diff --git a/config/sidekiq_scheduler.yml b/config/sidekiq_scheduler.yml
index 04982453233..ccd8c479d26 100644
--- a/config/sidekiq_scheduler.yml
+++ b/config/sidekiq_scheduler.yml
@@ -256,6 +256,11 @@ VANotify::InProgressForms:
   class: VANotify::InProgressForms
   description: "In progress form reminder emails (sent via VaNotify)"
 
+VBADocuments::FlipperStatusAlert:
+  cron: '0 2,9,16 * * MON-FRI America/New_York'
+  class: VBADocuments::FlipperStatusAlert
+  description: "Checks status of Flipper features expected to be enabled and alerts to Slack if any are not enabled"
+
 VBADocuments::ReportMonthlySubmissions:
   cron: "4 3 2 1 * * America/New_York"
   class: VBADocuments::ReportMonthlySubmissions
diff --git a/modules/appeals_api/app/workers/appeals_api/flipper_status_alert.rb b/modules/appeals_api/app/workers/appeals_api/flipper_status_alert.rb
index 94c8d78227b..5ac16174b34 100644
--- a/modules/appeals_api/app/workers/appeals_api/flipper_status_alert.rb
+++ b/modules/appeals_api/app/workers/appeals_api/flipper_status_alert.rb
@@ -11,8 +11,7 @@ class FlipperStatusAlert
     DISABLED_FLAG_EMOJI = ':vertical_traffic_light:'
     MISSING_FLAG_EMOJI = ':no_entry_sign:'
 
-    # No need to retry since the schedule will run this every hour
-    sidekiq_options retry: false, unique_for: 30.minutes
+    sidekiq_options retry: 5, unique_for: 30.minutes
 
     def perform
       features_to_check = load_features_from_config
diff --git a/modules/vba_documents/app/services/vba_documents/slack/hash_notification.rb b/modules/vba_documents/app/services/vba_documents/slack/hash_notification.rb
new file mode 100644
index 00000000000..85d6fb33155
--- /dev/null
+++ b/modules/vba_documents/app/services/vba_documents/slack/hash_notification.rb
@@ -0,0 +1,34 @@
+# frozen_string_literal: true
+
+module VBADocuments
+  module Slack
+    class HashNotification
+      def initialize(params)
+        # Params are expected to be in the Sidekiq Job Format (https://github.com/mperham/sidekiq/wiki/Job-Format),
+        @params = params
+      end
+
+      def message_text
+        msg = "ENVIRONMENT: #{environment}".dup
+
+        params.each do |k, v|
+          msg << "\n#{k.to_s.upcase} : #{v}"
+        end
+
+        msg
+      end
+
+      private
+
+      attr_accessor :params
+
+      def environment
+        env = Settings.vsp_environment
+
+        env_emoji = Messenger::ENVIRONMENT_EMOJIS[env.to_sym]
+
+        ":#{env_emoji}: #{env} :#{env_emoji}:"
+      end
+    end
+  end
+end
diff --git a/modules/vba_documents/app/services/vba_documents/slack/messenger.rb b/modules/vba_documents/app/services/vba_documents/slack/messenger.rb
new file mode 100644
index 00000000000..f27455b665d
--- /dev/null
+++ b/modules/vba_documents/app/services/vba_documents/slack/messenger.rb
@@ -0,0 +1,37 @@
+# frozen_string_literal: true
+
+require 'common/client/base'
+
+module VBADocuments
+  module Slack
+    class Messenger
+      ALERT_URL = Settings.vba_documents.slack.default_alert_url
+      ENVIRONMENT_EMOJIS = { production: 'rotating_light', sandbox: 'rocket', staging: 'construction',
+                             development: 'brain' }.freeze
+
+      def initialize(params)
+        @params = params
+      end
+
+      def notify!
+        Faraday.post(ALERT_URL, request_body, request_headers)
+      end
+
+      private
+
+      attr_reader :params
+
+      def notification
+        VBADocuments::Slack::HashNotification.new(params)
+      end
+
+      def request_body
+        { text: notification.message_text }.to_json
+      end
+
+      def request_headers
+        { 'Content-type' => 'application/json; charset=utf-8' }
+      end
+    end
+  end
+end
diff --git a/modules/vba_documents/app/workers/vba_documents/flipper_status_alert.rb b/modules/vba_documents/app/workers/vba_documents/flipper_status_alert.rb
new file mode 100644
index 00000000000..8f0eb9a6692
--- /dev/null
+++ b/modules/vba_documents/app/workers/vba_documents/flipper_status_alert.rb
@@ -0,0 +1,85 @@
+# frozen_string_literal: true
+
+require 'sidekiq'
+require 'flipper/utilities/bulk_feature_checker'
+
+module VBADocuments
+  class FlipperStatusAlert
+    include Sidekiq::Worker
+
+    WARNING_EMOJI = ':warning:'
+    DISABLED_FLAG_EMOJI = ':vertical_traffic_light:'
+    MISSING_FLAG_EMOJI = ':no_entry_sign:'
+
+    sidekiq_options retry: 5, unique_for: 30.minutes
+
+    def perform
+      features_to_check = load_features_from_config
+      if features_to_check.present?
