diff --git a/.github/workflows/build_batch_release.yml b/.github/workflows/build_batch_release.yml
index ffc30fcbd..ff584e14d 100644
--- a/.github/workflows/build_batch_release.yml
+++ b/.github/workflows/build_batch_release.yml
@@ -17,7 +17,7 @@ jobs:
     - name: Build gem source
       run:  ruby .scripts/batch_build.rb
     - name: Archive Artifacts
-      uses: actions/upload-artifact@v3.1.1
+      uses: actions/upload-artifact@v4
       with:
         name: ${{ github.sha }}
         path: sentry*/*.gem
diff --git a/.github/workflows/build_release.yml b/.github/workflows/build_release.yml
index f9cad4c6e..3dfe24f81 100644
--- a/.github/workflows/build_release.yml
+++ b/.github/workflows/build_release.yml
@@ -27,7 +27,7 @@ jobs:
       working-directory: ${{env.sdk-directory}}
       run: make build
     - name: Archive Artifacts
-      uses: actions/upload-artifact@v3.1.1
+      uses: actions/upload-artifact@v4
       with:
         name: ${{ github.sha }}
         path: ${{env.sdk-directory}}/*.gem
diff --git a/.github/workflows/sentry_ruby_test.yml b/.github/workflows/sentry_ruby_test.yml
index a154df326..688b54042 100644
--- a/.github/workflows/sentry_ruby_test.yml
+++ b/.github/workflows/sentry_ruby_test.yml
@@ -29,7 +29,7 @@ jobs:
       fail-fast: false
       matrix:
         ruby_version: ${{ fromJson(needs.ruby-versions.outputs.versions) }}
-        rack_version: [2.0, 3.0]
+        rack_version: [2.0, 3.0, 3.1]
         redis_rb_version: [4.0]
         include:
           - { ruby_version: 3.2, rack_version: 0, redis_rb_version: 5.0 }
@@ -45,8 +45,12 @@ jobs:
             }
           - {
               ruby_version: 3.2,
-              rack_version: 3.0,
-              redis_rb_version: 5.0,
+              rack_version: 3.0
+            }
+          - {
+              ruby_version: 3.3,
+              rack_version: 3.1,
+              redis_rb_version: 5.3,
               options: { codecov: 1 },
             }
     steps:
@@ -69,6 +73,7 @@ jobs:
           RACK_VERSION: ${{ matrix.rack_version }}
           REDIS_RB_VERSION: ${{ matrix.redis_rb_version }}
         run: |
+          bundle config set without 'rubocop'
           bundle install --jobs 4 --retry 3
           bundle exec rake
 
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 5937ee550..bac1d3102 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,6 +1,9 @@
 ## Unreleased
 
+### Features
+
 - Add support for $SENTRY_DEBUG and $SENTRY_SPOTLIGHT ([#2374](https://github.com/getsentry/sentry-ruby/pull/2374))
+- Support human readable intervals in `sidekiq-cron` ([#2387](https://github.com/getsentry/sentry-ruby/pull/2387))
 - Add support for Sentry Cache instrumentation, when using Rails.cache ([#2380](https://github.com/getsentry/sentry-ruby/pull/2380))
 
 ## 5.19.0
@@ -32,7 +35,7 @@
   ```
 
 - Transaction data are now included in the context ([#2365](https://github.com/getsentry/sentry-ruby/pull/2365))
-  - Closes [#2364](https://github.com/getsentry/sentry-ruby/issues/2363)
+  - Closes [#2363](https://github.com/getsentry/sentry-ruby/issues/2363)
 
 - Inject Sentry meta tags in the Rails application layout automatically in the generator ([#2369](https://github.com/getsentry/sentry-ruby/pull/2369))
 
diff --git a/Gemfile b/Gemfile
index c42bc20c6..c897e543f 100644
--- a/Gemfile
+++ b/Gemfile
@@ -19,5 +19,7 @@ gem "simplecov"
