diff --git a/CHANGELOG.md b/CHANGELOG.md
index e06511d..3b0e1f9 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,6 +10,7 @@ and releases in PushmiPullyu adheres to [Semantic Versioning](https://semver.org
 
 - Add rescue block to catch exceptions while waiting for next item [#280](https://github.com/ualbertalib/pushmi_pullyu/issues/280)
 - Add logic to fetch new community and collection information from jupiter and create their AIPS. [#255](https://github.com/ualbertalib/pushmi_pullyu/issues/255)
+- Add delay to re-ingestion attempts to allow for problems to be fixed [#297](https://github.com/ualbertalib/pushmi_pullyu/issues/297)
 - Bump git from 1.9.1 to 1.13.0
 ## [2.0.4] - 2022-11-22
 
diff --git a/README.md b/README.md
index 56c5b9d..115c9ba 100644
--- a/README.md
+++ b/README.md
@@ -66,7 +66,10 @@ Specific options:
   -W, --workdir PATH               Path for directory where AIP creation work takes place in
   -N, --process_name NAME          Name of the application process
   -m, --monitor                    Start monitor process for a deamon
-  -q, --queue NAME                 Name of the queue to read from
+  -q, --queue NAME                 Name of the queue to read from    
+  -i, --ingestion_prefix PREFIX    Prefix for keys used in counting the number of failed ingestion attempts
+  -x, --ingestion_attempts NUMBER  Max number of attempts to try ingesting an entity
+  -f, --first_failed_wait NUMBER   Time in seconds to wait after first failed entity deposit. This time will double every failed attempt
 
 Common options:
   -v, --version                    Show version
diff --git a/examples/pushmi_pullyu.yml b/examples/pushmi_pullyu.yml
index 3a07a35..3c6bc13 100644
--- a/examples/pushmi_pullyu.yml
+++ b/examples/pushmi_pullyu.yml
@@ -16,6 +16,9 @@ piddir: tmp/pids
 workdir: tmp/work
 process_name: pushmi_pullyu
 queue_name: dev:pmpy_queue
+ingestion_prefix: "'prod:pmpy_ingest_attempt:'" 
+ingestion_attempts: 15
+first_failed_wait: 10
 minimum_age: 0
 
 redis:
diff --git a/lib/pushmi_pullyu.rb b/lib/pushmi_pullyu.rb
index 83a923d..c7de3f3 100644
--- a/lib/pushmi_pullyu.rb
+++ b/lib/pushmi_pullyu.rb
@@ -26,6 +26,9 @@ module PushmiPullyu
     workdir: 'tmp/work',
     process_name: 'pushmi_pullyu',
     queue_name: 'dev:pmpy_queue',
+    ingestion_prefix: 'prod:pmpy_ingest_attempt:',
+    ingestion_attempts: 15,
+    first_failed_wait: 10,
     redis: {
       url: 'redis://localhost:6379'
     },
diff --git a/lib/pushmi_pullyu/cli.rb b/lib/pushmi_pullyu/cli.rb
index 5a62989..927d982 100644
--- a/lib/pushmi_pullyu/cli.rb
+++ b/lib/pushmi_pullyu/cli.rb
@@ -148,6 +148,21 @@ def parse_options(argv)
         opts[:queue_name] = queue
       end
 
+      o.on('-i', '--ingestion_prefix PREFIX',
+           'Prefix for keys used in counting the number of failed ingestion attempts') do |prefix|
+        opts[:ingestion_prefix] = prefix
+      end
+
+      o.on('-x', '--ingestion_attempts NUMBER', Integer,
+           'Max number of attempts to try ingesting an entity') do |ingestion_attempts|
+        opts[:ingestion_attempts] = ingestion_attempts
+      end
+
+      o.on('-f', '--first_failed_wait NUMBER', Integer,
+           'Time in seconds to wait after first failed deposit. Time will double every failed attempt') do |failed_wait|
+        opts[:first_failed_wait] = failed_wait
+      end
+
       o.separator ''
       o.separator 'Common options:'
 
@@ -183,16 +198,10 @@ def rotate_logs
 
   def run_preservation_cycle
     begin
-      entity_json = queue.wait_next_item
-      return unless entity_json
-
-      # jupiter is submitting the entries to reddis in a hash format using fat arrows. We need to change them to colons
-      # in order to parse them correctly from json
-      entity = JSON.parse(entity_json.gsub('=>', ':'), { symbolize_names: true })
-      return unless entity[:type].present? && entity[:uuid].present?
+      entity = queue.wait_next_item
+      return unless entity && entity[:type].present? && entity[:uuid].present?
     rescue StandardError => e
-      Rollbar.error(e)
-      logger.error(e)
+      log_exception(e)
     end
 
