(period, days_per_year)
diff --git a/app/views/employments/_form.html.haml b/app/views/employments/_form.html.haml
index 395819cf0..39ec7ea2a 100644
--- a/app/views/employments/_form.html.haml
+++ b/app/views/employments/_form.html.haml
@@ -6,7 +6,7 @@
 
 - @title = ti(:title, model: "#{models_label(false)} von #{h(parent)}")
 
-= crud_form do |f|
+= crud_form data: { needs_confirmation: @needs_confirmation } do |f|
   = f.labeled_input_fields :start_date, :end_date
   = f.labeled_input_field :percent, min: 0, max: 200, step: 2.5
   = f.labeled_input_field :vacation_days_per_year, help: 'Feld leer lassen, um den Wert aus den allgemeinen Anstellungsbedingungen zu verwenden.'
diff --git a/test/integration/create_employment_test.rb b/test/integration/create_employment_test.rb
new file mode 100644
index 000000000..b20b81fd7
--- /dev/null
+++ b/test/integration/create_employment_test.rb
@@ -0,0 +1,44 @@
+# frozen_string_literal: true
+
+#  Copyright (c) 2006-2025, Puzzle ITC GmbH. This file is part of
+#  PuzzleTime and licensed under the Affero General Public License version 3
+#  or later. See the COPYING file at the top-level directory or at
+#  https://github.com/puzzle/puzzletime.
+
+require 'test_helper'
+
+class CreateEmploymentTest < ActionDispatch::IntegrationTest
+  setup :init_view
+
+  test 'new employment' do
+    page.assert_selector('tbody tr', count: 1)
+    click_link 'Erstellen'
+
+    page.assert_selector('h1', text: "Anstellung von #{employee.lastname} #{employee.firstname} erstellen")
+
+    fill_in 'employment_start_date', with: Date.current
+    fill_in 'employment_end_date', with: Date.current + 1
+    accept_confirm('Möglicherweise ging vergessen die Ferientage pro Jahr einzutragen. Dennoch fortfahren?') do
+      click_button 'Speichern'
+    end
+
+    assert_current_path(
+      "#{employee_employments_path(employee)}?returning=true",
+      ignore_query: false
+    )
+
+    page.assert_selector('tbody tr', count: 2)
+  end
+
+  private
+
+  def employee
+    @employee ||= Fabricate(:employee, management: true)
+  end
+
+  def init_view
+    _employment = Fabricate(:employment, employee:, start_date: 2.years.ago.to_date, end_date: 1.day.ago.to_date, percent: 80, vacation_days_per_year: 27)
+    login_as employee
+    visit employee_employments_path(employee)
+  end
+end
diff --git a/test/models/employment_test.rb b/test/models/employment_test.rb
index 737359370..6ae88c743 100644
--- a/test/models/employment_test.rb
+++ b/test/models/employment_test.rb
@@ -117,6 +117,33 @@ def test_before_create_updates_previous_end_date
     assert_equal Date.parse('1.6.2013'), before2.end_date
   end
 
+  def test_confirmation_vacation_days_set
+    employee = Fabricate(:employee)
+    # Last employment has custom vacation days set
+    _old = Fabricate(:employment, employee:, start_date: 2.years.ago.to_date, end_date: nil, percent: 80, vacation_days_per_year: 27)
+    new = Employment.new(employee:, start_date: 1.day.ago.to_date, end_date: nil, percent: 80, vacation_days_per_year: nil)
+
+    assert_predicate new, :needs_vacation_days_confirmation?
+  end
+
+  def test_confirmation_vacation_days_not_set
+    employee = Fabricate(:employee)
+    # Last employment has no custom vacation days set
+    _old = Fabricate(:employment, employee:, start_date: 2.years.ago.to_date, end_date: nil, percent: 80, vacation_days_per_year: nil)
+    new = Employment.new(employee:, start_date: 1.day.ago.to_date, end_date: nil, percent: 80, vacation_days_per_year: nil)
+
+    assert_not_predicate new, :needs_vacation_days_confirmation?
+  end
+
+  def test_confirmation_latest_employement_long_ago
+    employee = Fabricate(:employee)
+    # Last employment has ended two years ago
+    _old = Fabricate(:employment, employee:, start_date: 5.years.ago.to_date, end_date: 2.years.ago.to_date, percent: 80, vacation_days_per_year: 27)
+    new = Employment.new(employee:, start_date: 1.day.ago.to_date, end_date: nil, percent: 80, vacation_days_per_year: nil)
+
+    assert_not_predicate new, :needs_vacation_days_confirmation?
+  end
+
   def test_vactions
     assert_equal 20, new_employment('1.1.2000', '31.12.2000').vacations
     assert_equal 40, new_employment('1.1.2000', '31.12.2001').vacations