 gem "simplecov-cobertura", "~> 1.4"
 gem "rexml"
 
-gem "rubocop-rails-omakase"
-gem "rubocop-packaging"
+group :rubocop do
+  gem "rubocop-rails-omakase"
+  gem "rubocop-packaging"
+end
diff --git a/sentry-ruby/spec/sentry/event_spec.rb b/sentry-ruby/spec/sentry/event_spec.rb
index 5eeb232f9..ea59f95e1 100644
--- a/sentry-ruby/spec/sentry/event_spec.rb
+++ b/sentry-ruby/spec/sentry/event_spec.rb
@@ -66,7 +66,7 @@
     end
   end
 
-  context 'rack context specified', rack: true do
+  context 'rack context specified', when: :rack_available? do
     require 'stringio'
 
     before do
diff --git a/sentry-ruby/spec/sentry/profiler_spec.rb b/sentry-ruby/spec/sentry/profiler_spec.rb
index 215e739be..e0cba8177 100644
--- a/sentry-ruby/spec/sentry/profiler_spec.rb
+++ b/sentry-ruby/spec/sentry/profiler_spec.rb
@@ -1,8 +1,6 @@
 require "spec_helper"
 
-return unless defined?(StackProf)
-
-RSpec.describe Sentry::Profiler do
+RSpec.describe Sentry::Profiler, when: :stack_prof_installed? do
   before do
     perform_basic_setup do |config|
       config.traces_sample_rate = 1.0
diff --git a/sentry-ruby/spec/sentry/rack/capture_exceptions_spec.rb b/sentry-ruby/spec/sentry/rack/capture_exceptions_spec.rb
index e03984cdf..dfd42ab33 100644
--- a/sentry-ruby/spec/sentry/rack/capture_exceptions_spec.rb
+++ b/sentry-ruby/spec/sentry/rack/capture_exceptions_spec.rb
@@ -1,8 +1,6 @@
 require 'spec_helper'
 
-return unless defined?(Rack)
-
-RSpec.describe Sentry::Rack::CaptureExceptions, rack: true do
+RSpec.describe 'Sentry::Rack::CaptureExceptions', when: :rack_available? do
   let(:exception) { ZeroDivisionError.new("divided by 0") }
   let(:additional_headers) { {} }
   let(:env) { Rack::MockRequest.env_for("/test", additional_headers) }
@@ -14,7 +12,7 @@
 
     it 'captures the exception from direct raise' do
       app = ->(_e) { raise exception }
-      stack = described_class.new(app)
+      stack = Sentry::Rack::CaptureExceptions.new(app)
 
       expect { stack.call(env) }.to raise_error(ZeroDivisionError)
 
@@ -27,7 +25,7 @@
 
     it 'has the correct mechanism' do
       app = ->(_e) { raise exception }
-      stack = described_class.new(app)
+      stack = Sentry::Rack::CaptureExceptions.new(app)
 
       expect { stack.call(env) }.to raise_error(ZeroDivisionError)
 
@@ -41,7 +39,7 @@
         e['rack.exception'] = exception
         [200, {}, ['okay']]
       end
-      stack = described_class.new(app)
+      stack = Sentry::Rack::CaptureExceptions.new(app)
 
       expect do
         stack.call(env)
@@ -57,7 +55,7 @@
         e['sinatra.error'] = exception
         [200, {}, ['okay']]
       end
-      stack = described_class.new(app)
+      stack = Sentry::Rack::CaptureExceptions.new(app)
 
       expect do
         stack.call(env)
@@ -72,7 +70,7 @@
         e['rack.exception'] = exception
         [200, {}, ['okay']]
       end
-      stack = described_class.new(app)
+      stack = Sentry::Rack::CaptureExceptions.new(app)
 
       stack.call(env)
 
@@ -88,7 +86,7 @@
         [200, { 'content-type' => 'text/plain' }, ['OK']]
       end
 
-      stack = described_class.new(Rack::Lint.new(app))
+      stack = Sentry::Rack::CaptureExceptions.new(Rack::Lint.new(app))
       expect { stack.call(env) }.to_not raise_error
       expect(env.key?("sentry.error_event_id")).to eq(false)
     end
@@ -111,7 +109,7 @@