     # add additional information about the error context to errors that occur while processing this item.
@@ -209,7 +218,11 @@ def run_preservation_cycle
     # readding it to the queue as it will always fail
     rescue PushmiPullyu::AIP::EntityInvalid => e
     rescue StandardError => e
-      queue.add_entity_json(entity_json)
+      begin
+        queue.add_entity_in_timeframe(entity)
+      rescue MaxDepositAttemptsReached => e
+        log_exception(e)
+      end
 
     # rubocop:disable Lint/RescueException
     # Something other than a StandardError exception means something happened which we were not expecting!
@@ -218,8 +231,7 @@ def run_preservation_cycle
       raise e
     # rubocop:enable Lint/RescueException
     ensure
-      Rollbar.error(e)
-      logger.error(e)
+      log_exception(e)
     end
   end
 
@@ -294,4 +306,9 @@ def start_server_as_daemon
     end
   end
 
+  def log_exception(exception)
+    Rollbar.error(exception)
+    logger.error(exception)
+  end
+
 end
diff --git a/lib/pushmi_pullyu/preservation_queue.rb b/lib/pushmi_pullyu/preservation_queue.rb
index 236c160..5ecd679 100644
--- a/lib/pushmi_pullyu/preservation_queue.rb
+++ b/lib/pushmi_pullyu/preservation_queue.rb
@@ -20,6 +20,7 @@
 class PushmiPullyu::PreservationQueue
 
   class ConnectionError < StandardError; end
+  class MaxDepositAttemptsReached < StandardError; end
 
   def initialize(redis_url: 'redis://localhost:6379',
                  pool_opts: { size: 1, timeout: 5 },
@@ -50,7 +51,8 @@ def next_item
           rd.multi do |tx|
             tx.zrem(@queue_name, element) # remove the top element transactionally
           end
-          return element
+
+          return JSON.parse(element, { symbolize_names: true })
         else
           rd.unwatch # cancel the transaction since there was nothing in the queue
           return nil
@@ -68,12 +70,27 @@ def wait_next_item
     end
   end
 
-  def add_entity_json(entity_json)
+  def add_entity_in_timeframe(entity)
+    entity_attempts_key = "#{PushmiPullyu.options[:ingestion_prefix]}#{entity[:uuid]}"
+
     @redis.with do |connection|
-      connection.zadd @queue_name, Time.now.to_f, entity_json
+      # separate information for priority information and queue
+      deposit_attempt = connection.incr entity_attempts_key
+
+      if deposit_attempt <= PushmiPullyu.options[:ingestion_attempts]
+        connection.zadd @queue_name, Time.now.to_f + self.class.extra_wait_time(deposit_attempt),
+                        entity.slice(:uuid, :type).to_json
+      else
+        connection.del entity_attempts_key
+        raise MaxDepositAttemptsReached
+      end
     end
   end
 
+  def self.extra_wait_time(deposit_attempt)
+    (2**deposit_attempt) * PushmiPullyu.options[:first_failed_wait]
+  end
+
   protected
 
   def connected?
diff --git a/spec/fixtures/config.yml b/spec/fixtures/config.yml
index 31d986d..a3811f0 100644
--- a/spec/fixtures/config.yml
+++ b/spec/fixtures/config.yml
@@ -7,6 +7,9 @@ monitor: false
 piddir: tmp/spec/pids
 workdir: tmp/spec/work
 process_name: test_pushmi_pullyu
+ingestion_prefix: 'prod:pmpy_ingest_attempt:'
+ingestion_attempts: 15
+first_failed_wait: 10
 minimum_age: 1
 queue_name: test:pmpy_queue
 rollbar:
diff --git a/spec/integration/acceptance_spec.rb b/spec/integration/acceptance_spec.rb
index 5786428..0d823b2 100644
--- a/spec/integration/acceptance_spec.rb
+++ b/spec/integration/acceptance_spec.rb
@@ -39,11 +39,7 @@
     cli = PushmiPullyu::CLI.instance
     cli.parse(['-C', 'spec/fixtures/config.yml', '-W', workdir])
 
