diff --git a/.env b/.env
index 3dc380b571..5f791c9f76 100644
--- a/.env
+++ b/.env
@@ -21,12 +21,6 @@ CHECKOUT_ZONE="Australia"
 # Find currency codes at http://en.wikipedia.org/wiki/ISO_4217.
 CURRENCY="AUD"
 
-# The whenever gem can set the `MAILTO` variable for our cron jobs.
-# You can define an email address to notify if any job outputs something.
-# But you need a working mail server setup so that the message is delivered.
-# See: config/schedule.rb
-# SCHEDULE_NOTIFICATIONS="admin@example.com"
-
 # Mail settings
 MAIL_HOST="example.com"
 MAIL_DOMAIN="example.com"
diff --git a/Gemfile b/Gemfile
index 9fab20b216..2ec71d0b3c 100644
--- a/Gemfile
+++ b/Gemfile
@@ -118,8 +118,6 @@ gem 'immigrant'
 gem 'roo' # read spreadsheets
 gem 'spreadsheet_architect' # write spreadsheets
 
-gem 'whenever', require: false
-
 gem 'coffee-rails', '~> 5.0.0'
 
 gem 'angular_rails_csrf'
diff --git a/Gemfile.lock b/Gemfile.lock
index 946f98271b..d74b9dbeab 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -245,7 +245,6 @@ GEM
     cgi (0.5.1)
     childprocess (5.0.0)
     choice (0.2.0)
-    chronic (0.10.2)
     coderay (1.1.3)
     coffee-rails (5.0.0)
       coffee-script (>= 2.2.0)
@@ -968,8 +967,6 @@ GEM
       base64
       websocket-extensions (>= 0.1.0)
     websocket-extensions (0.1.5)
-    whenever (1.1.2)
-      chronic (>= 0.6.3)
     xml-simple (1.1.8)
     xpath (3.2.0)
       nokogiri (~> 1.8)
@@ -1127,7 +1124,6 @@ DEPENDENCIES
   web!
   web-console
   webmock
-  whenever
   wicked_pdf!
   wkhtmltopdf-binary!
 
diff --git a/app/jobs/rake_job.rb b/app/jobs/rake_job.rb
new file mode 100644
index 0000000000..07f89b72e8
--- /dev/null
+++ b/app/jobs/rake_job.rb
@@ -0,0 +1,15 @@
+# frozen_string_literal: true
+
+require "rake"
+
+# Executes a rake task
+class RakeJob < ApplicationJob
+  def perform(task_string)
+    Rails.application.load_tasks if Rake::Task.tasks.empty?
+
+    Rake.application.invoke_task(task_string)
+  ensure
+    name, _args = Rake.application.parse_task_string(task_string)
+    Rake::Task[name].reenable
+  end
+end
diff --git a/config/initializers/sidekiq.rb b/config/initializers/sidekiq.rb
index 0628c9e409..25bf4bb557 100644
--- a/config/initializers/sidekiq.rb
+++ b/config/initializers/sidekiq.rb
@@ -7,6 +7,15 @@ redis_connection_settings = {
 
 Sidekiq.configure_server do |config|
   config.redis = redis_connection_settings
+  config.on(:startup) do
+    # Load schedule file similar to sidekiq/cli.rb loading the main config.
+    path = File.expand_path("../sidekiq_scheduler.yml", __dir__)
+    erb = ERB.new(File.read(path), trim_mode: "-")
+
+    Sidekiq.schedule =
+      YAML.safe_load(erb.result, permitted_classes: [Symbol], aliases: true)
+    SidekiqScheduler::Scheduler.instance.reload_schedule!
+  end
 end
 
