diff --git a/config/initializers/sidekiq.rb b/config/initializers/sidekiq.rb
index 7b78b466a..a3800c5fc 100644
--- a/config/initializers/sidekiq.rb
+++ b/config/initializers/sidekiq.rb
@@ -1,4 +1,5 @@
 require Rails.root.join('lib/redis/config')
+require Rails.root.join('lib/captain_response_dequeued_logger')
 
 schedule_file = 'config/schedule.yml'
 
@@ -18,10 +19,10 @@ end
 Sidekiq.configure_server do |config|
   config.redis = Redis::Config.app
 
-  if ActiveModel::Type::Boolean.new.cast(ENV.fetch('ENABLE_SIDEKIQ_DEQUEUE_LOGGER', false))
-    config.server_middleware do |chain|
-      chain.add ChatwootDequeuedLogger
-    end
+  config.server_middleware do |chain|
+    chain.add CaptainResponseDequeuedLogger
+
+    chain.add ChatwootDequeuedLogger if ActiveModel::Type::Boolean.new.cast(ENV.fetch('ENABLE_SIDEKIQ_DEQUEUE_LOGGER', false))
   end
 
   # skip the default start stop logging
diff --git a/enterprise/app/jobs/captain/conversation/response_builder_job.rb b/enterprise/app/jobs/captain/conversation/response_builder_job.rb
index f37086816..45b6d9ad2 100644
--- a/enterprise/app/jobs/captain/conversation/response_builder_job.rb
+++ b/enterprise/app/jobs/captain/conversation/response_builder_job.rb
@@ -3,6 +3,7 @@ class Captain::Conversation::ResponseBuilderJob < ApplicationJob
   include Captain::Conversation::V1FalsePromiseHandler
   include Captain::Conversation::V2LifecycleEvents
   include Captain::Conversation::MessageBuilder
+  include Captain::Conversation::ResponseLifecycleLogging
 
   MAX_MESSAGE_LENGTH = 10_000
   retry_on ActiveStorage::FileNotFoundError, attempts: 3, wait: 2.seconds
@@ -14,12 +15,13 @@ class Captain::Conversation::ResponseBuilderJob < ApplicationJob
     @assistant = assistant
     @responding_to_message_id = responding_to_message_id if captain_v2_enabled?
 
-    return unless conversation_pending?
+    return log_non_pending unless conversation_pending?
 
     Current.executed_by = @assistant
 
     return generate_and_process_response unless captain_v2_enabled?
-    return if newer_customer_message_arrived?
+
+    return log_pre_generation_discard if newer_customer_message_arrived?
 
     generate_response_with_v2
   rescue ActiveStorage::FileNotFoundError, Faraday::BadRequestError => e
@@ -223,11 +225,6 @@ class Captain::Conversation::ResponseBuilderJob < ApplicationJob
     )
   end
 
-  def conversation_pending?
-    status = Conversation.uncached { Conversation.where(id: @conversation.id).pick(:status) }
-    status == 'pending' || status == Conversation.statuses[:pending]
-  end
-
   def newer_customer_message_arrived?
     return false if @responding_to_message_id.blank?
 
diff --git a/enterprise/app/services/captain/conversation/response_lifecycle_logging.rb b/enterprise/app/services/captain/conversation/response_lifecycle_logging.rb
new file mode 100644
index 000000000..b0ef5fcfa
--- /dev/null
+++ b/enterprise/app/services/captain/conversation/response_lifecycle_logging.rb
@@ -0,0 +1,24 @@
+module Captain::Conversation::ResponseLifecycleLogging
+  private
+
+  def conversation_pending?
+    @observed_conversation_status = Conversation.uncached { Conversation.where(id: @conversation.id).pick(:status) }
+    @observed_conversation_status == 'pending' || @observed_conversation_status == Conversation.statuses[:pending]
+  end
+
+  def log_non_pending
+    return if @responding_to_message_id.nil?
+
+    Rails.logger.info(
+      "[CAPTAIN][ResponseLifecycle] event=job_skipped reason=conversation_not_pending conversation_id=#{@conversation.id} " \
+      "responding_to_message_id=#{@responding_to_message_id} conversation_status=#{@observed_conversation_status}"
+    )
+  end
+
+  def log_pre_generation_discard
+    Rails.logger.info(
+      '[CAPTAIN][ResponseLifecycle] event=response_discarded reason=newer_customer_message_before_generation ' \
+      "conversation_id=#{@conversation.id} responding_to_message_id=#{@responding_to_message_id}"
+    )
+  end
+end
diff --git a/lib/captain_response_dequeued_logger.rb b/lib/captain_response_dequeued_logger.rb
new file mode 100644
index 000000000..7c61e5642
--- /dev/null
+++ b/lib/captain_response_dequeued_logger.rb
@@ -0,0 +1,26 @@
+# Records the Sidekiq fetch boundary for Captain response jobs without logging every job.
+class CaptainResponseDequeuedLogger
+  JOB_CLASS = 'Captain::Conversation::ResponseBuilderJob'.freeze
+
+  def call(_worker, job, queue)
+    log_dequeued(job, queue) if captain_v2_response_job?(job)
+    yield
+  end
+
+  private
+
+  def log_dequeued(job, queue)
+    active_job_id = job.dig('args', 0, 'job_id')
+    responding_to_message_id = job.dig('args', 0, 'arguments', 2)
+    Sidekiq.logger.info(
+      "[CAPTAIN][ResponseLifecycle] event=job_dequeued active_job_id=#{active_job_id} provider_job_id=#{job['jid']} " \
+      "responding_to_message_id=#{responding_to_message_id} queue=#{queue}"
+    )
+  end
+
+  def captain_v2_response_job?(job)
+    return false unless job['wrapped'] == JOB_CLASS
+
+    !job.dig('args', 0, 'arguments', 2).nil?
+  end
+end