           a / b
         end
 
-        stack = described_class.new(app)
+        stack = Sentry::Rack::CaptureExceptions.new(app)
 
         expect { stack.call(env) }.to raise_error(ZeroDivisionError)
 
@@ -135,7 +133,7 @@ def inspect
           a / b
         end
 
-        stack = described_class.new(app)
+        stack = Sentry::Rack::CaptureExceptions.new(app)
 
         expect { stack.call(env) }.to raise_error(ZeroDivisionError)
 
@@ -153,7 +151,7 @@ def inspect
           a / b
         end
 
-        stack = described_class.new(app)
+        stack = Sentry::Rack::CaptureExceptions.new(app)
 
         expect { stack.call(env) }.to raise_error(ZeroDivisionError)
 
@@ -181,7 +179,7 @@ def inspect
           [200, {}, ["ok"]]
         end
 
-        app_1 = described_class.new(request_1)
+        app_1 = Sentry::Rack::CaptureExceptions.new(request_1)
 
         app_1.call(env)
 
@@ -195,7 +193,7 @@ def inspect
           Sentry.capture_message("test")
           [200, {}, ["ok"]]
         end
-        app_1 = described_class.new(request_1)
+        app_1 = Sentry::Rack::CaptureExceptions.new(request_1)
 
         app_1.call(env)
 
@@ -209,7 +207,7 @@ def inspect
           e['rack.exception'] = Exception.new
           [200, {}, ["ok"]]
         end
-        app_1 = described_class.new(request_1)
+        app_1 = Sentry::Rack::CaptureExceptions.new(request_1)
         app_1.call(env)
 
         event = last_sentry_event
@@ -221,7 +219,7 @@ def inspect
           e['rack.exception'] = Exception.new
           [200, {}, ["ok"]]
         end
-        app_2 = described_class.new(request_2)
+        app_2 = Sentry::Rack::CaptureExceptions.new(request_2)
         app_2.call(env)
 
         event = last_sentry_event
@@ -250,7 +248,7 @@ def inspect
       end
 
       let(:stack) do
-        described_class.new(
+        Sentry::Rack::CaptureExceptions.new(
           ->(_) do
             [200, {}, ["ok"]]
           end
@@ -438,7 +436,7 @@ def will_be_sampled_by_sdk
           [200, {}, ["ok"]]
         end
 
-        stack = described_class.new(app)
+        stack = Sentry::Rack::CaptureExceptions.new(app)
 
         stack.call(env)
 
@@ -462,7 +460,7 @@ def will_be_sampled_by_sdk
             end
           end
 
-          stack = described_class.new(app)
+          stack = Sentry::Rack::CaptureExceptions.new(app)
 
           stack.call(env)
 
@@ -496,7 +494,7 @@ def will_be_sampled_by_sdk
           [200, {}, ["ok"]]
         end
 
-        stack = described_class.new(app)
+        stack = Sentry::Rack::CaptureExceptions.new(app)
 
         stack.call(env)
 
@@ -514,7 +512,7 @@ def will_be_sampled_by_sdk
           raise "foo"
         end
 
-        stack = described_class.new(app)
+        stack = Sentry::Rack::CaptureExceptions.new(app)
 
         expect do
           stack.call(env)
@@ -541,7 +539,7 @@ def will_be_sampled_by_sdk
       end
 
       let(:stack) do
-        described_class.new(
+        Sentry::Rack::CaptureExceptions.new(
           ->(_) do
             [200, {}, ["ok"]]
           end
@@ -588,7 +586,7 @@ def will_be_sampled_by_sdk
 
     let(:stack) do
       app = ->(_e) { raise exception }
-      described_class.new(app)
+      Sentry::Rack::CaptureExceptions.new(app)
     end
 
     before { perform_basic_setup }
@@ -620,7 +618,7 @@ def will_be_sampled_by_sdk
 