+        @feature_statuses = Flipper::Utilities::BulkFeatureChecker.enabled_status(features_to_check)
+
+        slack_notify unless all_features_enabled?
+      end
+    end
+
+    private
+
+    def load_features_from_config
+      file_path = VBADocuments::Engine.root.join('config', 'flipper', 'enabled_features.yml')
+      feature_hash = read_config_file(file_path)
+      return [] if feature_hash.nil?
+
+      env_hash = feature_hash.fetch(Settings.vsp_environment.to_s, []) || []
+      features = (env_hash + (feature_hash['common'] || [])).uniq.sort
+
+      if features.empty?
+        VBADocuments::Slack::Messenger.new(
+          {
+            warning: "#{WARNING_EMOJI} #{self.class.name} has no configured enabled features",
+            file_path: file_path.to_s
+          }
+        ).notify!
+      end
+
+      features
+    end
+
+    def read_config_file(path)
+      if File.exist?(path)
+        YAML.load_file(path) || {}
+      else
+        VBADocuments::Slack::Messenger.new(
+          {
+            warning: "#{WARNING_EMOJI} #{self.class.name} features file does not exist",
+            file_path: path.to_s
+          }
+        ).notify!
+        nil
+      end
+    end
+
+    def all_features_enabled?
+      @feature_statuses[:missing].empty? && @feature_statuses[:disabled].empty?
+    end
+
+    def slack_notify
+      slack_details = {
+        class: self.class.name,
+        warning: "#{WARNING_EMOJI} One or more features expected to be enabled were found disabled or missing",
+        disabled_flags: slack_message(:disabled),
+        missing_flags: slack_message(:missing)
+      }
+
+      VBADocuments::Slack::Messenger.new(slack_details).notify!
+    end
+
+    def slack_message(flag_category)
+      if @feature_statuses[flag_category].present?
+        emoji = self.class.const_get("#{flag_category.upcase}_FLAG_EMOJI")
+        "#{emoji} #{@feature_statuses[flag_category].join(', ')} #{emoji}"
+      else
+        'None'
+      end
+    end
+  end
+end
diff --git a/modules/vba_documents/config/flipper/enabled_features.yml b/modules/vba_documents/config/flipper/enabled_features.yml
new file mode 100644
index 00000000000..20ea1052b38
--- /dev/null
+++ b/modules/vba_documents/config/flipper/enabled_features.yml
@@ -0,0 +1,6 @@
+common:
+  - test_feature_flag_alert_temp
+development:
+staging:
+sandbox:
+production:
diff --git a/modules/vba_documents/spec/services/vba_documents/slack/hash_notification_spec.rb b/modules/vba_documents/spec/services/vba_documents/slack/hash_notification_spec.rb
new file mode 100644
index 00000000000..44164f92a35
--- /dev/null
+++ b/modules/vba_documents/spec/services/vba_documents/slack/hash_notification_spec.rb
@@ -0,0 +1,34 @@
+# frozen_string_literal: true
+
+require 'rails_helper'
+
+describe VBADocuments::Slack::HashNotification do
+  describe '#message_text' do
+    let(:params) do
+      {
+        'test_key' => 'test_value',
+        'args' => %w[1234 5678],
+        'gibberish' => 2,
+        'indeed' => 'indeed gibberish',
+        'message' => 'Something happened here'
+      }
+    end
+
+    it 'returns the VSP environment' do
+      with_settings(Settings, vsp_environment: 'staging') do
+        expect(
+          described_class.new(params).message_text
+        ).to include('ENVIRONMENT: :construction: staging :construction:')
+      end
+    end
+
+    it 'displays all the keys capitalized and formatted' do
+      with_settings(Settings, vsp_environment: 'staging') do
+        expect(described_class.new(params).message_text).to include(
+          "\nTEST_KEY : test_value\nARGS : [\"1234\", \"5678\"]
+GIBBERISH : 2\nINDEED : indeed gibberish\nMESSAGE : Something happened here"
+        )
+      end
+    end
+  end
+end
diff --git a/modules/vba_documents/spec/services/vba_documents/slack/messenger_spec.rb b/modules/vba_documents/spec/services/vba_documents/slack/messenger_spec.rb
new file mode 100644
index 00000000000..dcbd7827a2e
--- /dev/null
+++ b/modules/vba_documents/spec/services/vba_documents/slack/messenger_spec.rb
@@ -0,0 +1,34 @@
+# frozen_string_literal: true
+
+require 'rails_helper'
+
+describe VBADocuments::Slack::Messenger do
+  describe '.notify!' do
+    let(:params) do
+      {
+        'class' => 'SomeClass',
+        'args' => %w[1234 5678],
+        'retry_count' => 2,
+        'error_class' => 'RuntimeError',
+        'error_message' => 'Here there be dragons',
+        'failed_at' => 1_613_670_737.966083,
+        'retried_at' => 1_613_680_062.5507782
+      }
+    end
+
+    it 'sends a network request' do
+      with_settings(Settings, vsp_environment: 'production') do
+        with_settings(Settings.vba_documents.slack, default_alert_url: 'default alert url') do
+          body = { text: VBADocuments::Slack::HashNotification.new(params).message_text }.to_json
+          headers = { 'Content-type' => 'application/json; charset=utf-8' }
+
+          allow(Faraday).to receive(:post).with(VBADocuments::Slack::Messenger::ALERT_URL, body, headers)
+
+          VBADocuments::Slack::Messenger.new(params).notify!
