diff --git a/ruby/db/migrate/20250817162004_add_trail_expires_reminder_columns_to_users.rb b/ruby/db/migrate/20250817162004_add_trail_expires_reminder_columns_to_users.rb
new file mode 100644
index 000000000..869fa84a2
--- /dev/null
+++ b/ruby/db/migrate/20250817162004_add_trail_expires_reminder_columns_to_users.rb
@@ -0,0 +1,12 @@
+  class AddTrailExpiresReminderColumnsToUsers < ActiveRecord::Migration
+    def self.up
+       execute "ALTER TABLE users ADD COLUMN trial_expires_reminder1_sent_at TIMESTAMP"
+       execute "ALTER TABLE users ADD COLUMN trial_expires_reminder2_sent_at TIMESTAMP"
+       execute "ALTER TABLE users ADD COLUMN trial_expires_reminder3_sent_at TIMESTAMP"
+    end
+    def self.down
+      execute "ALTER TABLE users DROP COLUMN trial_expires_reminder1_sent_at"
+      execute "ALTER TABLE users DROP COLUMN trial_expires_reminder2_sent_at"
+      execute "ALTER TABLE users DROP COLUMN trial_expires_reminder3_sent_at"
+    end
+  end
diff --git a/ruby/lib/jam_ruby/app/views/jam_ruby/user_mailer/trial_expires_reminder1.html.erb b/ruby/lib/jam_ruby/app/views/jam_ruby/user_mailer/trial_expires_reminder1.html.erb
new file mode 100644
index 000000000..b4ad59e1e
--- /dev/null
+++ b/ruby/lib/jam_ruby/app/views/jam_ruby/user_mailer/trial_expires_reminder1.html.erb
@@ -0,0 +1,14 @@
+<p><%=I18n.t('user_mailer.trial_expires_reminder1.greeting') -%> <%= @user.first_name -%> -</p>
+
+<p>
+  <%=I18n.t('user_mailer.trial_expires_reminder1.paragraph1').html_safe -%>
+</p>
+
+<p>
+  <%=I18n.t('user_mailer.trial_expires_reminder1.paragraph2').html_safe -%>
+</p>
+
+<p>
+  <%=I18n.t('user_mailer.trial_expires_reminder1.regards') -%>,<br />
+  <%=I18n.t('user_mailer.trial_expires_reminder1.signature') -%>
+</p>
\ No newline at end of file
diff --git a/ruby/lib/jam_ruby/app/views/jam_ruby/user_mailer/trial_expires_reminder1.text.erb b/ruby/lib/jam_ruby/app/views/jam_ruby/user_mailer/trial_expires_reminder1.text.erb
new file mode 100644
index 000000000..36c478dfb
--- /dev/null
+++ b/ruby/lib/jam_ruby/app/views/jam_ruby/user_mailer/trial_expires_reminder1.text.erb
@@ -0,0 +1,8 @@
+<%=I18n.t('user_mailer.trial_expires_reminder1.greeting') -%> <%= @user.first_name -%> -
+
+<%=I18n.t('user_mailer.trial_expires_reminder1.paragraph1') -%>
+
+<%=I18n.t('user_mailer.trial_expires_reminder1.paragraph2') -%>
+
+<%=I18n.t('user_mailer.trial_expires_reminder1.regards') -%>,
+<%=I18n.t('user_mailer.trial_expires_reminder1.signature') -%>
\ No newline at end of file
diff --git a/ruby/lib/jam_ruby/app/views/jam_ruby/user_mailer/trial_expires_reminder2.html.erb b/ruby/lib/jam_ruby/app/views/jam_ruby/user_mailer/trial_expires_reminder2.html.erb
new file mode 100644
index 000000000..88f61b0aa
--- /dev/null
+++ b/ruby/lib/jam_ruby/app/views/jam_ruby/user_mailer/trial_expires_reminder2.html.erb
@@ -0,0 +1,18 @@
+<p><%=I18n.t('user_mailer.trial_expires_reminder2.greeting') -%> <%= @user.first_name -%> -</p>
+
+<p>
+  <%=I18n.t('user_mailer.trial_expires_reminder2.paragraph1').html_safe -%>
+</p>
+
+<p>
+  <%=I18n.t('user_mailer.trial_expires_reminder2.paragraph2').html_safe -%>
