diff --git a/app/jobs/publish_feed_job.rb b/app/jobs/publish_feed_job.rb
index d1cfcd93d..d795a23c8 100644
--- a/app/jobs/publish_feed_job.rb
+++ b/app/jobs/publish_feed_job.rb
@@ -8,11 +8,18 @@ class PublishFeedJob < ApplicationJob
   attr_accessor :podcast, :episodes, :rss, :put_object, :copy_object
 
   def perform(podcast)
+    # Since we don't current have a way to retry failed attempts,
+    # and until somthing akin to https://github.com/PRX/feeder.prx.org/issues/714 lands
+    # the RSS publishing is extracted from the publishing pipeline semantics.
+    # TODO: recombine the publishing invocations (RSS, Apple) once we have some retry guarantees
+    podcast.feeds.each { |feed| save_file(podcast, feed) }
+
     PublishingPipelineState.start!(podcast)
     podcast.feeds.each { |feed| publish_feed(podcast, feed) }
     PublishingPipelineState.complete!(podcast)
   rescue => e
     PublishingPipelineState.error!(podcast)
+    Rails.logger.error("Error publishing podcast", {podcast_id: podcast.id, error: e.message, backtrace: e.backtrace.join("\n")})
     raise e
   ensure
     PublishingPipelineState.settle_remaining!(podcast)
@@ -39,9 +46,9 @@ def publish_apple(feed)
   end
 
   def publish_rss(podcast, feed)
-    res = save_file(podcast, feed)
+    # res = save_file(podcast, feed)
     PublishingPipelineState.publish_rss!(podcast)
-    res
+    # res
   end
 
   def save_file(podcast, feed, options = {})
diff --git a/app/models/apple/api_waiting.rb b/app/models/apple/api_waiting.rb
index ba9778c05..fc34d1378 100644
--- a/app/models/apple/api_waiting.rb
+++ b/app/models/apple/api_waiting.rb
@@ -8,12 +8,15 @@ module ApiWaiting
       def self.wait_for(remaining_records)
         t_beg = Time.now.utc
         loop do
-          # TODO: handle timeout
-          break [false, remaining_records] if Time.now.utc - t_beg > self::API_WAIT_TIMEOUT
+          Rails.logger.info(".wait_for", {remaining_records: remaining_records, have_waited: Time.now.utc - t_beg})
+
+          # Return `timeout == true` if we've waited too long
+          break [true, remaining_records] if Time.now.utc - t_beg > self::API_WAIT_TIMEOUT
 
           remaining_records = yield(remaining_records)
 
-          break [true, []] if remaining_records.empty?
+          # All done, return `timeout == false`
+          break [false, []] if remaining_records.empty?
 
           sleep(self::API_WAIT_INTERVAL)
         end
diff --git a/app/models/apple/episode.rb b/app/models/apple/episode.rb
index d55ca38ea..9808d11c9 100644
--- a/app/models/apple/episode.rb
+++ b/app/models/apple/episode.rb
@@ -25,13 +25,13 @@ def self.wait_for_asset_state(api, eps)
 
         remaining_eps.each do |ep|
           Rails.logger.info("Waiting for audio asset state?", {episode_id: ep.feeder_id,
-                                                                  delivery_file_count: ep.podcast_delivery_files.count,
-                                                                  delivery_files_processed_errors: ep.podcast_delivery_files.all?(&:processed_errors?),
-                                                                  delivery_files_processed: ep.podcast_delivery_files.all?(&:processed?),
-                                                                  delivery_files_delivered: ep.podcast_delivery_files.all?(&:delivered?),
-                                                                  asset_state: ep.audio_asset_state,
-                                                                  has_podcast_audio: ep&.podcast_container&.has_podcast_audio?,
-                                                                  waiting_for_asset_state: ep.waiting_for_asset_state?})
+                                                               delivery_file_count: ep.podcast_delivery_files.count,
+                                                               delivery_files_processed_errors: ep.podcast_delivery_files.all?(&:processed_errors?),
+                                                               delivery_files_processed: ep.podcast_delivery_files.all?(&:processed?),
+                                                               delivery_files_delivered: ep.podcast_delivery_files.all?(&:delivered?),
+                                                               asset_state: ep.audio_asset_state,
+                                                               has_podcast_audio: ep&.podcast_container&.has_podcast_audio?,
+                                                               waiting_for_asset_state: ep.waiting_for_asset_state?})
         end
 
