diff --git a/.gitlab-ci.yml b/.gitlab-ci.yml
index 0e36154b270..a3d07207b4a 100644
--- a/.gitlab-ci.yml
+++ b/.gitlab-ci.yml
@@ -67,9 +67,7 @@ stages:
 
 workflow:
   rules:
-    - if: '$CI_PIPELINE_SOURCE == "schedule"'
-      when: never
-    - if: '$CI_PIPELINE_SOURCE == "merge_request_event" || $CI_PIPELINE_SOURCE == "external_pull_request_event"'
+    - if: '$CI_PIPELINE_SOURCE == "merge_request_event" || $CI_PIPELINE_SOURCE == "external_pull_request_event" || $CI_PIPELINE_SOURCE == "schedule"'
     - if: '$CI_PIPELINE_SOURCE == "merge_request_event" || $CI_PIPELINE_SOURCE == "external_pull_request_event" || $CI_PIPELINE_SOURCE == "web"'
     - if: '$CI_COMMIT_BRANCH == "main" || $CI_COMMIT_BRANCH == "stages/prod"'
     - if: '$CI_MERGE_REQUEST_IID || $CI_EXTERNAL_PULL_REQUEST_IID'
@@ -341,6 +339,7 @@ js_tests:
     - *yarn_install
     - yarn test
 
+# Can be removed once pinpoint_check_scheduled is confirmed
 pinpoint-check:
   needs:
     - job: install
@@ -353,6 +352,7 @@ pinpoint-check:
     - *yarn_install
     - make lint_country_dialing_codes
 
