diff --git a/lib/rollbar.rb b/lib/rollbar.rb
index 06376a67..ac8a63b3 100644
--- a/lib/rollbar.rb
+++ b/lib/rollbar.rb
@@ -237,7 +237,7 @@ def process_from_async_handler(payload)
       end
     end
 
-    def send_failsafe(message, exception)
+    def send_failsafe(message, exception, uuid = nil, host = nil)
       exception_reason = failsafe_reason(message, exception)
 
       log_error "[Rollbar] Sending failsafe response due to #{exception_reason}"
@@ -256,6 +256,10 @@ def send_failsafe(message, exception)
           :name => 'rollbar-gem',
           :version => VERSION
         },
+        :custom => {
+          :orig_uuid => uuid,
+          :orig_host => host
+        },
         :internal => true,
         :failsafe => true
       }
diff --git a/lib/rollbar/item.rb b/lib/rollbar/item.rb
index 0a424eba..c2012e8f 100644
--- a/lib/rollbar/item.rb
+++ b/lib/rollbar/item.rb
@@ -101,16 +101,24 @@ def dump
       # from an async handler job, which can be serialized.
       stringified_payload = Util::Hash.deep_stringify_keys(payload)
       result = Truncation.truncate(stringified_payload)
+
       return result unless Truncation.truncate?(result)
 
-      original_size = Rollbar::JSON.dump(payload).bytesize
-      final_size = result.bytesize
-      notifier.send_failsafe("Could not send payload due to it being too large after truncating attempts. Original size: #{original_size} Final size: #{final_size}", nil)
-      logger.error("[Rollbar] Payload too large to be sent: #{Rollbar::JSON.dump(payload)}")
+      handle_too_large_payload(stringified_payload, result)
 
       nil
     end
 
+    def handle_too_large_payload(stringified_payload, final_payload)
+      original_size = Rollbar::JSON.dump(stringified_payload).bytesize
+      final_size = final_payload.bytesize
+      uuid = stringified_payload['data']['uuid']
+      host = stringified_payload['data']['server']['host']
+
+      notifier.send_failsafe("Could not send payload due to it being too large after truncating attempts. Original size: #{original_size} Final size: #{final_size}", nil, uuid, host)
+      logger.error("[Rollbar] Payload too large to be sent for UUID #{uuid}: #{Rollbar::JSON.dump(payload)}")
+    end
+
     def ignored?
       data = payload['data']
 
diff --git a/lib/rollbar/truncation/frames_strategy.rb b/lib/rollbar/truncation/frames_strategy.rb
index af48c0aa..f470d741 100644
--- a/lib/rollbar/truncation/frames_strategy.rb
+++ b/lib/rollbar/truncation/frames_strategy.rb
@@ -1,4 +1,5 @@
 require 'rollbar/truncation/mixin'
+require 'rollbar/util'
 
 module Rollbar
   module Truncation
@@ -10,7 +11,7 @@ def self.call(payload)
       end
 
       def call(payload)
-        new_payload = payload.clone
+        new_payload = Rollbar::Util.deep_copy(payload)
         body = new_payload['data']['body']
 
         if body['trace_chain']
diff --git a/lib/rollbar/truncation/min_body_strategy.rb b/lib/rollbar/truncation/min_body_strategy.rb
index 140bd7cc..13446525 100644
--- a/lib/rollbar/truncation/min_body_strategy.rb
+++ b/lib/rollbar/truncation/min_body_strategy.rb
@@ -1,4 +1,5 @@
 require 'rollbar/truncation/mixin'
+require 'rollbar/util'
 
 module Rollbar
   module Truncation
@@ -10,7 +11,7 @@ def self.call(payload)
       end
 
       def call(payload)
-        new_payload = payload.clone
+        new_payload = Rollbar::Util.deep_copy(payload)
         body = new_payload['data']['body']
 
         if body['trace_chain']
diff --git a/lib/rollbar/truncation/strings_strategy.rb b/lib/rollbar/truncation/strings_strategy.rb
index 71c6e92c..608f829e 100644
--- a/lib/rollbar/truncation/strings_strategy.rb
+++ b/lib/rollbar/truncation/strings_strategy.rb
@@ -14,7 +14,7 @@ def self.call(payload)
 
       def call(payload)
         result = nil
-        new_payload = payload.clone
+        new_payload = Rollbar::Util.deep_copy(payload)
 
         STRING_THRESHOLDS.each do |threshold|
           truncate_proc = truncate_strings_proc(threshold)
diff --git a/spec/rollbar/item_spec.rb b/spec/rollbar/item_spec.rb
index 9dd69faf..c1e00bf8 100644
--- a/spec/rollbar/item_spec.rb
+++ b/spec/rollbar/item_spec.rb
@@ -646,8 +646,16 @@
       end
 
       it 'calls Notifier#send_failsafe and logs the error' do
-        expect(notifier).to receive(:send_failsafe)
-        expect(logger).to receive(:error)
+        original_size = Rollbar::JSON.dump(payload).bytesize
+        final_size = Rollbar::Truncation.truncate(payload.clone).bytesize
+        # final_size = original_size
+        rollbar_message = "Could not send payload due to it being too large after truncating attempts. Original size: #{original_size} Final size: #{final_size}"
+        uuid = payload['data']['uuid']
+        host = payload['data']['server']['host']
+        log_message = "[Rollbar] Payload too large to be sent for UUID #{uuid}: #{Rollbar::JSON.dump(payload)}"
+
+        expect(notifier).to receive(:send_failsafe).with(rollbar_message, nil, uuid, host)
+        expect(logger).to receive(:error).with(log_message)
 
         item.dump
       end
diff --git a/spec/rollbar/truncation/min_body_strategy_spec.rb b/spec/rollbar/truncation/min_body_strategy_spec.rb
index f0ba2b04..35f0e5ee 100644
--- a/spec/rollbar/truncation/min_body_strategy_spec.rb
+++ b/spec/rollbar/truncation/min_body_strategy_spec.rb
@@ -45,7 +45,7 @@
     end
 
     context 'with a message payload' do
-      let(:payload_fixture) { 'payloads/sample.trace_chain.json' }
+      let(:payload_fixture) { 'payloads/message.json' }
 
       it "doesn't truncate anything and returns same payload" do
         result = Rollbar::JSON.load(described_class.call(payload))
diff --git a/spec/rollbar_spec.rb b/spec/rollbar_spec.rb
index be78be7a..5847f495 100644
--- a/spec/rollbar_spec.rb
+++ b/spec/rollbar_spec.rb
@@ -1222,6 +1222,18 @@ def backtrace
         expect(sent_payload['data'][:body][:message][:body]).to be_eql(expected_body)
       end
     end
+
+    context 'with uuid and host' do
+      let(:host) { 'the-host' }
+      let(:uuid) { 'the-uuid' }
+      it 'sets the uuid and host in correct keys' do
+        sent_payload = notifier.send(:send_failsafe, 'testing uuid and host',
+                                     exception, uuid, host)
+
+        expect(sent_payload['data'][:custom][:orig_uuid]).to be_eql('the-uuid')
+        expect(sent_payload['data'][:custom][:orig_host]).to be_eql('the-host')
+      end
+    end
   end
 
   context 'when reporting internal error with nil context' do