-    entity_json = JSON.parse(cli.send(:queue).wait_next_item)
-    entity = {
-      type: entity_json['type'],
-      uuid: entity_json['uuid']
-    }
+    entity = cli.send(:queue).wait_next_item
 
     expect(entity[:uuid]).to eq uuid
 
diff --git a/spec/pushmi_pullyu/cli_spec.rb b/spec/pushmi_pullyu/cli_spec.rb
index 24e70e8..190905e 100644
--- a/spec/pushmi_pullyu/cli_spec.rb
+++ b/spec/pushmi_pullyu/cli_spec.rb
@@ -1,5 +1,6 @@
 require 'spec_helper'
 require 'tempfile'
+require 'timecop'
 
 RSpec.describe PushmiPullyu::CLI do
   let(:cli) { PushmiPullyu::CLI.instance }
@@ -213,6 +214,9 @@
         expect(PushmiPullyu.options[:queue_name]).to eq 'test:pmpy_queue'
         expect(PushmiPullyu.options[:swift][:auth_url]).to eq 'http://127.0.0.1:8080/auth/v1.0'
         expect(PushmiPullyu.options[:rollbar][:token]).to eq 'abc123xyz'
+        expect(PushmiPullyu.options[:ingestion_prefix]).to eq 'prod:pmpy_ingest_attempt:'
+        expect(PushmiPullyu.options[:ingestion_attempts]).to eq 15
+        expect(PushmiPullyu.options[:first_failed_wait]).to eq 10
       end
 
       it 'still allows command line arguments to take precedence' do
@@ -220,7 +224,10 @@
                    '-C', 'spec/fixtures/config.yml',
                    '--logdir', 'path/to/random',
                    '--minimum-age', '5',
-                   '--piddir', 'path/to/piddir'])
+                   '--piddir', 'path/to/piddir',
+                   '--ingestion_prefix', 'prefix',
+                   '--ingestion_attempts', '20',
+                   '--first_failed_wait', '20'])
 
         expect(PushmiPullyu.options[:daemonize]).to be_truthy
         expect(PushmiPullyu.options[:config_file]).to eq 'spec/fixtures/config.yml'
@@ -230,6 +237,9 @@
         expect(PushmiPullyu.options[:piddir]).to eq 'path/to/piddir'
         expect(PushmiPullyu.options[:process_name]).to eq 'test_pushmi_pullyu'
         expect(PushmiPullyu.options[:minimum_age]).to be 5.0
+        expect(PushmiPullyu.options[:ingestion_prefix]).to eq 'prefix'
+        expect(PushmiPullyu.options[:ingestion_attempts]).to eq 20
+        expect(PushmiPullyu.options[:first_failed_wait]).to eq 20
       end
     end
 
@@ -273,11 +283,47 @@
         expect(old_options).to eq new_options
       end
 
-      it 'makes sure an entities information is readded to reddis when deposit fails' do
+      it 'delays the repeated attempts when deposits fail' do
+        # Lets substract 10 seconds to avoid waiting for the item to be processed
+        # expect((readded_entity_score.to_i - test_time).to_i).to eq 10
         cli.parse(['-C', 'spec/fixtures/config_wrong_swift.yml'])
         redis = Redis.new
-        redis.zadd(PushmiPullyu.options[:queue_name], 10,
-                   '{"uuid": "123e4567-e89b-12d3-a456-426614174000", "type": "items"}')
+        entity = { uuid: '123e4567-e89b-12d3-a456-426614174000', type: 'items' }
+
+        start_time = Time.now - 10
+        attempt_key = "#{PushmiPullyu.options[:ingestion_prefix]}#{entity[:uuid]}"
+        redis.zadd(PushmiPullyu.options[:queue_name], start_time.to_f, entity.to_json)
+        deposit_attempt = 0
+        redis.set(attempt_key, deposit_attempt)
+        Timecop.freeze do
+          while deposit_attempt < PushmiPullyu.options[:ingestion_attempts]
+            VCR.use_cassette('aip_download_and_swift_upload') do
+              PushmiPullyu::Logging.logger.fatal!
+              cli.send(:run_preservation_cycle)
+              PushmiPullyu::Logging.initialize_logger
+              time_now = Time.now.to_i
+              _readded_entity, readded_entity_score = redis.zrange(PushmiPullyu.options[:queue_name],
+                                                                   0, 0, with_scores: true).first
+              new_deposit_attempt = redis.get(attempt_key).to_i
+              extra_wait_time = PushmiPullyu::PreservationQueue.extra_wait_time(new_deposit_attempt)
+              # Make sure the deposits attempts are increasing by 1
+              expect(new_deposit_attempt).to eq deposit_attempt + 1
+              expect(readded_entity_score.to_i - time_now).to eq extra_wait_time
+              # We dont want to wait for defined minimum age so we add it to the time travel shenanigans
+              deposit_attempt = new_deposit_attempt
+              Timecop.travel(extra_wait_time + PushmiPullyu.options[:minimum_age])
+            end
+          end
+        end
+      end
+
+      it 'makes sure an entities information is readded to redis when deposit fails' do
+        cli.parse(['-C', 'spec/fixtures/config_wrong_swift.yml'])
+        redis = Redis.new
+        entity = { uuid: '123e4567-e89b-12d3-a456-426614174000', type: 'items' }
+
+        redis.zadd(PushmiPullyu.options[:queue_name], 10, entity.to_json)
+        redis.set("#{PushmiPullyu.options[:ingestion_prefix]}#{entity[:uuid]}", 0)
 