+</p>
+
+<p>
+  <%=I18n.t('user_mailer.trial_expires_reminder2.paragraph3').html_safe -%>
+</p>
+
+<p>
+  <%=I18n.t('user_mailer.trial_expires_reminder2.regards') -%>,<br />
+  <%=I18n.t('user_mailer.trial_expires_reminder2.signature') -%>
+</p>
\ No newline at end of file
diff --git a/ruby/lib/jam_ruby/app/views/jam_ruby/user_mailer/trial_expires_reminder2.text.erb b/ruby/lib/jam_ruby/app/views/jam_ruby/user_mailer/trial_expires_reminder2.text.erb
new file mode 100644
index 000000000..85d7112b2
--- /dev/null
+++ b/ruby/lib/jam_ruby/app/views/jam_ruby/user_mailer/trial_expires_reminder2.text.erb
@@ -0,0 +1,10 @@
+<%=I18n.t('user_mailer.trial_expires_reminder2.greeting') -%> <%= @user.first_name -%> -
+
+<%=I18n.t('user_mailer.trial_expires_reminder2.paragraph1') -%>
+
+<%=I18n.t('user_mailer.trial_expires_reminder2.paragraph2') -%>
+
+<%=I18n.t('user_mailer.trial_expires_reminder2.paragraph3') -%>
+
+<%=I18n.t('user_mailer.trial_expires_reminder2.regards') -%>,
+<%=I18n.t('user_mailer.trial_expires_reminder2.signature') -%>
\ No newline at end of file
diff --git a/ruby/lib/jam_ruby/app/views/jam_ruby/user_mailer/trial_expires_reminder3.html.erb b/ruby/lib/jam_ruby/app/views/jam_ruby/user_mailer/trial_expires_reminder3.html.erb
new file mode 100644
index 000000000..b5d7f9cc3
--- /dev/null
+++ b/ruby/lib/jam_ruby/app/views/jam_ruby/user_mailer/trial_expires_reminder3.html.erb
@@ -0,0 +1,18 @@
+<p><%=I18n.t('user_mailer.trial_expires_reminder3.greeting') -%> <%= @user.first_name -%> -</p>
+
+<p>
+  <%=I18n.t('user_mailer.trial_expires_reminder3.paragraph1').html_safe -%>
+</p>
+
+<p>
+  <%=I18n.t('user_mailer.trial_expires_reminder3.paragraph2').html_safe -%>
+</p>
+
+<p>
+  <%=I18n.t('user_mailer.trial_expires_reminder3.paragraph3').html_safe -%>
+</p>
+
+<p>
+  <%=I18n.t('user_mailer.trial_expires_reminder3.regards') -%>,<br />
+  <%=I18n.t('user_mailer.trial_expires_reminder3.signature') -%>
+</p>
\ No newline at end of file
diff --git a/ruby/lib/jam_ruby/app/views/jam_ruby/user_mailer/trial_expires_reminder3.text.erb b/ruby/lib/jam_ruby/app/views/jam_ruby/user_mailer/trial_expires_reminder3.text.erb
new file mode 100644
index 000000000..2461bb066
--- /dev/null
+++ b/ruby/lib/jam_ruby/app/views/jam_ruby/user_mailer/trial_expires_reminder3.text.erb
@@ -0,0 +1,10 @@
+<%=I18n.t('user_mailer.trial_expires_reminder3.greeting') -%> <%= @user.first_name -%> -
+
+<%=I18n.t('user_mailer.trial_expires_reminder3.paragraph1') -%>
+
+<%=I18n.t('user_mailer.trial_expires_reminder3.paragraph2') -%>
+
+<%=I18n.t('user_mailer.trial_expires_reminder3.paragraph3') -%>
+
+<%=I18n.t('user_mailer.trial_expires_reminder3.regards') -%>,
+<%=I18n.t('user_mailer.trial_expires_reminder3.signature') -%>
\ No newline at end of file
diff --git a/ruby/lib/jam_ruby/lib/trial_expires_reminder.rb b/ruby/lib/jam_ruby/lib/trial_expires_reminder.rb
new file mode 100644
index 000000000..e4dd9540e
--- /dev/null
+++ b/ruby/lib/jam_ruby/lib/trial_expires_reminder.rb
@@ -0,0 +1,64 @@
+# lib/jam_ruby/lib/trial_expires_reminder.rb
+#
+# Sends reminder emails after a user's free trial has ended.