         expect_any_instance_of(Sentry::Hub).not_to receive(:start_session)
         expect(Sentry.session_flusher).to be_nil
-        stack = described_class.new(app)
+        stack = Sentry::Rack::CaptureExceptions.new(app)
         stack.call(env)
 
         expect(sentry_envelopes.count).to eq(0)
@@ -646,7 +644,7 @@ def will_be_sampled_by_sdk
           end
         end
 
-        stack = described_class.new(app)
+        stack = Sentry::Rack::CaptureExceptions.new(app)
 
         expect(Sentry.session_flusher).not_to be_nil
 
@@ -709,7 +707,7 @@ def will_be_sampled_by_sdk
             [200, {}, "ok"]
           end
 
-          stack = described_class.new(app)
+          stack = Sentry::Rack::CaptureExceptions.new(app)
           stack.call(env)
           event = last_sentry_event
 
diff --git a/sentry-ruby/spec/sentry/scope/setters_spec.rb b/sentry-ruby/spec/sentry/scope/setters_spec.rb
index 3ca240488..6a5378194 100644
--- a/sentry-ruby/spec/sentry/scope/setters_spec.rb
+++ b/sentry-ruby/spec/sentry/scope/setters_spec.rb
@@ -7,7 +7,7 @@
     new_breadcrumb
   end
 
-  describe "#set_rack_env", rack: true do
+  describe "#set_rack_env", when: :rack_available? do
     let(:env) do
       Rack::MockRequest.env_for("/test", {})
     end
diff --git a/sentry-ruby/spec/sentry/scope_spec.rb b/sentry-ruby/spec/sentry/scope_spec.rb
index 5de4d8d6d..9b52244a8 100644
--- a/sentry-ruby/spec/sentry/scope_spec.rb
+++ b/sentry-ruby/spec/sentry/scope_spec.rb
@@ -309,7 +309,7 @@
       expect(event.dynamic_sampling_context).to eq(subject.propagation_context.get_dynamic_sampling_context)
     end
 
-    context "with Rack", rack: true do
+    context "with Rack", when: :rack_available? do
       let(:env) do
         Rack::MockRequest.env_for("/test", {})
       end
diff --git a/sentry-ruby/spec/spec_helper.rb b/sentry-ruby/spec/spec_helper.rb
index 611205163..2758a0a1f 100644
--- a/sentry-ruby/spec/spec_helper.rb
+++ b/sentry-ruby/spec/spec_helper.rb
@@ -46,8 +46,10 @@
     ENV.delete('RACK_ENV')
   end
 
-  config.before(:each, rack: true) do
-    skip("skip rack related tests") unless defined?(Rack)
+  config.before(:each, when: true) do |example|
+    meth = example.metadata[:when]
+
+    skip("Skipping because `when: #{meth}` returned false") unless TestHelpers.public_send(meth, example)
   end
 
   RSpec::Matchers.define :have_recorded_lost_event do |reason, data_category, num: 1|
@@ -57,6 +59,16 @@
   end
 end
 
+module TestHelpers
+  def self.stack_prof_installed?(_example)
+    defined?(StackProf)
+  end
+
+  def self.rack_available?(_example)
+    defined?(Rack)
+  end
+end
+
 def fixtures_root
   @fixtures_root ||= Pathname(__dir__).join("fixtures")
 end
diff --git a/sentry-sidekiq/lib/sentry/sidekiq/cron/job.rb b/sentry-sidekiq/lib/sentry/sidekiq/cron/job.rb
index 4098d7564..937fd797c 100644
--- a/sentry-sidekiq/lib/sentry/sidekiq/cron/job.rb
+++ b/sentry-sidekiq/lib/sentry/sidekiq/cron/job.rb
@@ -28,8 +28,8 @@ def save
           unless klass_const.send(:ancestors).include?(Sentry::Cron::MonitorCheckIns)
             klass_const.send(:include, Sentry::Cron::MonitorCheckIns)
             klass_const.send(:sentry_monitor_check_ins,
-                             slug: name,
-                             monitor_config: Sentry::Cron::MonitorConfig.from_crontab(cron))
+                             slug: name.to_s,
