diff --git a/CHANGELOG.md b/CHANGELOG.md
index 7c8c5af..3d6d5a6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,15 @@
 # Changelog
 
+## 1.0.0
+### Breaking Changes
+- This library will fail to load if `Delayed::Worker.destroy_failed_jobs` is set to true.
+  Delayed::Job sets this option to true by default, you will need to configure it to false
+  in order to include this library.
+### Changes
+- Moves `on_cancellation` logic from the before delayed job lifecycle hook to the after hook.
+- Wrapped the job group cancel hook in a lock to prevent concurrently failing jobs from enqueueing
+  multiple on cancellation jobs.
+
 ## 0.14.0
 - Reverts changes made in version 0.13.
 
diff --git a/README.md b/README.md
index 74be389..f68eba3 100644
--- a/README.md
+++ b/README.md
@@ -35,6 +35,15 @@ Run the required database migrations:
     $ rails generate delayed_job_groups_plugin:install
     $ rake db:migrate
 
+## Upgrading from 0.14.0
+
+This library is now incompatible with Delayed::Job's default setting for `destroy_failed_jobs`.
+In order to use Delayed Job Groups, you must set it to false while configuring Delayed::Job:
+
+```ruby
+Delayed::Worker.destroy_failed_jobs = false
+```
+
 ## Upgrading from 0.1.2
 run the following generator to create a migration for the new configuration column.
 
@@ -42,6 +51,7 @@ run the following generator to create a migration for the new configuration colu
     # add `default: true, null: false` to the generated migration for the failure_cancels_group column
     $ rake db:migrate
 
+
 ## Usage
 
 Creating a job group and queueing some jobs:
diff --git a/lib/delayed/job_groups/errors.rb b/lib/delayed/job_groups/errors.rb
new file mode 100644
index 0000000..ee0393f
--- /dev/null
+++ b/lib/delayed/job_groups/errors.rb
@@ -0,0 +1,16 @@
+# frozen_string_literal: true
+
+module Delayed
+  module JobGroups
+    ConfigurationError = Class.new(StandardError)
+
+    class IncompatibleWithDelayedJobError < ConfigurationError
+      DEFAULT_MESSAGE = 'DelayedJobGroupsPlugin is incompatible with Delayed::Job ' \
+                        'when `destroy_failed_jobs` is set to `true`'
+
+      def initialize(msg = DEFAULT_MESSAGE)
+        super(msg)
+      end
+    end
+  end
+end
diff --git a/lib/delayed/job_groups/job_group.rb b/lib/delayed/job_groups/job_group.rb
index e719b4d..68954f5 100644
--- a/lib/delayed/job_groups/job_group.rb
+++ b/lib/delayed/job_groups/job_group.rb
@@ -62,8 +62,18 @@ def unblock
       end
 
       def cancel
-        Delayed::Job.enqueue(on_cancellation_job, on_cancellation_job_options || {}) if on_cancellation_job
-        destroy
+        with_lock do
+          return if destroyed?
+
+          Delayed::Job.enqueue(on_cancellation_job, on_cancellation_job_options || {}) if on_cancellation_job
+          destroy
+        end
+      rescue ActiveRecord::RecordNotFound
+        # The first failing job to attempt cancelling the job group will enqueue the
+        # on cancellation job and destroy the group. Any other concurrently failing job
+        # in the same group can therefore silently return if the job group has already
+        # been destroyed.
+        nil
       end
 
       def check_for_completion(skip_pending_jobs_check: false)
diff --git a/lib/delayed/job_groups/plugin.rb b/lib/delayed/job_groups/plugin.rb
index 99495bc..48b07eb 100644
--- a/lib/delayed/job_groups/plugin.rb
+++ b/lib/delayed/job_groups/plugin.rb
@@ -17,7 +17,13 @@ def job.max_attempts
           end
         end
 
