diff --git a/CHANGELOG.md b/CHANGELOG.md
index 1388a7da2..37b3c8d37 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -3,6 +3,15 @@
 ### Features
 
 - Record client reports for profiles [#2107](https://github.com/getsentry/sentry-ruby/pull/2107)
+- Add `Sentry.capture_check_in` API for Cron Monitoring [#2117](https://github.com/getsentry/sentry-ruby/pull/2117)
+
+  You can now track progress of long running scheduled jobs.
+
+  ```rb
+  check_in_id = Sentry.capture_check_in('job_name', :in_progress)
+  # do job stuff
+  Sentry.capture_check_in('job_name', :ok, check_in_id: check_in_id)
+  ```
 
 ### Bug Fixes
 
diff --git a/sentry-ruby/lib/sentry-ruby.rb b/sentry-ruby/lib/sentry-ruby.rb
index daed11803..8d0ce7c18 100644
--- a/sentry-ruby/lib/sentry-ruby.rb
+++ b/sentry-ruby/lib/sentry-ruby.rb
@@ -15,6 +15,7 @@
 require "sentry/event"
 require "sentry/error_event"
 require "sentry/transaction_event"
+require "sentry/check_in_event"
 require "sentry/span"
 require "sentry/transaction"
 require "sentry/hub"
@@ -430,6 +431,19 @@ def capture_event(event)
       get_current_hub.capture_event(event)
     end
 
+    # Captures a check-in and sends it to Sentry via the currently active hub.
+    #
+    # @param slug [String] identifier of this monitor
+    # @param status [Symbol] status of this check-in, one of Sentry::CheckInEvent::VALID_STATUSES
+    # @yieldparam scope [Scope]
+    # TODO-neel-crons yard @option
+    #
+    # @return [String, nil]
+    def capture_check_in(slug, status, **options, &block)
+      return unless initialized?
+      get_current_hub.capture_check_in(slug, status, **options, &block)
+    end
+
     # Takes or initializes a new Sentry::Transaction and makes a sampling decision for it.
     #
     # @return [Transaction, nil]
diff --git a/sentry-ruby/lib/sentry/check_in_event.rb b/sentry-ruby/lib/sentry/check_in_event.rb
new file mode 100644
index 000000000..d2b266aa3
--- /dev/null
+++ b/sentry-ruby/lib/sentry/check_in_event.rb
@@ -0,0 +1,60 @@
+# frozen_string_literal
+
+require 'securerandom'
+require 'sentry/cron/monitor_config'
+
+module Sentry
+  class CheckInEvent < Event
+    TYPE = 'check_in'
+
+    # uuid to identify this check-in.
+    # @return [String]
+    attr_accessor :check_in_id
+
+    # Identifier of the monitor for this check-in.
+    # @return [String]
+    attr_accessor :monitor_slug
+
+    # Duration of this check since it has started in seconds.
+    # @return [Integer, nil]
+    attr_accessor :duration
+
+    # Monitor configuration to support upserts.
+    # @return [Cron::MonitorConfig, nil]
+    attr_accessor :monitor_config
+
+    # Status of this check-in.
+    # @return [Symbol]
+    attr_accessor :status
+
+    VALID_STATUSES = %i(ok in_progress error)
+
+    def initialize(
+      slug:,
+      status:,
+      duration: nil,
+      monitor_config: nil,
+      check_in_id: nil,
+      **options
+    )
+      super(**options)
+
+      self.monitor_slug = slug
+      self.status = status
+      self.duration = duration
+      self.monitor_config = monitor_config
+      self.check_in_id = check_in_id || SecureRandom.uuid.delete('-')
+    end
+
+    # @return [Hash]
+    def to_hash
+      data = super
+      data[:check_in_id] = check_in_id
+      data[:monitor_slug] = monitor_slug
+      data[:status] = status
+      data[:duration] = duration if duration
+      data[:monitor_config] = monitor_config.to_hash if monitor_config
+      data
+    end
+  end
+end
diff --git a/sentry-ruby/lib/sentry/client.rb b/sentry-ruby/lib/sentry/client.rb
index 80f1165c8..67320133b 100644
--- a/sentry-ruby/lib/sentry/client.rb
+++ b/sentry-ruby/lib/sentry/client.rb
@@ -104,6 +104,33 @@ def event_from_message(message, hint = {}, backtrace: nil)
       event
     end
 