+
+          expect(Faraday).to have_received(:post).with(VBADocuments::Slack::Messenger::ALERT_URL, body, headers)
+        end
+      end
+    end
+  end
+end
diff --git a/modules/vba_documents/spec/workers/flipper_status_alert_spec.rb b/modules/vba_documents/spec/workers/flipper_status_alert_spec.rb
new file mode 100644
index 00000000000..74841e71580
--- /dev/null
+++ b/modules/vba_documents/spec/workers/flipper_status_alert_spec.rb
@@ -0,0 +1,146 @@
+# frozen_string_literal: true
+
+require 'rails_helper'
+require 'flipper/utilities/bulk_feature_checker'
+
+describe VBADocuments::FlipperStatusAlert, type: :job do
+  include FixtureHelpers
+
+  before { Sidekiq::Worker.clear_all }
+
+  describe '#perform' do
+    let(:messenger_instance) { instance_double(VBADocuments::Slack::Messenger) }
+    let(:config_file_path) { VBADocuments::Engine.root.join('config', 'flipper', 'enabled_features.yml') }
+
+    let(:warning_emoji) { described_class::WARNING_EMOJI }
+    let(:disabled_flag_emoji) { described_class::DISABLED_FLAG_EMOJI }
+    let(:missing_flag_emoji) { described_class::MISSING_FLAG_EMOJI }
+
+    let(:missing_file_message) { "#{warning_emoji} #{described_class} features file does not exist" }
+    let(:no_features_message) { "#{warning_emoji} #{described_class} has no configured enabled features" }
+    let(:flag_status_message) do
+      "#{warning_emoji} One or more features expected to be enabled were found disabled or missing"
+    end
+
+    it 'notifies Slack of missing config file when no config file found' do
+      allow(File).to receive(:exist?).and_return(false)
+      expected_notify = { warning: missing_file_message, file_path: config_file_path.to_s }
+      expect(VBADocuments::Slack::Messenger).to receive(:new).with(expected_notify).and_return(messenger_instance)
+      expect(messenger_instance).to receive(:notify!).once
+
+      described_class.new.perform
+    end
+
+    it 'notifies Slack that no features were found when config file contains no features' do
+      allow(YAML).to receive(:load_file).and_return({ 'common' => nil, 'production' => nil })
+      expected_notify = { warning: no_features_message, file_path: config_file_path.to_s }
+      expect(VBADocuments::Slack::Messenger).to receive(:new).with(expected_notify).and_return(messenger_instance)
+      expect(messenger_instance).to receive(:notify!).once
+
+      with_settings(Settings, vsp_environment: 'production') do
+        described_class.new.perform
+      end
+    end
+
+    it 'notifies Slack that no features were found when config file is empty (no keys)' do
+      allow(YAML).to receive(:load_file).and_return(nil)
+      expected_notify = { warning: no_features_message, file_path: config_file_path.to_s }
+      expect(VBADocuments::Slack::Messenger).to receive(:new).with(expected_notify).and_return(messenger_instance)
+      expect(messenger_instance).to receive(:notify!).once
+
+      described_class.new.perform
+    end
+
+    it 'fetches enabled status of common and current env features when config file contains both' do
+      allow(YAML).to receive(:load_file).and_return({ 'common' => %w[feature1], 'production' => %w[feature2] })
+      bulk_checker_result = { enabled: [], disabled: [], missing: %w[feature1 feature2] }
+      expect(Flipper::Utilities::BulkFeatureChecker)
+        .to receive(:enabled_status).with(%w[feature1 feature2]).and_return(bulk_checker_result)
+      allow(VBADocuments::Slack::Messenger).to receive(:new).and_return(messenger_instance)
+      allow(messenger_instance).to receive(:notify!)