         original_entity_information, original_entity_score = redis.zrange(PushmiPullyu.options[:queue_name],
                                                                           0, 0, with_scores: true).first
@@ -291,10 +337,12 @@
           PushmiPullyu::Logging.initialize_logger
           readded_entity, readded_entity_score = redis.zrange(PushmiPullyu.options[:queue_name],
                                                               0, 0, with_scores: true).first
+          readded_attempt = redis.get("#{PushmiPullyu.options[:ingestion_prefix]}#{entity[:uuid]}")
           expect(original_entity_information).to eq readded_entity
           expect(original_entity_score).not_to eq readded_entity_score
+          expect(readded_attempt).to eq '1'
         end
-        redis.del(PushmiPullyu.options[:queue_name])
+        redis.flushall
       end
     end
   end
diff --git a/spec/pushmi_pullyu/preservation_queue_spec.rb b/spec/pushmi_pullyu/preservation_queue_spec.rb
index 03b437e..ce399f0 100644
--- a/spec/pushmi_pullyu/preservation_queue_spec.rb
+++ b/spec/pushmi_pullyu/preservation_queue_spec.rb
@@ -8,10 +8,10 @@
 
     before do
       PushmiPullyu.server_running = true
-      redis.zadd 'test:pmpy_queue', 1, 'noid1'
-      redis.zadd 'test:pmpy_queue', 3, 'noid3'
-      redis.zadd 'test:pmpy_queue', 4, 'noid2'
-      redis.zadd 'test:pmpy_queue', 10, 'noid1'
+      redis.zadd 'test:pmpy_queue', 1, '{"uuid":"9e3be94f-a5de-4589-96ca-b18efba280c1","type":"items"}'
+      redis.zadd 'test:pmpy_queue', 3, '{"uuid":"9e3be94f-a5de-4589-96ca-b18efba280c3","type":"items"}'
+      redis.zadd 'test:pmpy_queue', 4, '{"uuid":"9e3be94f-a5de-4589-96ca-b18efba280c2","type":"items"}'
+      redis.zadd 'test:pmpy_queue', 10, '{"uuid":"9e3be94f-a5de-4589-96ca-b18efba280c1","type":"items"}'
     end
 
     after do
@@ -19,9 +19,13 @@
     end
 
     it 'retrieves 3 items in priority order' do
-      expect(queue.wait_next_item).to eq 'noid3'
-      expect(queue.wait_next_item).to eq 'noid2'
-      expect(queue.wait_next_item).to eq 'noid1'
+      next_item = queue.wait_next_item
+
+      expect(next_item[:uuid]).to eq '9e3be94f-a5de-4589-96ca-b18efba280c3'
+      next_item = queue.wait_next_item
+      expect(next_item[:uuid]).to eq '9e3be94f-a5de-4589-96ca-b18efba280c2'
+      next_item = queue.wait_next_item
+      expect(next_item[:uuid]).to eq '9e3be94f-a5de-4589-96ca-b18efba280c1'
     end
   end
 
@@ -32,7 +36,7 @@
     let!(:redis) { Redis.new }
 
     before do
-      redis.zadd 'test:pmpy_queue', Time.now.to_f, 'noid1'
+      redis.zadd 'test:pmpy_queue', Time.now.to_f, '{"uuid":"9e3be94f-a5de-4589-96ca-b18efba280c1","type":"items"}'
     end
 
     after do
@@ -50,7 +54,7 @@
       expect(queue.next_item).to be_nil
 
       Timecop.travel(now + 15.minutes)
-      expect(queue.next_item).to eq 'noid1'
+      expect(queue.next_item[:uuid]).to eq '9e3be94f-a5de-4589-96ca-b18efba280c1'
     end
   end
 end