+# Can be removed once audit_packages_scheduled is confirmed
 audit_packages:
   needs:
     - job: install
@@ -838,3 +838,51 @@ ecr-scan-ci:
   stage: scan
   variables:
     ecr_repo: idp/ci
+
+pinpoint_check_scheduled:
+  needs:
+    - job: install
+  cache:
+    - <<: *ruby_cache
+    - <<: *yarn_cache
+  script:
+    - *bundle_install
+    - *yarn_install
+    - make lint_country_dialing_codes
+  after_script:
+    - |-
+      if [ "$CI_JOB_STATUS" != "success" ]; then
+        ./scripts/notify-slack \
+          --icon ":gitlab:"  \
+          --username "gitlab-notify" \
+          --channel "#login-appdev" \
+          --webhook "${SLACK_WEBHOOK}" \
+          --raise \
+          --text "Pinpoint supported countries check in GitLab failed.\nBuild Results: ${CI_JOB_URL}.\nCheck results locally with 'make lint_country_dialing_codes'"
+      fi
+  rules:
+    - if: $CI_PIPELINE_SOURCE == "schedule"
+
+audit_packages_scheduled:
+  needs:
+    - job: install
+  cache:
+    - <<: *ruby_cache
+    - <<: *yarn_cache
+  script:
+    - *bundle_install
+    - *yarn_install
+    - make audit
+  after_script:
+    - |-
+      if [ "$CI_JOB_STATUS" != "success" ]; then
+        ./scripts/notify-slack \
+          --icon ":gitlab:"  \
+          --username "gitlab-notify" \
+          --channel "#login-appdev" \
+          --webhook "${SLACK_WEBHOOK}" \
+          --raise \
+          --text "Dependencies audit in GitLab failed.\nBuild Results: ${CI_JOB_URL}\nCheck results locally with 'make audit'"
+      fi
+  rules:
+    - if: $CI_PIPELINE_SOURCE == "schedule"
diff --git a/scripts/notify-slack b/scripts/notify-slack
new file mode 100755
index 00000000000..52066f45598
--- /dev/null
+++ b/scripts/notify-slack
@@ -0,0 +1,144 @@
+#!/usr/bin/env ruby
+# frozen_string_literal: true
+
+require 'json'
+require 'net/http'
+require 'optparse'
+
+# Posts a message to Slack via webhook
+class NotifySlack
+  def run(argv:, stdin:, stdout:)
+    channel = nil
+    username = nil
+    text = nil
+    webhook = nil
+    icon = ':login-gov:'
+    raise_on_failure = false
+
+    program_name = File.basename($PROGRAM_NAME)
+
+    parser = OptionParser.new do |opts|
+      opts.banner = <<~STR
+        #{program_name} [options]
+
+        Usage:
+
+        * Using arguments
+
+          #{program_name} --text "my *message*" \\
+           --channel "#some-channel" \\
+           --webhook https://example.com/webhook
+
+        * Passing text over STDIN
+
+          echo "my *message*" | #{program_name} --text - \\
+            --channel "#some-channel" \\
+            --webhook https://example.com/webhook
+
+        Options:
+      STR
+
+      opts.on('--channel CHANNEL', 'which channel to notify') do |channel_v|
+        channel = channel_v
+      end
+
+      opts.on('--webhook WEBHOOK', 'Slack webhook URL') do |webhook_v|
+        webhook = webhook_v
+      end
+
+      opts.on('--username USERNAME', 'which username to notify as') do |username_v|
+        username = username_v
+      end
+
+      opts.on('--text TEXT', 'text of notification, pass - to read from STDIN') do |text_v|
+        if text_v == '-'
+          if stdin.tty?
+            stdout.print 'please enter text of message: '
+            text = stdin.gets
+          else
+            text = stdin.read
+          end
+        else
+          text = text_v
+        end
+      end
+
+      opts.on('--icon ICON', 'slack emoji to use as icon (optional)') do |icon_v|
+        icon = icon_v
+      end
+
+      opts.on('--[no-]raise', <<~EOS) do |raise_v|
+        raise errors/exit uncleanly if the webhook fails. defaults to not raising
+      EOS
+        raise_on_failure = raise_v
+      end
+
+      opts.on('--help') do
+        puts opts
+        exit 0
+      end
+    end
+
+    parser.parse!(argv)
+
+    if !channel || !username || !text || !webhook
+      stdout.puts parser
+      exit 1
+    end
+
+    notify(
+      webhook: webhook,
+      channel: channel,
+      username: username,
+      text: text,
+      icon: format_icon(icon),
+    )
+    stdout.puts 'OK'
+  rescue Net::HTTPClientException => err
+    stdout.puts "#{program_name} HTTP ERROR: #{err.response.code}"
+    raise err if raise_on_failure
+  rescue => err
+    stdout.puts "#{program_name} ERROR: #{err.message}"
+    raise err if raise_on_failure
+  end
+
+  # @raise [Net::HTTPClientException] throws an error for non-successful response
+  # @return [Net::HTTPResponse]
+  def notify(webhook:, channel:, username:, text:, icon:)
+    url = URI(webhook)
+
+    req = Net::HTTP::Post.new(url)
+    req.form_data = {
+      'payload' => {
+        channel: channel,
+        username: username,
+        text: text,
+        icon_emoji: icon,
+      }.to_json,
+    }
+
+    Net::HTTP.start(
+      url.hostname,
+      url.port,
+      use_ssl: url.scheme == 'https',
+      open_timeout: 1,
+      read_timeout: 1,
+      write_timeout: 1,
+      ssl_timeout: 1,
+    ) do |http|
+      http.request(req)
+    end.value
+  end
+
+  def format_icon(icon)
+    if icon.start_with?(':') && icon.end_with?(':')
+      icon
+    else
+      ":#{icon}:"
+    end
+  end
+end
+
+if $PROGRAM_NAME == __FILE__
+  NotifySlack.new.run(argv: ARGV, stdin: STDIN, stdout: STDOUT)
+end
diff --git a/spec/scripts/notify-slack_spec.rb b/spec/scripts/notify-slack_spec.rb
new file mode 100644
index 00000000000..6ddf1903e4a
--- /dev/null
+++ b/spec/scripts/notify-slack_spec.rb
@@ -0,0 +1,120 @@
+require 'spec_helper'
+require 'rack/utils'
+load File.expand_path('../../scripts/notify-slack', __dir__)
+
+RSpec.describe NotifySlack do
+  subject(:notifier) { described_class.new }
+
+  let(:webhook) { 'https://slack.example.com/abcdef/ghijkl' }
+  let(:channel) { '#fun-channel' }
+  let(:username) { 'notifier-bot' }
+  let(:text) { 'my message' }
+  let(:icon) { ':red_circle:' }
+
+  describe '#run' do
+    let(:argv) do
+      [
+        '--webhook',
+        webhook,
+        '--channel',
+        channel,
+        '--username',
+        username,
+        '--text',
+        text,
+        '--icon', icon
+      ]
+    end
+    let(:stdin) { StringIO.new }
+    let(:stdout) { StringIO.new }
+
+    subject(:run) do
+      notifier.run(argv:, stdin:, stdout:)
+    end
+
+    before do
+      allow(notifier).to receive(:exit)
+    end
+
+    context 'missing required argument' do
+      before do
+        argv.delete('--webhook')
+        argv.delete(webhook)
+      end
+
+      it 'prints help and exits uncleanly' do
+        expect(notifier).to receive(:exit).with(1)
+
+        run
+
+        expect(stdout.string).to include('Usage')
+      end
+    end
+
+    it 'notifies' do
+      post_request = stub_request(:post, webhook)
+
+      run
+
+      expect(post_request).to have_been_made
+    end
+
+    context 'network error' do
+      before do
+        stub_request(:post, webhook).to_return(status: 500)
+      end
+
+      it 'prints an error and exits cleanly' do
+        expect(notifier).to_not receive(:exit)
+
+        run
+
+        expect(stdout.string).to include('ERROR: 500')
+      end
+
+      context 'with --raise' do
+        before { argv << '--raise' }
+
+        it 'raises an error' do
+          expect { run }.to raise_error(Net::HTTPExceptions)
+        end
+      end
+    end
+  end
+
+  describe '#notify' do
+    subject(:notify) do
+      notifier.notify(webhook:, channel:, username:, text:, icon:)
+    end
+
+    it 'POSTs JSON inside of form encoding to the webhook' do
+      post_request = stub_request(:post, webhook).with(
+        headers: {
+          content_type: 'application/x-www-form-urlencoded',
+        },
+      ) do |req|
+        form = Rack::Utils.parse_query(req.body)
+        expect(JSON.parse(form['payload'], symbolize_names: true)).to eq(
+          channel:,
+          username:,
+          text:,
+          icon_emoji: icon,
+        )
+      end
+
+      notify
+
+      expect(post_request).to have_been_made
+    end
+  end
+
+  describe '#format_icon' do
+    it 'adds colons around icon names if missing' do
+      expect(notifier.format_icon('joy')).to eq(':joy:')
+    end
+
+    it 'leaves colons around icon names if present' do
+      expect(notifier.format_icon(':sob:')).to eq(':sob:')
+    end
+  end
+end