         rem =
diff --git a/app/models/apple/publisher.rb b/app/models/apple/publisher.rb
index 49e1b7555..e3eb38296 100644
--- a/app/models/apple/publisher.rb
+++ b/app/models/apple/publisher.rb
@@ -113,7 +113,11 @@ def wait_for_upload_processing(eps)
       Rails.logger.tagged("##{__method__}") do
         pdfs = eps.map(&:podcast_delivery_files).flatten
 
-        Apple::PodcastDeliveryFile.wait_for_delivery_files(api, pdfs)
+        (waiting_timed_out, _) = Apple::PodcastDeliveryFile.wait_for_delivery(api, pdfs)
+        raise "Timed out waiting for delivery" if waiting_timed_out
+
+        (waiting_timed_out, _) = Apple::PodcastDeliveryFile.wait_for_processing(api, pdfs)
+        raise "Timed out waiting for processing" if waiting_timed_out
 
         # Get the latest state of the podcast containers
         # which should include synced files
@@ -124,7 +128,9 @@ def wait_for_upload_processing(eps)
     def wait_for_asset_state(eps)
       Rails.logger.tagged("##{__method__}") do
         eps = eps.filter { |e| e.podcast_delivery_files.any?(&:api_marked_as_uploaded?) }
-        Apple::Episode.wait_for_asset_state(api, eps)
+
+        (waiting_timed_out, _) = Apple::Episode.wait_for_asset_state(api, eps)
+        raise "Timed out waiting for asset state" if waiting_timed_out
       end
     end
 
diff --git a/app/models/podcast.rb b/app/models/podcast.rb
index fd589f114..930eb6993 100644
--- a/app/models/podcast.rb
+++ b/app/models/podcast.rb
@@ -54,6 +54,7 @@ def self.by_prx_series(series)
   end
 
   def self.release!(options = {})
+    Rails.logger.info("Podcast.release! called")
     PublishingPipelineState.expire_pipelines!
     Episode.release_episodes!(options)
   end
diff --git a/app/models/publishing_pipeline_state.rb b/app/models/publishing_pipeline_state.rb
index 4e64f3c77..ec1b236e4 100644
--- a/app/models/publishing_pipeline_state.rb
+++ b/app/models/publishing_pipeline_state.rb
@@ -88,29 +88,40 @@ def self.most_recent_state(podcast)
   end
 
   def self.start_pipeline!(podcast)
-    PublishingQueueItem.ensure_queued!(podcast)
-    attempt!(podcast)
+    Rails.logger.tagged("PublishingPipeLineState.start_pipeline!") do
+      PublishingQueueItem.ensure_queued!(podcast)
+      attempt!(podcast)
+    end
   end
 
