diff --git a/lib/raygun.rb b/lib/raygun.rb
index 0c21fc8..ec85912 100644
--- a/lib/raygun.rb
+++ b/lib/raygun.rb
@@ -6,11 +6,6 @@
 require "rack"
 require "ostruct"
 
-begin
-  require "pry"
-rescue LoadError
-end
-
 require "raygun/version"
 require "raygun/configuration"
 require "raygun/client"
@@ -152,6 +147,8 @@ def track_exception_sync(exception_instance, env, user, retry_count)
         env[:custom_data] ||= {}
         env[:custom_data].merge!(original_stacktrace: exception_instance.backtrace)
 
+        ::Raygun::Breadcrumbs::Store.clear
+
         track_exception(new_exception, env, user, retry_count - 1)
       else
         raise e
diff --git a/lib/raygun/breadcrumbs/breadcrumb.rb b/lib/raygun/breadcrumbs/breadcrumb.rb
index 8395805..06f1ad8 100644
--- a/lib/raygun/breadcrumbs/breadcrumb.rb
+++ b/lib/raygun/breadcrumbs/breadcrumb.rb
@@ -25,6 +25,10 @@ def build_payload
           v != nil
         end]
       end
+
+      def size
+        return message.length + 100
+      end
     end
   end
 end
diff --git a/lib/raygun/breadcrumbs/store.rb b/lib/raygun/breadcrumbs/store.rb
index 3f1381d..505cd2f 100644
--- a/lib/raygun/breadcrumbs/store.rb
+++ b/lib/raygun/breadcrumbs/store.rb
@@ -47,6 +47,16 @@ def self.any?
         stored != nil && stored.length > 0
       end
 
+      def self.take_until_size(size)
+        breadcrumb_size = 0
+
+        stored.reverse.take_while do |crumb|
+          breadcrumb_size += crumb.size
+
+          breadcrumb_size < size
+        end.reverse
+      end
+
       private
 
       def self.should_record?(crumb)
diff --git a/lib/raygun/client.rb b/lib/raygun/client.rb
index 24a023a..3c09b4a 100644
--- a/lib/raygun/client.rb
+++ b/lib/raygun/client.rb
@@ -5,6 +5,7 @@ class Client
 
     ENV_IP_ADDRESS_KEYS = %w(action_dispatch.remote_ip raygun.remote_ip REMOTE_ADDR)
     NO_API_KEY_MESSAGE  = "[RAYGUN] Just a note, you've got no API Key configured, which means we can't report exceptions. Specify your Raygun API key using Raygun#setup (find yours at https://app.raygun.io)"
+    MAX_BREADCRUMBS_SIZE = 100_000
 
     include HTTParty
 
@@ -214,7 +215,7 @@ def build_payload_hash(exception_instance, env = {}, user = nil)
             }
         }
         store = ::Raygun::Breadcrumbs::Store
-        error_details[:breadcrumbs] = store.stored.map(&:build_payload) if store.any?
+        error_details[:breadcrumbs] = store.take_until_size(MAX_BREADCRUMBS_SIZE).map(&:build_payload) if store.any?
 
         Raygun.log('set details and breadcrumbs')
 
diff --git a/raygun4ruby.gemspec b/raygun4ruby.gemspec
index 66b173b..9f8f16d 100644
--- a/raygun4ruby.gemspec
+++ b/raygun4ruby.gemspec
@@ -37,7 +37,7 @@ Gem::Specification.new do |spec|
   spec.add_development_dependency "webmock"
 
   spec.add_development_dependency 'rails', "= 5.2"
-  spec.add_development_dependency 'sqlite3'
+  spec.add_development_dependency 'sqlite3', '~> 1.3.6'
   spec.add_development_dependency 'capybara'
   spec.add_development_dependency "rspec-rails"
   spec.add_development_dependency "launchy"
diff --git a/spec/raygun/breadcrumbs/breadcrumb_spec.rb b/spec/raygun/breadcrumbs/breadcrumb_spec.rb
index 67861b0..3f517aa 100644
--- a/spec/raygun/breadcrumbs/breadcrumb_spec.rb
+++ b/spec/raygun/breadcrumbs/breadcrumb_spec.rb
@@ -129,6 +129,43 @@ module Breadcrumbs
           expect(payload[:CustomData]).to eq(foo: 'bar')
         end
       end
+
+      describe "#size" do
+        before do
+          Timecop.freeze
+          Store.initialize
+        end
+        after do
+          Timecop.return
+          Store.clear
+        end
+
+        let(:message) { "This is a breadcrumb message" }
+
+        let(:breadcrumb) do
+          Store.record(
+            message: message,
+            category: "test",
+            level: :info,
+            class_name: "HomeController",
+            method_name: "index",
+            line_number: 17,
+            metadata: {
+              foo: 'bar'
+            }
+          )
+
+          Store.stored[0]
+        end
+
+        let(:size) { breadcrumb.size }
+
+        it "returns the estimated size of the breadcrumb" do
+          # Can't check all the fields but message so assume a standard 100 length for all of them
+          # The message should be the bulk of large breadcrumbs anyway
+          expect(size).to eq(message.length + 100)
+        end
+      end
     end
   end
 end
diff --git a/spec/raygun/breadcrumbs/store_spec.rb b/spec/raygun/breadcrumbs/store_spec.rb
index 7a9ce77..d3d457b 100644
--- a/spec/raygun/breadcrumbs/store_spec.rb
+++ b/spec/raygun/breadcrumbs/store_spec.rb
@@ -67,6 +67,30 @@ module Breadcrumbs
         end
       end
 
+      describe "#take_until_size" do
+        before do
+          subject.initialize
+        end
+
+        it "takes the most recent breadcrumbs until the size limit is reached" do
+          subject.record(message: '1' * 100)
+          subject.record(message: '2' * 100)
+          subject.record(message: '3' * 100)
+
+          crumbs = subject.take_until_size(500)
+
+          expect(crumbs.length).to eq(2)
+          expect(crumbs[0].message).to eq('2' * 100)
+          expect(crumbs[1].message).to eq('3' * 100)
+        end
+
+        it "does not crash with no recorded breadcrumbs" do
+          crumbs = subject.take_until_size(500)
+
+          expect(crumbs).to eq([])
+        end
+      end
+
       context "adding a breadcrumb" do
         class Foo
           include ::Raygun::Breadcrumbs