diff --git a/lib/rollbar/notifier.rb b/lib/rollbar/notifier.rb
index c48be05c..9631ffdd 100644
--- a/lib/rollbar/notifier.rb
+++ b/lib/rollbar/notifier.rb
@@ -211,7 +211,9 @@ def process_item(item)
       end
     rescue StandardError => e
       log_error("[Rollbar] Error processing the item: #{e.class}, #{e.message}. Item: #{item.payload.inspect}")
-      raise e
+      raise e unless via_failsafe?(item)
+
+      log_error('[Rollbar] Item has already failed. Not re-raising')
     end
 
     # We will reraise exceptions in this method so async queues
@@ -772,5 +774,9 @@ def log_instance_link(data)
       uuid_url = Util.uuid_rollbar_url(data, configuration)
       log_info "[Rollbar] Details: #{uuid_url} (only available if report was successful)"
     end
+
+    def via_failsafe?(item)
+      item.payload.fetch('data', {}).fetch(:failsafe, false)
+    end
   end
 end
diff --git a/spec/dummyapp/app/assets/config/manifest.js b/spec/dummyapp/app/assets/config/manifest.js
new file mode 100644
index 00000000..e69de29b
diff --git a/spec/rollbar/notifier_spec.rb b/spec/rollbar/notifier_spec.rb
index 7e0b9aaf..9c1e77da 100644
--- a/spec/rollbar/notifier_spec.rb
+++ b/spec/rollbar/notifier_spec.rb
@@ -1,5 +1,6 @@
 require 'rollbar'
 require 'rollbar/notifier'
+require 'spec_helper'
 
 describe Rollbar::Notifier do
   describe '#scope' do
@@ -41,6 +42,82 @@
     end
   end
 
+  describe '#process_item' do
+    subject(:process_item) { notifier.process_item(item) }
+    let(:notifier) { described_class.new }
+    let(:payload) { { :foo => :bar } }
+    let(:item) { Rollbar::Item.build_with(payload) }
+    let(:logger) { double(Logger).as_null_object }
+
+    before { notifier.configuration.logger = logger }
+
+    context 'when configured to write' do
+      before { notifier.configuration.write_to_file = true }
+
+      let(:dummy_file) { double(File).as_null_object }
+
+      it 'writes to the file' do
+        allow(File).to receive(:open).with(nil, 'a').and_return(dummy_file)
+
+        process_item
+
+        expect(dummy_file).to have_received(:puts).with(payload.to_json)
+      end
+    end
+
+    context 'when configured not to write' do
+      before do
+        notifier.configuration.write_to_file = false
+
+        allow(File).to receive(:open).with(nil, 'a').and_return(dummy_file)
+        allow(Net::HTTP).to receive(:new).and_return(dummy_http)
+        allow(::Rollbar).to receive(:log_error)
+      end
+
+      let(:dummy_file) { double(File).as_null_object }
+      let(:dummy_http) { double(Net::HTTP).as_null_object }
+
+      it 'does not write to the file' do
+        process_item
+
+        expect(dummy_file).not_to have_received(:puts).with(item)
+      end
+
+      it 'attempts to send via HTTP' do
+        process_item
+
+        expect(dummy_http).to have_received(:request)
+      end
+
+      context 'a socket error occurs' do
+        before { allow(dummy_http).to receive(:request).and_raise(SocketError) }
+
+        it 'passes the message on' do
+          expect {process_item}.to raise_error(SocketError)
+        end
+
+        context 'the item has come via failsafe' do
+          let(:exception) { SocketError.new('original exception') }
+          let(:payload) { notifier.send_failsafe('the failure', exception) }
+
+          it 'does not pass the message on' do
+            expect { process_item }.to_not raise_error
+          end
+        end
+      end
+    end
+  end
+
+  describe '#send_failsafe' do
+    subject(:send_failsafe) { described_class.new.send_failsafe(message, exception) }
+    let(:message) { 'testing failsafe' }
+    let(:exception) { StandardError.new }
+
+    it 'sets a flag on the payload so we know the payload has come through this way' do
+      expect(send_failsafe['data']).to include(:failsafe => true)
+    end
+  end
+
   if RUBY_PLATFORM == 'java'
     describe '#extract_arguments' do
       # See https://docs.oracle.com/javase/8/docs/api/java/lang/Throwable.html