-        lifecycle.before(:failure) do |_worker, job|
+        # In order to allow individual jobs in the JobGroup to perform cleanup activities upon
+        # job failure, a JobGroups on cancellation job must be enqueued in the after failure
+        # delayed job lifecycle hook. If both were to be performed in the same hook, the job's
+        # failure hook and the on cancellation job may run at the same time since hook execution
+        # order is never guaranteed. This is particular important if the on cancellation job
+        # depends on state set in the failure hook of an individual job.
+        lifecycle.after(:failure) do |_worker, job|
           # If a job in the job group fails, then cancel the whole job group.
           # Need to check that the job group is present since another
           # job may have concurrently cancelled it.
diff --git a/lib/delayed/job_groups/railtie.rb b/lib/delayed/job_groups/railtie.rb
index 7a7a210..efb39ca 100644
--- a/lib/delayed/job_groups/railtie.rb
+++ b/lib/delayed/job_groups/railtie.rb
@@ -4,6 +4,17 @@ module Delayed
   module JobGroups
     class Railtie < ::Rails::Railtie
       config.after_initialize do
+
+        # On cancellation checks are performed in the after failure delayed job lifecycle, however
+        # https://github.com/collectiveidea/delayed_job/blob/master/lib/delayed/worker.rb#L268 may
+        # delete jobs before the hook runs. This could cause a successful job in the same group to
+        # complete the group instead of the group being cancelled. Therefore, we must ensure that
+        # the Delayed::Worker.destroy_failed_jobs is set to false, guaranteeing that the group is
+        # never empty if failure occurs.
+        if Delayed::Worker.destroy_failed_jobs && ActiveRecord::Base.connection.table_exists?(:delayed_job_groups)
+          raise Delayed::JobGroups::IncompatibleWithDelayedJobError
+        end
+
         Delayed::Backend::ActiveRecord::Job.include(Delayed::JobGroups::JobExtensions)
       end
     end
diff --git a/lib/delayed/job_groups/version.rb b/lib/delayed/job_groups/version.rb
index 674b79d..c6ece2a 100644
--- a/lib/delayed/job_groups/version.rb
+++ b/lib/delayed/job_groups/version.rb
@@ -2,6 +2,6 @@
 
 module Delayed
   module JobGroups
-    VERSION = '0.14.0'
+    VERSION = '1.0.0'
   end
 end
diff --git a/lib/delayed_job_groups_plugin.rb b/lib/delayed_job_groups_plugin.rb
index 5179ed7..52d8663 100644
--- a/lib/delayed_job_groups_plugin.rb
+++ b/lib/delayed_job_groups_plugin.rb
@@ -4,6 +4,7 @@
 require 'active_record'
 require 'delayed_job'
 require 'delayed_job_active_record'
+require 'delayed/job_groups/errors'
 require 'delayed/job_groups/compatibility'
 require 'delayed/job_groups/complete_stuck_job_groups_job'
 require 'delayed/job_groups/job_extensions'
@@ -18,6 +19,7 @@
 else
   # Do the same as in the railtie
   Delayed::Backend::ActiveRecord::Job.include(Delayed::JobGroups::JobExtensions)
+  raise Delayed::JobGroups::IncompatibleWithDelayedJobError if Delayed::Worker.destroy_failed_jobs
 end
 
 Delayed::Worker.plugins << Delayed::JobGroups::Plugin
diff --git a/lib/generators/delayed_job_groups_plugin/install_generator.rb b/lib/generators/delayed_job_groups_plugin/install_generator.rb
index 8b9767d..3c77b80 100644
--- a/lib/generators/delayed_job_groups_plugin/install_generator.rb
+++ b/lib/generators/delayed_job_groups_plugin/install_generator.rb
@@ -18,5 +18,37 @@ def self.next_migration_number(dirname)
       ActiveRecord::Generators::Base.next_migration_number(dirname)
     end
 