+                             monitor_config: Sentry::Cron::MonitorConfig.from_crontab(parsed_cron.original))
           end
 
           true
diff --git a/sentry-sidekiq/spec/fixtures/sidekiq-cron-schedule.yml b/sentry-sidekiq/spec/fixtures/sidekiq-cron-schedule.yml
index 65b5945a6..fe2798262 100644
--- a/sentry-sidekiq/spec/fixtures/sidekiq-cron-schedule.yml
+++ b/sentry-sidekiq/spec/fixtures/sidekiq-cron-schedule.yml
@@ -6,6 +6,10 @@ manual:
   cron: "* * * * *"
   class: "SadWorkerWithCron"
 
+human_readable_cron:
+  cron: "every 5 minutes"
+  class: HappyWorkerWithHumanReadableCron
+
 invalid_cron:
   cron: "not a crontab"
   class: "ReportingWorker"
diff --git a/sentry-sidekiq/spec/sentry/sidekiq/cron/job_spec.rb b/sentry-sidekiq/spec/sentry/sidekiq/cron/job_spec.rb
index 44f02f86e..c0f223096 100644
--- a/sentry-sidekiq/spec/sentry/sidekiq/cron/job_spec.rb
+++ b/sentry-sidekiq/spec/sentry/sidekiq/cron/job_spec.rb
@@ -10,6 +10,7 @@
   before do
     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 })
     # sidekiq-cron 2.0+ accepts second argument to `load_from_hash!` with options,
     # such as {source: 'schedule'}, but sidekiq-cron 1.9.1 (last version to support Ruby 2.6) does not.
     # Since we're not using the source option in our code anyway, it's safe to not pass the 2nd arg.
@@ -48,6 +49,23 @@
     expect(HappyWorkerForCron.sentry_monitor_config.schedule.value).to eq('* * * * *')
   end
 
+  it 'patches HappyWorkerWithHumanReadableCron' do
+    expect(HappyWorkerWithHumanReadableCron.ancestors).to include(Sentry::Cron::MonitorCheckIns)
+    expect(HappyWorkerWithHumanReadableCron.sentry_monitor_slug).to eq('human_readable_cron')
+    expect(HappyWorkerWithHumanReadableCron.sentry_monitor_config).to be_a(Sentry::Cron::MonitorConfig)
+    expect(HappyWorkerWithHumanReadableCron.sentry_monitor_config.schedule).to be_a(Sentry::Cron::MonitorSchedule::Crontab)
+    expect(HappyWorkerWithHumanReadableCron.sentry_monitor_config.schedule.value).to eq('*/5 * * * *')
+  end
+
+  it 'patches HappyWorkerWithSymbolName' do
+    expect(HappyWorkerWithSymbolName.ancestors).to include(Sentry::Cron::MonitorCheckIns)
+    expect(HappyWorkerWithSymbolName.sentry_monitor_slug).to eq('symbol_name')
+    expect(HappyWorkerWithSymbolName.sentry_monitor_config).to be_a(Sentry::Cron::MonitorConfig)
+    expect(HappyWorkerWithSymbolName.sentry_monitor_config.schedule).to be_a(Sentry::Cron::MonitorSchedule::Crontab)
+    expect(HappyWorkerWithSymbolName.sentry_monitor_config.schedule.value).to eq('* * * * *')
+  end
+
+
   it 'does not override SadWorkerWithCron manually set values' do
     expect(SadWorkerWithCron.ancestors).to include(Sentry::Cron::MonitorCheckIns)
     expect(SadWorkerWithCron.sentry_monitor_slug).to eq('failed_job')
diff --git a/sentry-sidekiq/spec/spec_helper.rb b/sentry-sidekiq/spec/spec_helper.rb
index 83e55d7da..6b2287957 100644
--- a/sentry-sidekiq/spec/spec_helper.rb
+++ b/sentry-sidekiq/spec/spec_helper.rb
@@ -139,6 +139,8 @@ class HappyWorkerForCron < HappyWorker; end
 class HappyWorkerForScheduler < HappyWorker; end
 class HappyWorkerForSchedulerWithTimezone < HappyWorker; end
 class EveryHappyWorker < HappyWorker; end
+class HappyWorkerWithHumanReadableCron < HappyWorker; end
+class HappyWorkerWithSymbolName < HappyWorker; end
 
 class HappyWorkerWithCron < HappyWorker
   include Sentry::Cron::MonitorCheckIns