+#
+# Usage: JamRuby::TrialExpiresReminder.send_reminders
+#
+module JamRuby
+  class TrialExpiresReminder
+    @@log = Logging.logger[TrialExpiresReminder]
+
+    FIRST_NOTIFICATION_CHECK = 1.day.ago.to_s
+    SECOND_NOTIFICATION_CHECK = 5.days.ago.to_s
+    THIRD_NOTIFICATION_CHECK = 9.days.ago
+
+    def self.prospect_users(cutoff_date)
+      User.where("(users.subscription_trial_ends_at IS NOT NULL AND users.subscription_trial_ends_at > ?)", cutoff_date)
+    end
+
+    def self.reminder1_users(cutoff_date)
+      prospect_users(cutoff_date).where("users.subscription_last_checked_at < ? AND users.subscription_trial_ends_at < ? AND users.trial_expires_reminder1_sent_at IS NULL", 1.day.ago, FIRST_NOTIFICATION_CHECK)
+    end
+
+    def self.reminder2_users(cutoff_date)
+      prospect_users(cutoff_date).where("users.subscription_last_checked_at < ? AND users.subscription_trial_ends_at < ? AND trial_expires_reminder1_sent_at IS NOT NULL AND users.trial_expires_reminder2_sent_at IS NULL", 1.day.ago, SECOND_NOTIFICATION_CHECK)
+    end
+
+    def self.reminder3_users(cutoff_date)
+      prospect_users(cutoff_date).where("users.subscription_last_checked_at < ? AND users.subscription_trial_ends_at < ? AND trial_expires_reminder2_sent_at IS NOT NULL AND users.trial_expires_reminder3_sent_at IS NULL", 1.day.ago, THIRD_NOTIFICATION_CHECK)
+    end
+
+    def self.send_reminders
+        cod = Date.parse(Rails.application.config.trial_expires_reminders_effective_from_date) # Define a cutoff date for the trial expires reminder emails
+
+        reminder1_users(cod).find_each(batch_size: 100) do |user|
+          begin
+            UserMailer.trial_expires_reminder1(user).deliver_now
+            user.update_attribute(:trial_expires_reminder1_sent_at, Time.now)
+          rescue Exception => e
+            @@log.error("unable to send trial_expires_reminder1 email #{e}")
+            puts "unable to send trial_expires_reminder1 email #{e}"
+          end
+        end
+        reminder2_users(cod).find_each(batch_size: 100) do |user|
+          begin
+            UserMailer.trial_expires_reminder2(user).deliver_now
+            user.update_attribute(:trial_expires_reminder2_sent_at, Time.now)
+          rescue Exception => e
+            @@log.error("unable to send trial_expires_reminder2 email #{e}")
+            puts "unable to send trial_expires_reminder2 email #{e}"
+          end
+        end
+        reminder3_users(cod).find_each(batch_size: 100) do |user|
+          begin
+            UserMailer.trial_expires_reminder3(user).deliver_now
+            user.update_attribute(:trial_expires_reminder3_sent_at, Time.now)
+          rescue Exception => e
+            @@log.error("unable to send trial_expires_reminder3 email #{e}")
+            puts "unable to send trial_expires_reminder3 email #{e}"
+          end
+        end
+    end
+    
+  end
+end
\ No newline at end of file
diff --git a/ruby/spec/jam_ruby/lib/trail_expires_reminder_spec.rb b/ruby/spec/jam_ruby/lib/trail_expires_reminder_spec.rb
new file mode 100644
index 000000000..9943e6368
--- /dev/null
+++ b/ruby/spec/jam_ruby/lib/trail_expires_reminder_spec.rb
@@ -0,0 +1,116 @@
+require "spec_helper"
+
+describe TrialExpiresReminder do
+  let(:user1) { FactoryGirl.create(:user) }
+  let(:user2) { FactoryGirl.create(:user) }
+  let(:user3) { FactoryGirl.create(:user) }
+
+  before(:each) do
+    ActionMailer::Base.delivery_method = :test
+    ActionMailer::Base.perform_deliveries = true
+    ActionMailer::Base.deliveries = []
+
+    User.delete_all
+    UserMailer.deliveries.clear
+    Rails.application.config.trial_expires_reminders_effective_from_date = 2.weeks.ago.to_s
+  end
+
+  after(:each) do
+    ActionMailer::Base.deliveries.clear
+  end
+
+  it "sends reminder emails to users whose trials are about to expire" do
+    user1.subscription_trial_ends_at = 1.days.from_now
+    user1.subscription_last_checked_at = 2.days.ago
+    user1.save!
