diff --git a/app/jobs/publish_feed_job.rb b/app/jobs/publish_feed_job.rb
index d25f9e271..50a3f63c7 100644
--- a/app/jobs/publish_feed_job.rb
+++ b/app/jobs/publish_feed_job.rb
@@ -32,6 +32,12 @@ def publish_apple(podcast, feed)
     res = PublishAppleJob.do_perform(podcast.apple_config)
     PublishingPipelineState.publish_apple!(podcast)
     res
+  rescue Apple::AssetStateTimeoutError => e
+    # Not strictly a 'fail state' because we want to retry this job
+    PublishingPipelineState.error_apple!(podcast)
+    Rails.logger.send(e.log_level, e.message, {podcast_id: podcast.id})
+    NewRelic::Agent.notice_error(e)
+    raise e if podcast.apple_config.sync_blocks_rss
   rescue => e
     if podcast.apple_config.sync_blocks_rss
       fail_state(podcast, "apple", e)
@@ -49,16 +55,32 @@ def publish_rss(podcast, feed)
     fail_state(podcast, "rss", e)
   end
 
-  def fail_state(podcast, type, error)
-    (pipeline_method, log_level) = case type
-    when "apple" then [:error_apple!, :warn]
-    when "rss" then [:error_rss!, :warn]
-    when "apple_timeout", "error" then [:error!, :error]
+  def apple_timeout_log_level(error)
+    error.try(:log_level) || :error
+  end
+
+  def should_raise?(error)
+    if error.respond_to?(:raise_publishing_error?)
+      error.raise_publishing_error?
+    else
+      true
     end
+  end
+
+  def fail_state(podcast, type, error)
+    (pipeline_method, log_level) =
+      case type
+      when "apple" then [:error_apple!, :warn]
+      when "rss" then [:error_rss!, :warn]
+      when "apple_timeout"
+        level = apple_timeout_log_level(error)
+        [:retry!, level]
+      when "error" then [:error!, :error]
+      end
 
     PublishingPipelineState.public_send(pipeline_method, podcast)
     Rails.logger.send(log_level, error.message, {podcast_id: podcast.id})
-    raise error
+    raise error if should_raise?(error)
   end
 
   def save_file(podcast, feed, options = {})
diff --git a/app/models/apple/asset_state_timeout_error.rb b/app/models/apple/asset_state_timeout_error.rb
index 82e0b19b7..e90b7c10f 100644
--- a/app/models/apple/asset_state_timeout_error.rb
+++ b/app/models/apple/asset_state_timeout_error.rb
@@ -12,5 +12,20 @@ def initialize(episodes)
     def episode_ids
       episodes.map(&:feeder_id)
     end
+
+    def raise_publishing_error?
+      %i[error fatal].include?(log_level)
+    end
+
+    def log_level
+      case attempts
+      when 0..4
+        :warn
+      when 5
+        :error
+      else
+        :fatal
+      end
+    end
   end
 end
diff --git a/app/models/apple/episode_delivery_status.rb b/app/models/apple/episode_delivery_status.rb
index 5781c180c..24bf5bcfd 100644
--- a/app/models/apple/episode_delivery_status.rb
+++ b/app/models/apple/episode_delivery_status.rb
@@ -2,6 +2,18 @@ module Apple
   class EpisodeDeliveryStatus < ApplicationRecord
     belongs_to :episode, -> { with_deleted }, class_name: "::Episode"
 
+    def self.measure_asset_processing_duration(apple_episode_delivery_statuses)
+      statuses = apple_episode_delivery_statuses.to_a
+
+      last_status = statuses.shift
+      return nil unless last_status&.asset_processing_attempts.to_i.positive?
+
+      start_status = statuses.find { |status| status.asset_processing_attempts.to_i.zero? }
+      return nil unless start_status
+
+      Time.now - start_status.created_at
+    end
+
     def self.update_status(episode, attrs)
       new_status = (episode.apple_episode_delivery_status&.dup || default_status(episode))
       new_status.assign_attributes(attrs)
diff --git a/app/models/concerns/apple_delivery.rb b/app/models/concerns/apple_delivery.rb
index 0083481b7..3bf177e79 100644
--- a/app/models/concerns/apple_delivery.rb
+++ b/app/models/concerns/apple_delivery.rb
@@ -40,7 +40,7 @@ def apple_needs_delivery?
   end
 
   def apple_needs_delivery!
-    apple_update_delivery_status(delivered: false)
+    apple_update_delivery_status(delivered: false, asset_processing_attempts: 0)
   end
 
   def apple_has_delivery!
@@ -48,15 +48,7 @@ def apple_has_delivery!
   end
 
   def measure_asset_processing_duration
-    statuses = apple_episode_delivery_statuses.to_a
-
-    last_status = statuses.shift
-    return nil unless last_status&.asset_processing_attempts.to_i.positive?
-
-    start_status = statuses.find { |status| status.asset_processing_attempts.to_i.zero? }
-    return nil unless start_status
-
-    Time.now - start_status.created_at
+    Apple::EpisodeDeliveryStatus.measure_asset_processing_duration(apple_episode_delivery_statuses)
   end
 