+    def create_initializer
+      initializer_file = File.join('config/initializers', 'delayed_job_config.rb')
+      configuration_on_matcher = /Delayed::Worker\.destroy_failed_jobs\s*=\s*true/
+      configuration_off_matcher = /Delayed::Worker\.destroy_failed_jobs\s*=\s*false/
+
+      say 'Attempting to initialize delayed_job_config initializer...', :green
+
+      if File.exist?(initializer_file)
+        say 'delayed_job_config initializer already exists... checking destroy_failed_jobs options', :green
+        contents = File.read(initializer_file)
+        if contents.match(configuration_on_matcher)
+          say 'Delayed::Worker.destroy_failed_jobs is set to true', :red
+          say 'This library requires the option to be set to false, updating config now!', :yellow
+
+          gsub_file initializer_file, configuration_on_matcher, 'Delayed::Worker.destroy_failed_jobs = false'
+        elsif contents.match(configuration_off_matcher)
+          say 'Delayed::Worker.destroy_failed_jobs is set to false; nothing to do!', :green
+        else
+          say 'Delayed::Worker.destroy_failed_jobs is not set'
+          say 'This library requires the option to be set to false, updating config now!', :yellow
+          inject_into_file initializer_file, "Delayed::Worker.destroy_failed_jobs = false\n"
+        end
+      else
+        create_file initializer_file do
+          <<~RUBY
+            # frozen_string_literal: true
+
+            Delayed::Worker.destroy_failed_jobs = false
+          RUBY
+        end
+      end
+    end
   end
 end
diff --git a/spec/delayed/job_groups/job_group_spec.rb b/spec/delayed/job_groups/job_group_spec.rb
index 92da6b3..7e5b7e4 100644
--- a/spec/delayed/job_groups/job_group_spec.rb
+++ b/spec/delayed/job_groups/job_group_spec.rb
@@ -299,11 +299,28 @@
   end
 
   describe "#cancel" do
+    subject(:job_group) do
+      create(
+        :job_group,
+        on_completion_job: on_completion_job,
+        on_completion_job_options: on_completion_job_options,
+        on_cancellation_job: on_cancellation_job,
+        on_cancellation_job_options: on_cancellation_job_options,
+        blocked: blocked
+      )
+    end
+
     let!(:queued_job) { Delayed::Job.create!(job_group_id: job_group.id) }
     let!(:running_job)  { Delayed::Job.create!(job_group_id: job_group.id, locked_at: Time.now, locked_by: 'test') }
+    let(:before_hook) {}
+    let(:on_cancellation_job) { 'dummy job' }
+    let(:on_cancellation_job_options) do
+      { foo: 'bar' }
+    end
+    let(:cancel) { true }
 
     before do
-      job_group.cancel
+      job_group.cancel if cancel
     end
 
     it "destroys the job group" do
@@ -317,6 +334,21 @@
     it "does not destroy running jobs" do
       expect(running_job).not_to have_been_destroyed
     end
+
+    context "when already cancelled" do
+      let(:cancel) { false }
+
+      it "skips cancel block if already cancelled" do
+        other = Delayed::JobGroups::JobGroup.find(job_group.id)
+        job_group.cancel
+
+        other.cancel
+        other.cancel
+
+        expect(Delayed::Job)
+          .to have_received(:enqueue).with(on_cancellation_job, on_cancellation_job_options).once
+      end
+    end
   end
 
   describe "#failure_cancels_group?" do
diff --git a/spec/spec_helper.rb b/spec/spec_helper.rb
index 16e4f2d..e50f64c 100644
--- a/spec/spec_helper.rb
+++ b/spec/spec_helper.rb
@@ -13,6 +13,11 @@
 
 require 'rspec/its'
 require 'database_cleaner'
+require 'delayed_job'
+
+Delayed::Worker.read_ahead = 1
+Delayed::Worker.destroy_failed_jobs = false
+
 require 'delayed_job_groups_plugin'
 require 'factory_bot'
 require 'yaml'
@@ -23,9 +28,6 @@
 
 FileUtils.makedirs('log')
 
-Delayed::Worker.read_ahead = 1
-Delayed::Worker.destroy_failed_jobs = false
-
 Delayed::Worker.logger = Logger.new('log/test.log')
 Delayed::Worker.logger.level = Logger::DEBUG
 ActiveRecord::Base.logger = Delayed::Worker.logger