+
+    user2.subscription_trial_ends_at = 1.days.ago
+    user2.subscription_last_checked_at = 2.days.ago
+    user2.save!
+
+    TrialExpiresReminder.send_reminders
+    
+    expect(ActionMailer::Base.deliveries.count).to eq(1)
+    expect(ActionMailer::Base.deliveries.map(&:to).flatten).to include(user2.email)
+    # Check if the first reminder email was sent by verifying the subject
+    expect(ActionMailer::Base.deliveries.last.subject).to include("Your free gold trial has expired, but you have great options to keep playing!")
+
+    expect(user2.reload.trial_expires_reminder1_sent_at).not_to be_nil
+  end
+
+  it "does not send reminder emails to users who have already received them" do
+    user1.subscription_trial_ends_at = 1.days.ago
+    user1.subscription_last_checked_at = 2.days.ago
+    user1.trial_expires_reminder1_sent_at = Time.now
+    user1.save!
+
+    TrialExpiresReminder.send_reminders
+
+    expect(ActionMailer::Base.deliveries.count).to eq(0)
+  end
+
+  it "sends the second reminder email to users whose trials are about to expire" do
+    user1.subscription_trial_ends_at = 4.days.ago
+    user1.subscription_last_checked_at = 1.days.ago
+    user1.trial_expires_reminder1_sent_at = Time.now
+    user1.save!
+
+    user2.subscription_trial_ends_at = 5.days.ago
+    user2.subscription_last_checked_at = 1.days.ago
+    user2.trial_expires_reminder1_sent_at = Time.now
+    user2.save!
+
+    TrialExpiresReminder.send_reminders
+                                                                                                                                                                                                               
+    expect(ActionMailer::Base.deliveries.count).to eq(1)
+    expect(ActionMailer::Base.deliveries.map(&:to).flatten).to include(user2.email)
+    # Check if the second reminder email was sent by verifying the subject
+    expect(ActionMailer::Base.deliveries.last.subject).to include("Don’t forget to check your options to keep playing")
+
+    expect(user2.reload.trial_expires_reminder2_sent_at).not_to be_nil
+  end
+
+  it "sends the third reminder email to users whose trials are about to expire" do
+    user1.subscription_trial_ends_at = 10.days.ago
+    user1.subscription_last_checked_at = 1.days.ago
+    user1.trial_expires_reminder1_sent_at = 6.days.ago
+    user1.trial_expires_reminder2_sent_at = 4.days.ago
+    user1.save!
+
+    TrialExpiresReminder.send_reminders
+
+    expect(ActionMailer::Base.deliveries.count).to eq(1)
+    expect(ActionMailer::Base.deliveries.map(&:to).flatten).to include(user1.email)
+    # Check if the third reminder email was sent by verifying the subject
+    expect(ActionMailer::Base.deliveries.last.subject).to include("One last reminder!")
+
+    expect(user1.reload.trial_expires_reminder3_sent_at).not_to be_nil
+  end
+
+  it "sends first and second and third reminder emails to users whose trials are about to expire" do
+    user1.subscription_trial_ends_at = 2.days.ago
+    user1.subscription_last_checked_at = 1.days.ago
+    user1.save!
+
+    user2.subscription_trial_ends_at = 6.days.ago
+    user2.subscription_last_checked_at = 1.days.ago
+    user2.trial_expires_reminder1_sent_at = 4.days.ago
+    user2.save!
+
+    user3.subscription_trial_ends_at = 10.days.ago
+    user3.subscription_last_checked_at = 2.days.ago
+    user3.trial_expires_reminder1_sent_at = 6.days.ago
+    user3.trial_expires_reminder2_sent_at = 4.days.ago
+    user3.save!
+
+    TrialExpiresReminder.send_reminders
+
+    expect(user1.reload.trial_expires_reminder1_sent_at).not_to be_nil
+    expect(user2.reload.trial_expires_reminder2_sent_at).not_to be_nil
+    expect(user3.reload.trial_expires_reminder3_sent_at).not_to be_nil
+
+    expect(ActionMailer::Base.deliveries.count).to eq(3)
+    expect(ActionMailer::Base.deliveries.map(&:to).flatten).to include(user1.email, user2.email, user3.email)
+
+  end
+end
\ No newline at end of file