   def apple_prepare_for_delivery!
diff --git a/app/models/publishing_pipeline_state.rb b/app/models/publishing_pipeline_state.rb
index 3fcb5baf7..5be1712bc 100644
--- a/app/models/publishing_pipeline_state.rb
+++ b/app/models/publishing_pipeline_state.rb
@@ -1,6 +1,6 @@
 class PublishingPipelineState < ApplicationRecord
-  TERMINAL_STATUSES = [:complete, :error, :expired].freeze
-  TERMINAL_FAILURE_STATUSES = [:error, :expired].freeze
+  TERMINAL_STATUSES = [:complete, :error, :expired, :retry].freeze
+  TERMINAL_FAILURE_STATUSES = [:error, :expired, :retry].freeze
   UNIQUE_STATUSES = TERMINAL_STATUSES + [:created, :started]
 
   # Handle the max timout for a publishing pipeline: Pub RSS job + Pub Apple job + a few extra minutes of flight
@@ -53,7 +53,8 @@ class PublishingPipelineState < ApplicationRecord
     :error,
     :expired,
     :error_apple,
-    :error_rss
+    :error_rss,
+    :retry
   ]
 
   validate :podcast_ids_match
@@ -170,6 +171,10 @@ def self.expire!(podcast)
     state_transition(podcast, :expired)
   end
 
+  def self.retry!(podcast)
+    state_transition(podcast, :retry)
+  end
+
   def self.expire_pipelines!
     Podcast.with_deleted.where(id: expired_pipelines.select(:podcast_id)).each do |podcast|
       Rails.logger.tagged("PublishingPipeLineState.expire_pipelines!", "Podcast:#{podcast.id}") do
diff --git a/test/jobs/publish_feed_job_test.rb b/test/jobs/publish_feed_job_test.rb
index f21445bbf..d3bead0c5 100644
--- a/test/jobs/publish_feed_job_test.rb
+++ b/test/jobs/publish_feed_job_test.rb
@@ -99,12 +99,16 @@
   end
 
   describe "publishing to apple" do
+    let(:podcast) { create(:podcast) }
+    let(:public_feed) { podcast.default_feed }
+    let(:private_feed) { create(:apple_feed, podcast: podcast) }
     let(:apple_feed) { private_feed }
-    let(:apple_config) { podcast.apple_config }
+    let(:apple_config) { private_feed.apple_config }
+    let(:apple_publisher) { apple_config.build_publisher }
 
     before do
       assert private_feed.persisted?
-      assert podcast.reload.apple_config.present?
+      assert apple_config.persisted?
     end
 
     describe "#perform" do
@@ -151,30 +155,55 @@
           PublishingQueueItem.create!(podcast: feed.podcast)
         end
 
-        it "raises an error if the apple publishing fails" do
+        let(:episode1) { build(:uploaded_apple_episode, show: apple_publisher.show) }
+        let(:episode2) { build(:uploaded_apple_episode, show: apple_publisher.show) }
+        let(:episodes) { [episode1, episode2] }
+
+        it "logs message if the apple publishing times out" do
           assert apple_feed.apple_config.present?
           assert apple_feed.apple_config.publish_enabled
 
-          PublishAppleJob.stub(:do_perform, ->(*, **) { raise "some apple error" }) do
-            assert_raises(RuntimeError) { PublishingPipelineState.attempt!(feed.podcast, perform_later: false) }
-
-            assert_equal ["created", "started", "error", "error_apple"].sort, PublishingPipelineState.where(podcast: feed.podcast).latest_pipelines.pluck(:status).sort
+          expected_level_for_timeouts = [
+            [0, 40],
+            [1, 40],
+            [2, 40],
+            [3, 40],
+            [4, 40],
+            [5, 50],
+            [6, 60]
+          ]
+
+          expected_level_for_timeouts.each do |(attempts, level)|
+            # simulate a episode waiting n times
+            episodes.first.apple_episode_delivery_status.update(asset_processing_attempts: attempts)
+
+            PublishFeedJob.stub(:s3_client, stub_client) do
+              PublishAppleJob.stub(:do_perform, ->(*, **) { raise Apple::AssetStateTimeoutError.new(episodes) }) do
+                lines = capture_json_logs do
+                  PublishingQueueItem.ensure_queued!(feed.podcast)
+                  PublishingPipelineState.attempt!(feed.podcast, perform_later: false)
+                rescue
+                  nil
+                end
+
+                log = lines.find { |l| l["msg"].include?("Timeout waiting for asset state change") }
+                assert log.present?
+                assert_equal level, log["level"]
+
+                assert_equal ["created", "started", "error_apple", "retry"], PublishingPipelineState.where(podcast: feed.podcast).latest_pipelines.order(:id).pluck(:status)
+              end
+            end
           end
         end
 