+    # Initializes a CheckInEvent object with the given options.
+    # @param slug [String] identifier of this monitor
+    # @param status [Symbol] status of this check-in, one of Sentry::CheckInEvent::VALID_STATUSES
+    # @param hint [Hash] the hint data that'll be passed to `before_send` callback and the scope's event processors.
+    # TODO-neel-crons yard opts
+    # @return [Event]
+    def event_from_check_in(
+      slug,
+      status,
+      hint = {},
+      duration: nil,
+      monitor_config: nil,
+      check_in_id: nil
+    )
+      return unless configuration.sending_allowed?
+
+      CheckInEvent.new(
+        configuration: configuration,
+        integration_meta: Sentry.integrations[hint[:integration]],
+        slug: slug,
+        status: status,
+        duration: duration,
+        monitor_config: monitor_config,
+        check_in_id: check_in_id
+      )
+    end
+
     # Initializes an Event object with the given Transaction object.
     # @param transaction [Transaction] the transaction to be recorded.
     # @return [TransactionEvent]
diff --git a/sentry-ruby/lib/sentry/cron/monitor_config.rb b/sentry-ruby/lib/sentry/cron/monitor_config.rb
new file mode 100644
index 000000000..791631e32
--- /dev/null
+++ b/sentry-ruby/lib/sentry/cron/monitor_config.rb
@@ -0,0 +1,43 @@
+# frozen_string_literal
+
+require 'sentry/cron/monitor_schedule'
+
+module Sentry
+  module Cron
+    class MonitorConfig
+      # The monitor schedule configuration
+      # @return [MonitorSchedule::Crontab, MonitorSchedule::Interval]
+      attr_accessor :schedule
+
+      # How long (in minutes) after the expected checkin time will we wait
+      # until we consider the checkin to have been missed.
+      # @return [Integer, nil]
+      attr_accessor :checkin_margin
+
+      # How long (in minutes) is the checkin allowed to run for in in_progress
+      # before it is considered failed.
+      # @return [Integer, nil]
+      attr_accessor :max_runtime
+
+      # tz database style timezone string
+      # @return [String, nil]
+      attr_accessor :timezone
+
+      def initialize(schedule, checkin_margin: nil, max_runtime: nil, timezone: nil)
+        @schedule = schedule
+        @checkin_margin = checkin_margin
+        @max_runtime = max_runtime
+        @timezone = timezone
+      end
+
+      def to_hash
+        {
+          schedule: schedule.to_hash,
+          checkin_margin: checkin_margin,
+          max_runtime: max_runtime,
+          timezone: timezone
+        }.compact
+      end
+    end
+  end
+end
diff --git a/sentry-ruby/lib/sentry/cron/monitor_schedule.rb b/sentry-ruby/lib/sentry/cron/monitor_schedule.rb
new file mode 100644
index 000000000..e23615b59
--- /dev/null
+++ b/sentry-ruby/lib/sentry/cron/monitor_schedule.rb
@@ -0,0 +1,42 @@
+# frozen_string_literal
+
+module Sentry
+  module Cron
+    module MonitorSchedule
+      class Crontab
+        # A crontab formatted string such as "0 * * * *".
+        # @return [String]
+        attr_accessor :value
+
+        def initialize(value)
+          @value = value
+        end
+
+        def to_hash
+          { type: :crontab, value: value }
+        end
+      end
+
+      class Interval
+        # The number representing duration of the interval.
+        # @return [Integer]
+        attr_accessor :value
+
+        # The unit representing duration of the interval.
+        # @return [Symbol]
+        attr_accessor :unit
+
+        VALID_UNITS = %i(year month week day hour minute)
+
+        def initialize(value, unit)
+          @value = value
+          @unit = unit
+        end
+
+        def to_hash
+          { type: :interval, value: value, unit: unit }
+        end
+      end
+    end
+  end
+end
diff --git a/sentry-ruby/lib/sentry/hub.rb b/sentry-ruby/lib/sentry/hub.rb
index 7d9dca4c7..36258eb33 100644
--- a/sentry-ruby/lib/sentry/hub.rb
+++ b/sentry-ruby/lib/sentry/hub.rb
@@ -156,6 +156,30 @@ def capture_message(message, **options, &block)
       capture_event(event, **options, &block)
     end
 
+    def capture_check_in(slug, status, **options, &block)
+      check_argument_type!(slug, ::String)
+      check_argument_includes!(status, Sentry::CheckInEvent::VALID_STATUSES)
+
+      return unless current_client
+
+      options[:hint] ||= {}
+      options[:hint][:slug] = slug
+
+      event = current_client.event_from_check_in(
+        slug,
+        status,
+        options[:hint],
+        duration: options.delete(:duration),
+        monitor_config: options.delete(:monitor_config),
+        check_in_id: options.delete(:check_in_id)
+      )
+
+      return unless event
+
+      capture_event(event, **options, &block)
+      event.check_in_id
+    end
+
     def capture_event(event, **options, &block)
       check_argument_type!(event, Sentry::Event)
 
@@ -178,7 +202,7 @@ def capture_event(event, **options, &block)
         configuration.log_debug(event.to_json_compatible)
       end
 
-      @last_event_id = event&.event_id unless event.is_a?(Sentry::TransactionEvent)
+      @last_event_id = event&.event_id if event.is_a?(Sentry::ErrorEvent)
       event
     end
 
diff --git a/sentry-ruby/lib/sentry/integrable.rb b/sentry-ruby/lib/sentry/integrable.rb
index daa3669f7..a1edeadb6 100644
--- a/sentry-ruby/lib/sentry/integrable.rb
+++ b/sentry-ruby/lib/sentry/integrable.rb
@@ -22,5 +22,11 @@ def capture_message(message, **options, &block)
       options[:hint][:integration] = integration_name
       Sentry.capture_message(message, **options, &block)
     end
+
+    def capture_check_in(slug, status, **options, &block)
+      options[:hint] ||= {}
+      options[:hint][:integration] = integration_name
+      Sentry.capture_check_in(slug, status, **options, &block)
+    end
   end
 end
diff --git a/sentry-ruby/lib/sentry/utils/argument_checking_helper.rb b/sentry-ruby/lib/sentry/utils/argument_checking_helper.rb
index 5b161b872..e00eb5fc2 100644
--- a/sentry-ruby/lib/sentry/utils/argument_checking_helper.rb
+++ b/sentry-ruby/lib/sentry/utils/argument_checking_helper.rb
@@ -9,5 +9,11 @@ def check_argument_type!(argument, *expected_types)
         raise ArgumentError, "expect the argument to be a #{expected_types.join(' or ')}, got #{argument.class} (#{argument.inspect})"
       end
     end
+
+    def check_argument_includes!(argument, values)
+      unless values.include?(argument)
+        raise ArgumentError, "expect the argument to be one of #{values.map(&:inspect).join(' or ')}, got #{argument.inspect}"
+      end
+    end
   end
 end