   # None of the methods that grab locks are threadsafe if we assume that
   # creating published artifacts is non-idempotent (e.g. creating remote Apple
   # resources)
   def self.attempt!(podcast, perform_later: true)
-    podcast.with_publish_lock do
-      next if PublishingQueueItem.unfinished_items(podcast).empty?
-      next if PublishingQueueItem.current_unfinished_item(podcast).present?
-
-      # Dedupe the work, grab the latest unfinished item in the queue
-      latest_unfinished_item = PublishingQueueItem.unfinished_items(podcast).first
-
-      PublishingPipelineState.create!(podcast: podcast, publishing_queue_item: latest_unfinished_item, status: :created)
-
-      if perform_later
-        Rails.logger.info("Scheduling PublishFeedJob for podcast #{podcast.id}", {podcast_id: podcast.id})
-        PublishFeedJob.perform_later(podcast)
-      else
-        Rails.logger.info("Performing PublishFeedJob for podcast #{podcast.id}", {podcast_id: podcast.id})
-        PublishFeedJob.perform_now(podcast)
+    Rails.logger.tagged("PublishingPipeLineState.attempt!") do
+      podcast.with_publish_lock do
+        if PublishingQueueItem.unfinished_items(podcast).empty?
+          Rails.logger.info("Unfinished items empty, nothing to do", podcast_id: podcast.id)
+          next
+        end
+        if (curr_running_item = PublishingQueueItem.current_unfinished_item(podcast))
+          Rails.logger.info("Podcast's PublishingQueueItem already has running pipeline", podcast_id: podcast.id, running_queue_item: curr_running_item.id)
+          next
+        end
+
+        # Dedupe the work, grab the latest unfinished item in the queue
+        latest_unfinished_item = PublishingQueueItem.unfinished_items(podcast).first
+
+        Rails.logger.info("Creating publishing pipeline for podcast #{podcast.id}", {podcast_id: podcast.id, queue_item_id: latest_unfinished_item.id})
+        PublishingPipelineState.create!(podcast: podcast, publishing_queue_item: latest_unfinished_item, status: :created)
+
+        if perform_later
+          Rails.logger.info("Scheduling PublishFeedJob for podcast #{podcast.id}", {podcast_id: podcast.id})
+          PublishFeedJob.perform_later(podcast)
+        else
+          Rails.logger.info("Performing PublishFeedJob for podcast #{podcast.id}", {podcast_id: podcast.id})
+          PublishFeedJob.perform_now(podcast)
+        end
       end
     end
   end
@@ -155,7 +166,9 @@ def self.expire_pipelines!
   end
 
   def self.settle_remaining!(podcast)
-    attempt!(podcast)
+    Rails.logger.tagged("PublishingPipeLineState.settle_remaining!") do
+      attempt!(podcast)
+    end
   end
 
   def self.complete?(podcast)
@@ -165,7 +178,9 @@ def self.complete?(podcast)
   def self.state_transition(podcast, to_state)
     podcast.with_publish_lock do
       pqi = PublishingQueueItem.current_unfinished_item(podcast)
+      curr_running_item = PublishingQueueItem.current_unfinished_item(podcast)
       if pqi.present?
+        Rails.logger.info("Transitioning podcast #{podcast.id} publishing pipeline to state #{to_state}", {podcast_id: podcast.id, to_state: to_state, running_queue_item: curr_running_item&.id})
         PublishingPipelineState.create!(podcast: podcast, publishing_queue_item: pqi, status: to_state)
       else
         Rails.logger.error("Podcast #{podcast.id} has no unfinished work, cannot transition state", {podcast_id: podcast.id, to_state: to_state})
diff --git a/app/models/publishing_queue_item.rb b/app/models/publishing_queue_item.rb
index f98af237c..2fe567288 100644
--- a/app/models/publishing_queue_item.rb
+++ b/app/models/publishing_queue_item.rb
@@ -18,6 +18,7 @@ def self.delivery_status
   end
 
   def self.ensure_queued!(podcast)
+    Rails.logger.info("Creating new PublishingQueueItem", {podcast_id: podcast.id})
     create!(podcast: podcast)
   end
 
diff --git a/test/models/apple/api_waiting_test.rb b/test/models/apple/api_waiting_test.rb
index e6ac4f8d9..dbac3278c 100644
--- a/test/models/apple/api_waiting_test.rb
+++ b/test/models/apple/api_waiting_test.rb
@@ -25,7 +25,7 @@ class TestTimeout
 
       step = 0
 
-      (finished_waiting, remaining) = TestWait.wait_for(records) do |remaining|
+      (timed_out, remaining) = TestWait.wait_for(records) do |remaining|
         rem = remaining.dup
 
         assert_equal intervals[step], rem
@@ -37,16 +37,16 @@ class TestTimeout
         rem
       end
 
