diff --git a/config/initializers/100-sidekiq.rb b/config/initializers/100-sidekiq.rb
index 211f667a3a6..958d0b91449 100644
--- a/config/initializers/100-sidekiq.rb
+++ b/config/initializers/100-sidekiq.rb
@@ -1,22 +1,108 @@
 # frozen_string_literal: true
 
-Rails.application.reloader.to_prepare do
-  require "sidekiq/pausable"
+require "sidekiq/pausable"
 
-  Sidekiq.configure_client do |config|
-    config.redis = Discourse.sidekiq_redis_config
+Sidekiq.configure_client do |config|
+  config.redis = Discourse.sidekiq_redis_config
+end
+
+Sidekiq.configure_server do |config|
+  config.redis = Discourse.sidekiq_redis_config
+
+  config.server_middleware do |chain|
+    chain.add Sidekiq::Pausable
+  end
+end
+
+if Sidekiq.server?
+
+  module Sidekiq
+    class CLI
+      private
+
+      def print_banner
+        # banner takes up too much space
+      end
+    end
   end
 
-  Sidekiq.configure_server do |config|
-    config.redis = Discourse.sidekiq_redis_config
+  # defer queue should simply run in sidekiq
+  Scheduler::Defer.async = false
 
-    config.server_middleware do |chain|
-      chain.add Sidekiq::Pausable
+  Rails.application.config.after_initialize do
+    # warm up AR
+    RailsMultisite::ConnectionManagement.safe_each_connection do
+      (ActiveRecord::Base.connection.tables - %w[schema_migrations versions]).each do |table|
+        table.classify.constantize.first rescue nil
+      end
+    end
+
+    scheduler_hostname = ENV["UNICORN_SCHEDULER_HOSTNAME"]
+
+    if !scheduler_hostname || scheduler_hostname.split(',').include?(Discourse.os_hostname)
+      begin
+        MiniScheduler.start(workers: GlobalSetting.mini_scheduler_workers)
+      rescue MiniScheduler::DistributedMutex::Timeout
+        sleep 5
+        retry
+      end
+    end
+  end
+end
+
+# Sidekiq#logger= applies patches to whichever logger we pass it.
+# Therefore something like Sidekiq.logger = Rails.logger will break
+# all logging in the application.
+#
+# Instead, this patch adds a dedicated logger instance and patches
+# the #add method to forward messages to Rails.logger.
+Sidekiq.logger = Logger.new(nil)
+Sidekiq.logger.define_singleton_method(:add) do |severity, message = nil, progname = nil, &blk|
+  Rails.logger.add(severity, message, progname, &blk)
+end
+
+class SidekiqLogsterReporter < Sidekiq::ExceptionHandler::Logger
+  def call(ex, context = {})
+
+    return if Jobs::HandledExceptionWrapper === ex
+    Discourse.reset_active_record_cache_if_needed(ex)
+
+    # Pass context to Logster
+    fake_env = {}
+    context.each do |key, value|
+      Logster.add_to_env(fake_env, key, value)
+    end
+
+    text = "Job exception: #{ex}\n"
+    if ex.backtrace
+      Logster.add_to_env(fake_env, :backtrace, ex.backtrace)
+    end
+
+    Logster.add_to_env(fake_env, :current_hostname, Discourse.current_hostname)
+
+    Thread.current[Logster::Logger::LOGSTER_ENV] = fake_env
+    Logster.logger.error(text)
+  rescue => e
+    Logster.logger.fatal("Failed to log exception #{ex} #{hash}\nReason: #{e.class} #{e}\n#{e.backtrace.join("\n")}")
+  ensure
+    Thread.current[Logster::Logger::LOGSTER_ENV] = nil
+  end
+end
+
+Sidekiq.error_handlers.clear
+Sidekiq.error_handlers << SidekiqLogsterReporter.new
+
+Sidekiq.strict_args!
+
+Rails.application.config.to_prepare do
+  # Ensure that scheduled jobs are loaded before mini_scheduler is configured.
+  if Rails.env.development?
+    Dir.glob("#{Rails.root}/app/jobs/scheduled/*.rb") do |f|
+      require(f)
     end
   end
 
   MiniScheduler.configure do |config|
-
     config.redis = Discourse.redis
 
     config.job_exception_handler do |ex, context|
@@ -34,86 +120,5 @@ Rails.application.reloader.to_prepare do
         db: RailsMultisite::ConnectionManagement::DEFAULT
       )
     end
-
   end
-
-  if Sidekiq.server?
-
-    module Sidekiq
-      class CLI
-        private
-
-        def print_banner
-          # banner takes up too much space
-        end
-      end
-    end
-
-    # defer queue should simply run in sidekiq
-    Scheduler::Defer.async = false
-
-    Rails.application.config.after_initialize do
-      # warm up AR
-      RailsMultisite::ConnectionManagement.safe_each_connection do
-        (ActiveRecord::Base.connection.tables - %w[schema_migrations versions]).each do |table|
-          table.classify.constantize.first rescue nil
-        end
-      end
-
-      scheduler_hostname = ENV["UNICORN_SCHEDULER_HOSTNAME"]
-
-      if !scheduler_hostname || scheduler_hostname.split(',').include?(Discourse.os_hostname)
-        begin
-          MiniScheduler.start(workers: GlobalSetting.mini_scheduler_workers)
-        rescue MiniScheduler::DistributedMutex::Timeout
-          sleep 5
-          retry
-        end
-      end
-    end
-  end
-
-  # Sidekiq#logger= applies patches to whichever logger we pass it.
-  # Therefore something like Sidekiq.logger = Rails.logger will break
-  # all logging in the application.
-  #
-  # Instead, this patch adds a dedicated logger instance and patches
-  # the #add method to forward messages to Rails.logger.
-  Sidekiq.logger = Logger.new(nil)
-  Sidekiq.logger.define_singleton_method(:add) do |severity, message = nil, progname = nil, &blk|
-    Rails.logger.add(severity, message, progname, &blk)
-  end
-
-  class SidekiqLogsterReporter < Sidekiq::ExceptionHandler::Logger
-    def call(ex, context = {})
-
-      return if Jobs::HandledExceptionWrapper === ex
-      Discourse.reset_active_record_cache_if_needed(ex)
-
-      # Pass context to Logster
-      fake_env = {}
-      context.each do |key, value|
-        Logster.add_to_env(fake_env, key, value)
-      end
-
-      text = "Job exception: #{ex}\n"
-      if ex.backtrace
-        Logster.add_to_env(fake_env, :backtrace, ex.backtrace)
-      end
-
-      Logster.add_to_env(fake_env, :current_hostname, Discourse.current_hostname)
-
-      Thread.current[Logster::Logger::LOGSTER_ENV] = fake_env
-      Logster.logger.error(text)
-    rescue => e
-      Logster.logger.fatal("Failed to log exception #{ex} #{hash}\nReason: #{e.class} #{e}\n#{e.backtrace.join("\n")}")
-    ensure
-      Thread.current[Logster::Logger::LOGSTER_ENV] = nil
-    end
-  end
-
-  Sidekiq.error_handlers.clear
-  Sidekiq.error_handlers << SidekiqLogsterReporter.new
-
-  Sidekiq.strict_args!
 end