-        it "does not raise an error if the apple publishing fails and apple sync does not block rss publishing" do
+        it "raises an error if the apple publishing times out" do
           assert apple_feed.apple_config.present?
           assert apple_feed.apple_config.publish_enabled
-          apple_feed.apple_config.update!(sync_blocks_rss: false)
-          feed.reload
 
-          PublishFeedJob.stub(:s3_client, stub_client) do
-            PublishAppleJob.stub(:do_perform, ->(*, **) { raise "some apple error" }) do
-              # no error raised
-              PublishingPipelineState.attempt!(feed.podcast, perform_later: false)
+          PublishAppleJob.stub(:do_perform, ->(*, **) { raise Apple::AssetStateTimeoutError.new([]) }) do
+            assert_raises(Apple::AssetStateTimeoutError) { PublishingPipelineState.attempt!(feed.podcast, perform_later: false) }
 
-              assert_equal ["created", "started", "error_apple", "published_rss", "published_rss", "published_rss", "complete"].sort, PublishingPipelineState.where(podcast: feed.podcast).latest_pipelines.pluck(:status).sort
-            end
+            assert_equal ["created", "started", "error_apple", "retry"], PublishingPipelineState.where(podcast: feed.podcast).latest_pipelines.order(id: :asc).pluck(:status)
           end
         end
 
@@ -185,7 +214,23 @@
           PublishAppleJob.stub(:do_perform, ->(*, **) { raise Apple::AssetStateTimeoutError.new([]) }) do
             assert_raises(Apple::AssetStateTimeoutError) { PublishingPipelineState.attempt!(feed.podcast, perform_later: false) }
 
-            assert_equal ["created", "started", "error", "error_apple"].sort, PublishingPipelineState.where(podcast: feed.podcast).latest_pipelines.pluck(:status).sort
+            assert_equal ["created", "started", "error_apple", "retry"], PublishingPipelineState.where(podcast: feed.podcast).latest_pipelines.order(id: :asc).pluck(:status)
+          end
+        end
+
+        it "does not raise an error if the apple publishing fails and apple sync does not block rss publishing" do
+          assert apple_feed.apple_config.present?
+          assert apple_feed.apple_config.publish_enabled
+          apple_feed.apple_config.update!(sync_blocks_rss: false)
+          feed.reload
+
+          PublishFeedJob.stub(:s3_client, stub_client) do
+            PublishAppleJob.stub(:do_perform, ->(*, **) { raise "some apple error" }) do
+              # no error raised
+              PublishingPipelineState.attempt!(feed.podcast, perform_later: false)
+
+              assert_equal ["created", "started", "error_apple", "published_rss", "published_rss", "published_rss", "complete"].sort, PublishingPipelineState.where(podcast: feed.podcast).latest_pipelines.pluck(:status).sort
+            end
           end
         end
       end
diff --git a/test/models/publishing_pipeline_state_test.rb b/test/models/publishing_pipeline_state_test.rb
index 820524a6d..176a9b9f0 100644
--- a/test/models/publishing_pipeline_state_test.rb
+++ b/test/models/publishing_pipeline_state_test.rb
@@ -273,6 +273,41 @@
       end
     end
 
+    describe "retry!" do
+      let(:podcast) { create(:podcast) }
+      let(:public_feed) { podcast.default_feed }
+      let(:private_feed) { create(:apple_feed, podcast: podcast) }
+      let(:apple_feed) { private_feed }
+      let(:apple_config) { private_feed.apple_config }
+      let(:apple_publisher) { apple_config.build_publisher }
+
+      it 'sets the status to "retry"' do
+        episode = build(:uploaded_apple_episode, show: apple_publisher.show)
+
+        # it does not trigger an exception
+        episode.apple_episode_delivery_status.update(asset_processing_attempts: 1)
+
+        pqi = nil
+        PublishFeedJob.stub_any_instance(:save_file, nil) do
+          PublishAppleJob.stub(:do_perform, ->(*args) { raise Apple::AssetStateTimeoutError.new([episode]) }) do
+            pqi = PublishingQueueItem.ensure_queued!(podcast)
+            PublishingPipelineState.attempt!(podcast, perform_later: false)
+          end
+        end
+
+        assert_equal ["created", "started", "error_apple", "retry"], PublishingPipelineState.where(podcast: podcast).order(:id).pluck(:status)
+        assert_equal "retry", pqi.reload.last_pipeline_state
+
+        # it retries
+        PublishingPipelineState.retry_failed_pipelines!
+        assert_equal ["created", "started", "error_apple", "retry", "created"], PublishingPipelineState.where(podcast: podcast).order(:id).pluck(:status)
+        res_pqi = PublishingQueueItem.current_unfinished_item(podcast)
+
+        assert res_pqi.id > pqi.id
+        assert_equal "created", res_pqi.last_pipeline_state
+      end
+    end
+
     describe "complete!" do
       it 'sets the status to "complete"' do
         PublishFeedJob.stub_any_instance(:save_file, nil) do