+
+      with_settings(Settings, vsp_environment: 'production') do
+        described_class.new.perform
+      end
+    end
+
+    it 'fetches enabled status of common features only when config file contains no current env features' do
+      allow(YAML).to receive(:load_file).and_return({ 'common' => %w[feature1], 'development' => nil })
+      bulk_checker_result = { enabled: [], disabled: [], missing: %w[feature1] }
+      expect(Flipper::Utilities::BulkFeatureChecker)
+        .to receive(:enabled_status).with(%w[feature1]).and_return(bulk_checker_result)
+      allow(VBADocuments::Slack::Messenger).to receive(:new).and_return(messenger_instance)
+      allow(messenger_instance).to receive(:notify!)
+
+      with_settings(Settings, vsp_environment: 'development') do
+        described_class.new.perform
+      end
+    end
+
+    it 'fetches enabled status of current env features only when config file contains no common features' do
+      allow(YAML).to receive(:load_file).and_return({ 'common' => nil, 'staging' => %w[feature1] })
+      bulk_checker_result = { enabled: [], disabled: [], missing: %w[feature1] }
+      expect(Flipper::Utilities::BulkFeatureChecker)
+        .to receive(:enabled_status).with(%w[feature1]).and_return(bulk_checker_result)
+      allow(VBADocuments::Slack::Messenger).to receive(:new).and_return(messenger_instance)
+      allow(messenger_instance).to receive(:notify!)
+
+      with_settings(Settings, vsp_environment: 'staging') do
+        described_class.new.perform
+      end
+    end
+
+    it 'does not notify Slack when all features are enabled' do
+      bulk_checker_result = { enabled: %w[feature1 feature2], disabled: [], missing: [] }
+      allow(Flipper::Utilities::BulkFeatureChecker).to receive(:enabled_status).and_return(bulk_checker_result)
+      expect(VBADocuments::Slack::Messenger).not_to receive(:new)
+
+      described_class.new.perform
+    end
+
+    it 'notifies Slack when some features are disabled' do
+      bulk_checker_result = { enabled: %w[feature1], disabled: %w[feature2 feature3], missing: [] }
+      allow(Flipper::Utilities::BulkFeatureChecker).to receive(:enabled_status).and_return(bulk_checker_result)
+      expected_notify = {
+        class: described_class.name,
+        warning: flag_status_message,
+        disabled_flags: "#{disabled_flag_emoji} feature2, feature3 #{disabled_flag_emoji}",
+        missing_flags: 'None'
+      }
+      expect(VBADocuments::Slack::Messenger).to receive(:new).with(expected_notify).and_return(messenger_instance)
+      expect(messenger_instance).to receive(:notify!).once
+
+      described_class.new.perform
+    end
+
+    it 'notifies Slack when some features are missing' do
+      bulk_checker_result = { enabled: %w[feature1], disabled: [], missing: %w[feature2 feature3] }
+      allow(Flipper::Utilities::BulkFeatureChecker).to receive(:enabled_status).and_return(bulk_checker_result)
+      expected_notify = {
+        class: described_class.name,
+        warning: flag_status_message,
+        disabled_flags: 'None',
+        missing_flags: "#{missing_flag_emoji} feature2, feature3 #{missing_flag_emoji}"
+      }
+      expect(VBADocuments::Slack::Messenger).to receive(:new).with(expected_notify).and_return(messenger_instance)
+      expect(messenger_instance).to receive(:notify!).once
+
+      described_class.new.perform
+    end
+
+    it 'notifies slack when there are disabled and missing features' do
+      bulk_checker_result = { enabled: %w[feature1], disabled: %w[feature2 feature3], missing: %w[feature4 feature5] }
+      allow(Flipper::Utilities::BulkFeatureChecker).to receive(:enabled_status).and_return(bulk_checker_result)
+      expected_notify = {
+        class: described_class.name,
+        warning: flag_status_message,
+        disabled_flags: "#{disabled_flag_emoji} feature2, feature3 #{disabled_flag_emoji}",
+        missing_flags: "#{missing_flag_emoji} feature4, feature5 #{missing_flag_emoji}"
+      }
+      expect(VBADocuments::Slack::Messenger).to receive(:new).with(expected_notify).and_return(messenger_instance)
+      expect(messenger_instance).to receive(:notify!).once
+
+      described_class.new.perform
+    end
+  end
+end