-      assert_equal finished_waiting, true
+      assert_equal timed_out, false
       assert_equal remaining, []
     end
 
     it "times out" do
-      (finished_waiting, remaining) = TestTimeout.wait_for(["a", "b", "c"]) do |remaining|
+      (timed_out, remaining) = TestTimeout.wait_for(["a", "b", "c"]) do |remaining|
         remaining
       end
 
-      assert_equal finished_waiting, false
+      assert_equal timed_out, true
       assert_equal remaining, ["a", "b", "c"]
     end
   end
diff --git a/test/models/publishing_pipeline_state_test.rb b/test/models/publishing_pipeline_state_test.rb
index 112668eab..de027e701 100644
--- a/test/models/publishing_pipeline_state_test.rb
+++ b/test/models/publishing_pipeline_state_test.rb
@@ -153,8 +153,8 @@
       assert_equal [pa1, pa2].sort, PublishingPipelineState.expired_pipelines.sort
       PublishingPipelineState.expire_pipelines!
 
-      assert_equal ["created", "expired"], PublishingPipelineState.latest_pipeline(podcast).map(&:status)
-      assert_equal ["created", "expired"], PublishingPipelineState.latest_pipeline(podcast2).map(&:status)
+      assert_equal ["created", "expired"].sort, PublishingPipelineState.latest_pipeline(podcast).map(&:status).sort
+      assert_equal ["created", "expired"].sort, PublishingPipelineState.latest_pipeline(podcast2).map(&:status).sort
 
       # All pipelines are in a terminal state
       # There is nothing running:
@@ -197,8 +197,10 @@
 
     describe "error!" do
       it 'sets the status to "error"' do
-        PublishFeedJob.stub_any_instance(:publish_feed, ->(*args) { raise "error" }) do
-          assert_raises(RuntimeError) { PublishingPipelineState.attempt!(podcast, perform_later: false) }
+        PublishFeedJob.stub_any_instance(:save_file, nil) do
+          PublishFeedJob.stub_any_instance(:publish_feed, ->(*args) { raise "error" }) do
+            assert_raises(RuntimeError) { PublishingPipelineState.attempt!(podcast, perform_later: false) }
+          end
         end
 
         assert_equal ["created", "started", "error"].sort, PublishingPipelineState.where(podcast: podcast).map(&:status).sort
@@ -207,8 +209,10 @@
 
     describe "complete!" do
       it 'sets the status to "complete"' do
-        PublishFeedJob.stub_any_instance(:publish_feed, "pub!") do
-          PublishingPipelineState.attempt!(podcast, perform_later: false)
+        PublishFeedJob.stub_any_instance(:save_file, nil) do
+          PublishFeedJob.stub_any_instance(:publish_feed, "pub!") do
+            PublishingPipelineState.attempt!(podcast, perform_later: false)
+          end
         end
 
         assert_equal ["created", "started", "complete"].sort, PublishingPipelineState.where(podcast: podcast).map(&:status).sort
@@ -218,8 +222,10 @@
         # And another request comes along to publish:
         PublishingQueueItem.create!(podcast: podcast)
 
-        PublishFeedJob.stub_any_instance(:publish_feed, "pub!") do
-          PublishingPipelineState.attempt!(podcast, perform_later: false)
+        PublishFeedJob.stub_any_instance(:save_file, nil) do
+          PublishFeedJob.stub_any_instance(:publish_feed, "pub!") do
+            PublishingPipelineState.attempt!(podcast, perform_later: false)
+          end
         end
 
         PublishingQueueItem.create!(podcast: podcast)