diff --git a/app/models/csv_dumps/direct_to_s3.rb b/app/models/csv_dumps/direct_to_s3.rb
index 41dcca8fd..2cc500f1a 100644
--- a/app/models/csv_dumps/direct_to_s3.rb
+++ b/app/models/csv_dumps/direct_to_s3.rb
@@ -30,6 +30,19 @@ def put_file(gzip_file_path, compressed: true)
       )
     end
 
+    def put_file_with_retry(gzip_file_path, opts={}, num_retries=5)
+      attempts ||= 1
+      put_file(gzip_file_path, opts)
+    rescue UnencryptedBucket => e # do not retry this error
+      raise e
+    rescue => e # rubocop:disable Style/RescueStandardError
+      retry if (attempts += 1) <= num_retries
+
+      # ensure we raise unexpected errors once we've exhausted
+      # the number of retries to continute to surface these errors
+      raise e
+    end
+
     def storage_adapter(adapter='aws')
       return @storage_adapter if @storage_adapter
 
diff --git a/app/models/csv_dumps/dump_processor.rb b/app/models/csv_dumps/dump_processor.rb
index 96ee63126..c2e4d7260 100644
--- a/app/models/csv_dumps/dump_processor.rb
+++ b/app/models/csv_dumps/dump_processor.rb
@@ -34,7 +34,7 @@ def perform_dump
 
     def upload_dump
       gzip_file_path = csv_dump.gzip!
-      write_to_s3(gzip_file_path)
+      write_to_object_store(gzip_file_path)
       set_ready_state
     end
 
@@ -49,8 +49,8 @@ def set_ready_state
       medium.save!
     end
 
-    def write_to_s3(gzip_file_path)
-      medium.put_file(gzip_file_path, compressed: true)
+    def write_to_object_store(gzip_file_path)
+      medium.put_file_with_retry(gzip_file_path, compressed: true)
     end
   end
 end
diff --git a/app/models/medium.rb b/app/models/medium.rb
index 663c4d070..41fb1fba4 100644
--- a/app/models/medium.rb
+++ b/app/models/medium.rb
@@ -82,12 +82,24 @@ def get_url(opts = {})
   end
 
   def put_file(file_path, opts={})
-    if file_path.blank?
-      raise MissingPutFilePath.new("Must specify a file_path to store")
-    end
+    raise MissingPutFilePath, 'Must specify a file_path to store' if file_path.blank?
+
     MediaStorage.put_file(src, file_path, indifferent_attributes.merge(opts))
   end
 
+  def put_file_with_retry(file_path, opts={}, num_retries=5)
+    attempts ||= 1
+    put_file(file_path, opts)
+  rescue MissingPutFilePath => e # do not retry these invalid put_file args
+    raise e
+  rescue => e # rubocop:disable Style/RescueStandardError
+    retry if (attempts += 1) <= num_retries
+
+    # ensure we raise unexpected errors once we've exhausted
+    # the number of retries to continute to surface these errors
+    raise e
+  end
+
   private
 
   def queue_medium_removal
diff --git a/spec/models/csv_dumps/direct_to_s3_spec.rb b/spec/models/csv_dumps/direct_to_s3_spec.rb
index 70488b97a..ee9898fb7 100644
--- a/spec/models/csv_dumps/direct_to_s3_spec.rb
+++ b/spec/models/csv_dumps/direct_to_s3_spec.rb
@@ -54,6 +54,35 @@
       end
     end
 