 Sidekiq.configure_client do |config|
diff --git a/config/schedule.rb b/config/schedule.rb
deleted file mode 100644
index 20c240f5ff..0000000000
--- a/config/schedule.rb
+++ /dev/null
@@ -1,24 +0,0 @@
-# Force manual loading of rails application to get all env variables from dotenv-rails when running whenever cmd
-require File.expand_path('../environment',  __FILE__)
-
-require 'whenever'
-require 'yaml'
-
-# Learn more: http://github.com/javan/whenever
-
-env "MAILTO", ENV["SCHEDULE_NOTIFICATIONS"] if ENV["SCHEDULE_NOTIFICATIONS"]
-
-# If we use -e with a file containing specs, rspec interprets it and filters out our examples
-job_type :run_file, "cd :path; :environment_variable=:environment bundle exec script/rails runner :task :output"
-
-every 1.month, at: '4:30am' do
-  rake 'ofn:data:remove_transient_data'
-end
-
-every 1.day, at: '2:45am' do
-  rake 'db2fog:clean' if ENV['S3_BACKUPS_BUCKET']
-end
-
-every 4.hours do
-  rake 'db2fog:backup' if ENV['S3_BACKUPS_BUCKET']
-end
diff --git a/config/sidekiq.yml b/config/sidekiq.yml
index bcd4e31909..3be6e166dc 100644
--- a/config/sidekiq.yml
+++ b/config/sidekiq.yml
@@ -7,15 +7,8 @@
   - default
   - mailers
 
-:scheduler:
-  :schedule:
-    HeartbeatJob:
-      every: ["5m", first_in: "0s"]
-    SubscriptionPlacementJob:
-      every: "5m"
-    SubscriptionConfirmJob:
-      every: "5m"
-    TriggerOrderCyclesToOpenJob:
-      every: "5m"
-    OrderCycleClosingJob:
-      every: "5m"
+# This config is loaded by sidekiq before dotenv is loading our server config.
+# Therefore we load the schedule later. See:
+#
+# - config/initializers/sidekiq.rb
+# - config/sidekiq_scheduler.yml
diff --git a/config/sidekiq_scheduler.yml b/config/sidekiq_scheduler.yml
new file mode 100644
index 0000000000..29ef3a7e76
--- /dev/null
+++ b/config/sidekiq_scheduler.yml
@@ -0,0 +1,36 @@
+# Configure sidekiq-scheduler to run jobs.
+#
+# - https://github.com/sidekiq-scheduler/sidekiq-scheduler
+#
+# > Note that every and interval count from when the Sidekiq process (re)starts.
+# > So every: '48h' will never run if the Sidekiq process is restarted daily,
+# > for example. You can do every: ['48h', first_in: '0s'] to make the job run
+# > immediately after a restart, and then have the worker check when it was
+# > last run.
+#
+# Therefore, we use `cron` for jobs that should run at certain times like backups.
+HeartbeatJob:
+  every: ["5m", first_in: "0s"]
+SubscriptionPlacementJob:
+  every: "5m"
+SubscriptionConfirmJob:
+  every: "5m"
+TriggerOrderCyclesToOpenJob:
+  every: "5m"
+OrderCycleClosingJob:
+  every: "5m"
+
+backup:
+  class: "RakeJob"
+  args: ["db2fog:backup"]
+  cron: "0 */4 * * *" # every 4 hours
+  enabled: <%= ENV.fetch("S3_BACKUPS_BUCKET", false) && true %>
+backup_clean:
+  class: "RakeJob"
+  args: ["db2fog:clean"]
+  cron: "45 2 * * *" # every day at 2:45am
+  enabled: <%= ENV.fetch("S3_BACKUPS_BUCKET", false) && true %>
+ofn_clean:
+  class: "RakeJob"
+  args: ["ofn:data:remove_transient_data"]
+  cron: "30 4 1 * *" # every month on the first at 4:30am
diff --git a/spec/jobs/rake_job_spec.rb b/spec/jobs/rake_job_spec.rb
new file mode 100644
index 0000000000..9430c116d4
--- /dev/null
+++ b/spec/jobs/rake_job_spec.rb
@@ -0,0 +1,18 @@
+# frozen_string_literal: true
+
+require "tasks/data/remove_transient_data"
+
+RSpec.describe RakeJob do
+  let(:task_string) { "ofn:data:remove_transient_data" }
+
+  it "calls the removal service" do
+    expect(RemoveTransientData).to receive(:new).and_call_original
+    RakeJob.perform_now(task_string)
+  end
+
+  it "can be called several times" do
+    expect(RemoveTransientData).to receive(:new).twice.and_call_original
+    RakeJob.perform_now(task_string)
+    RakeJob.perform_now(task_string)
+  end
+end