diff --git a/CHANGELOG.md b/CHANGELOG.md
index 7d2360ffd..af25e2044 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,7 @@
 - Add `include_sentry_event` matcher for RSpec [#2424](https://github.com/getsentry/sentry-ruby/pull/2424)
 - Add support for Sentry Cache instrumentation, when using Rails.cache ([#2380](https://github.com/getsentry/sentry-ruby/pull/2380))
 - Add support for Queue Instrumentation for Sidekiq. [#2403](https://github.com/getsentry/sentry-ruby/pull/2403)
+- Reset trace_id and add root transaction for sidekiq-cron [#2446](https://github.com/getsentry/sentry-ruby/pull/2446)
 
     Note: MemoryStore and FileStore require Rails 8.0+
 
diff --git a/sentry-sidekiq/lib/sentry/sidekiq/cron/job.rb b/sentry-sidekiq/lib/sentry/sidekiq/cron/job.rb
index 937fd797c..954e98311 100644
--- a/sentry-sidekiq/lib/sentry/sidekiq/cron/job.rb
+++ b/sentry-sidekiq/lib/sentry/sidekiq/cron/job.rb
@@ -12,6 +12,32 @@ module Sentry
   module Sidekiq
     module Cron
       module Job
+        def self.enqueueing_method
+          ::Sidekiq::Cron::Job.instance_methods.include?(:enque!) ? :enque! : :enqueue!
+        end
+
+        define_method(enqueueing_method) do |*args|
+          # make sure the current thread has a clean hub
+          Sentry.clone_hub_to_current_thread
+
+          Sentry.with_scope do |scope|
+            Sentry.with_session_tracking do
+              begin
+                scope.set_transaction_name("#{name} (#{klass})")
+
+                transaction = start_transaction(scope)
+                scope.set_span(transaction) if transaction
+                super(*args)
+
+                finish_transaction(transaction, 200)
+              rescue
+                finish_transaction(transaction, 500)
+                raise
+              end
+            end
+          end
+        end
+
         def save
           # validation failed, do nothing
           return false unless super
@@ -34,6 +60,22 @@ def save
 
           true
         end
+
+        def start_transaction(scope)
+          Sentry.start_transaction(
+            name: scope.transaction_name,
+            source: scope.transaction_source,
+            op: "queue.sidekiq-cron",
+            origin: "auto.queue.sidekiq.cron"
+          )
+        end
+
+        def finish_transaction(transaction, status_code)
+          return unless transaction
+
+          transaction.set_http_status(status_code)
+          transaction.finish
+        end
       end
     end
   end
diff --git a/sentry-sidekiq/spec/sentry/sidekiq/cron/job_spec.rb b/sentry-sidekiq/spec/sentry/sidekiq/cron/job_spec.rb
index 4e4f65202..85fcaeb99 100644
--- a/sentry-sidekiq/spec/sentry/sidekiq/cron/job_spec.rb
+++ b/sentry-sidekiq/spec/sentry/sidekiq/cron/job_spec.rb
@@ -5,11 +5,24 @@
 return unless defined?(Sidekiq::Cron::Job)
 
 RSpec.describe Sentry::Sidekiq::Cron::Job do
+  let(:processor) do
+    new_processor
+  end
+
+  let(:transport) do
+    Sentry.get_current_client.transport
+  end
+
   before do
-    perform_basic_setup { |c| c.enabled_patches += [:sidekiq_cron] }
+    perform_basic_setup do |c|
+      c.enabled_patches += [:sidekiq_cron]
+      c.traces_sample_rate = 1.0
+    end
   end
 
   before do
+    Sidekiq::Cron::Job.destroy_all!
+    Sidekiq::Queue.all.each(&:clear)
     schedule_file = 'spec/fixtures/sidekiq-cron-schedule.yml'
     schedule = Sidekiq::Cron::Support.load_yaml(ERB.new(IO.read(schedule_file)).result)
     schedule = schedule.merge(symbol_name: { cron: '* * * * *', class: HappyWorkerWithSymbolName })
@@ -79,4 +92,37 @@
   it 'does not patch ReportingWorker because of invalid schedule' do
     expect(ReportingWorker.ancestors).not_to include(Sentry::Cron::MonitorSchedule)
   end
+
+  describe 'sidekiq-cron' do
+    it 'adds job to sidekiq within transaction' do
+      job = Sidekiq::Cron::Job.new(name: 'test', cron: 'not a crontab', class: 'HappyWorkerForCron')
+      job.send(Sentry::Sidekiq::Cron::Job.enqueueing_method)
+
+      expect(::Sidekiq::Queue.new.size).to eq(1)
+      expect(transport.events.count).to eq(1)
+      event = transport.events.last
+      expect(event.spans.count).to eq(1)
+      expect(event.spans[0][:op]).to eq("queue.publish")
+      expect(event.spans[0][:data]['messaging.destination.name']).to eq('default')
+    end
+
+    it 'adds job to sidekiq within transaction' do
+      job = Sidekiq::Cron::Job.new(name: 'test', cron: 'not a crontab', class: 'HappyWorkerForCron')
+      job.send(Sentry::Sidekiq::Cron::Job.enqueueing_method)
+      # Time passes.
+      job.send(Sentry::Sidekiq::Cron::Job.enqueueing_method)
+
+      expect(::Sidekiq::Queue.new.size).to eq(2)
+      expect(transport.events.count).to eq(2)
+      events = transport.events
+      expect(events[0].spans.count).to eq(1)
+      expect(events[0].spans[0][:op]).to eq("queue.publish")
+      expect(events[0].spans[0][:data]['messaging.destination.name']).to eq('default')
+      expect(events[1].spans.count).to eq(1)
+      expect(events[1].spans[0][:op]).to eq("queue.publish")
+      expect(events[1].spans[0][:data]['messaging.destination.name']).to eq('default')
+
+      expect(events[0].dynamic_sampling_context['trace_id']).to_not eq(events[1].dynamic_sampling_context['trace_id'])
+    end
+  end
 end