+    describe '#put_file_with_retry' do
+      it 'calls put_file with the src and other attributes' do
+        allow(adapter).to receive(:put_file)
+        direct_to_s3.put_file_with_retry(file_path)
+        expect(adapter).to have_received(:put_file).with(s3_path, file_path, s3_opts)
+      end
+
+      it 'retries the correct number of times' do
+        allow(adapter).to receive(:put_file).and_raise(Faraday::ConnectionFailed, 'some error in aws lib')
+        direct_to_s3.put_file_with_retry(file_path)
+      rescue Faraday::ConnectionFailed
+        expect(adapter).to have_received(:put_file).with(s3_path, file_path, s3_opts).exactly(5).times
+      end
+
+      it 'allows the retry number to be modified at runtime' do
+        allow(adapter).to receive(:put_file).and_raise(Faraday::ConnectionFailed, 'Connection reset by peer')
+        direct_to_s3.put_file_with_retry(file_path, {}, 2)
+      rescue Faraday::ConnectionFailed
+        expect(adapter).to have_received(:put_file).with(s3_path, file_path, s3_opts).twice
+      end
+
+      it 'does not retry if put_file raises UnencryptedBucket' do
+        allow(direct_to_s3).to receive(:put_file).and_raise(CsvDumps::DirectToS3::UnencryptedBucket)
+        direct_to_s3.put_file_with_retry('')
+      rescue CsvDumps::DirectToS3::UnencryptedBucket
+        expect(direct_to_s3).to have_received(:put_file).once
+      end
+    end
+
     describe 'bucket encryption' do
       it "raises an error if it's not encrypted" do
         allow(adapter).to receive(:encrypted_bucket?).and_return(false)
diff --git a/spec/models/csv_dumps/dump_processor_spec.rb b/spec/models/csv_dumps/dump_processor_spec.rb
index 626f52fa4..1710ab1b3 100644
--- a/spec/models/csv_dumps/dump_processor_spec.rb
+++ b/spec/models/csv_dumps/dump_processor_spec.rb
@@ -3,7 +3,7 @@
 RSpec.describe CsvDumps::DumpProcessor do
   let(:formatter) { double("Formatter", headers: false).tap { |f| allow(f).to receive(:to_rows) { |model| [model] } } }
   let(:scope) { [] }
-  let(:medium) { double("Medium", put_file: true, metadata: {}, save!: true) }
+  let(:medium) { instance_double('Medium', put_file_with_retry: true, metadata: {}, save!: true) }
   let(:csv_dump) { double(CsvDump, cleanup!: true, gzip!: true) }
   let(:processor) { described_class.new(formatter, scope, medium, csv_dump) }
 
@@ -29,14 +29,15 @@
     processor.execute
   end
 
-  it "push the file to s3" do
+  it 'push the file to an object store' do
     path = double
     allow(csv_dump).to receive(:gzip!).and_return(path)
-    expect(medium).to receive(:put_file).with(path, compressed: true).once
+    allow(medium).to receive(:put_file_with_retry)
     processor.execute
+    expect(medium).to have_received(:put_file_with_retry).with(path, compressed: true).once
   end
 
-  it "should clean up the file after sending to s3" do
+  it 'cleans up the file after sending to object store' do
     expect(csv_dump).to receive(:cleanup!).once
     processor.execute
   end
diff --git a/spec/models/medium_spec.rb b/spec/models/medium_spec.rb
index ba902c477..8ffe14fb9 100644
--- a/spec/models/medium_spec.rb
+++ b/spec/models/medium_spec.rb
@@ -180,6 +180,40 @@
     end
   end
 
+  describe '#put_file_with_retry' do
+    let(:file_path) { Rails.root.join('/tmp/project_x_dump.csv') }
+    let(:media_storage_put_file_params) do
+      [medium.src, file_path, medium.attributes]
+    end
+
+    it 'calls MediaStorage put_file with the src and other attributes' do
+      allow(MediaStorage).to receive(:put_file)
+      medium.put_file_with_retry(file_path)
+      expect(MediaStorage).to have_received(:put_file).with(*media_storage_put_file_params)
+    end
+
+    it 'retries the correct number of times' do
+      allow(MediaStorage).to receive(:put_file).and_raise(Faraday::ConnectionFailed, 'Connection reset by peer')
+      medium.put_file_with_retry(file_path)
+    rescue Faraday::ConnectionFailed
+      expect(MediaStorage).to have_received(:put_file).with(*media_storage_put_file_params).exactly(5).times
+    end
+
+    it 'allows the retry number to be modified at runtime' do
+      allow(MediaStorage).to receive(:put_file).and_raise(Faraday::ConnectionFailed, 'Connection reset by peer')
+      medium.put_file_with_retry(file_path, {}, 2)
+    rescue Faraday::ConnectionFailed
+      expect(MediaStorage).to have_received(:put_file).with(*media_storage_put_file_params).twice
+    end
+
+    it 'does not retry if put_file raises MissingPutFilePath' do
+      allow(medium).to receive(:put_file).and_call_original
+      medium.put_file_with_retry('')
+    rescue Medium::MissingPutFilePath
+      expect(medium).to have_received(:put_file).once
+    end
+  end
+
   describe "#locations" do
     let(:project) { create(:project) }
     context "when type is one of project_avatar, user_avatar, or project_background" do
diff --git a/spec/support/dump_worker.rb b/spec/support/dump_worker.rb
index abd0c9411..f9166f465 100644
--- a/spec/support/dump_worker.rb
+++ b/spec/support/dump_worker.rb
@@ -11,9 +11,10 @@
       worker.perform(another_project.id, "project")
     end
 
-    it "should not push a file to s3" do
-      expect(worker).to_not receive(:write_to_s3)
-      worker.perform(another_project.id, "project")
+    it 'does not write the file to a remote object store' do
+      allow(worker).to receive(:write_to_object_store)
+      worker.perform(another_project.id, 'project')
+      expect(worker).not_to have_received(:write_to_object_store)
     end
 
     it "should not queue a worker to send an email" do