diff --git a/plugins/automation/app/jobs/regular/discourse_automation/send_flag_email.rb b/plugins/automation/app/jobs/regular/discourse_automation/send_flag_email.rb
new file mode 100644
index 00000000000..fcf8ce3fdf5
--- /dev/null
+++ b/plugins/automation/app/jobs/regular/discourse_automation/send_flag_email.rb
@@ -0,0 +1,65 @@
+# frozen_string_literal: true
+
+module Jobs
+  module DiscourseAutomation
+    class SendFlagEmail < ::Jobs::Base
+      def execute(args)
+        post_action = PostAction.find_by(id: args[:post_action_id])
+        return if post_action.blank?
+
+        post = post_action&.post
+        return if post.blank?
+
+        email = args[:email]
+        raise Discourse::InvalidParameters.new(:email) if email.blank?
+
+        email_template =
+          ::DiscourseAutomation::Field.where(id: args[:email_template_automation_field_id]).pick(
+            :metadata,
+          )[
+            "value"
+          ]
+
+        if email_template.blank?
+          raise Discourse::InvalidParameters.new(:email_template_automation_field_id)
+        end
+
+        placeholders = build_placeholders(post_action, post)
+
+        subject =
+          I18n.t(
+            "discourse_automation.scriptables.email_on_flagged_post.subject",
+            topic_title: placeholders[:topic_title],
+            flagger_username: placeholders[:flagger_username],
+          )
+
+        body =
+          ::DiscourseAutomation::Scriptable::Utils.apply_placeholders(email_template, placeholders)
+
+        ::DiscourseAutomation::FlagMailer.send_flag_email(email, subject:, body:).deliver_now
+      end
+
+      private
+
+      def build_placeholders(post_action, post)
+        topic = post.topic
+        flagger = post_action.user
+        target_user = post.user
+
+        {
+          topic_url: topic.url,
+          post_url: post.full_url,
+          topic_title: topic&.title,
+          post_number: post.post_number,
+          flagger_username: flagger.username,
+          flagged_username: target_user.username,
+          flag_type: PostActionTypeView.new.names[post_action.post_action_type_id],
+          category: topic.category&.name,
+          tags: topic.tags&.map(&:name)&.join(", "),
+          site_title: SiteSetting.title,
+          post_excerpt: post.excerpt_for_topic,
+        }.compact
+      end
+    end
+  end
+end
diff --git a/plugins/automation/app/mailers/discourse_automation/flag_mailer.rb b/plugins/automation/app/mailers/discourse_automation/flag_mailer.rb
new file mode 100644
index 00000000000..5eb569b955c
--- /dev/null
+++ b/plugins/automation/app/mailers/discourse_automation/flag_mailer.rb
@@ -0,0 +1,17 @@
+# frozen_string_literal: true
+
+module DiscourseAutomation
+  class FlagMailer < ActionMailer::Base
+    include Email::BuildEmailHelper
+
+    def send_flag_email(to_address, subject:, body:)
+      build_email(
+        to_address,
+        subject: subject,
+        body: body,
+        add_unsubscribe_link: false,
+        allow_reply_by_email: false,
+      )
+    end
+  end
+end
diff --git a/plugins/automation/app/models/discourse_automation/automation.rb b/plugins/automation/app/models/discourse_automation/automation.rb
index a70a389c01a..d84889dc107 100644
--- a/plugins/automation/app/models/discourse_automation/automation.rb
+++ b/plugins/automation/app/models/discourse_automation/automation.rb
@@ -100,6 +100,7 @@ module DiscourseAutomation
     def upsert_field!(name, component, metadata, target: "script")
       field = fields.find_or_initialize_by(name: name, component: component, target: target)
       field.update!(metadata: metadata)
+      field
     end
 
     def self.deserialize_context(context)
diff --git a/plugins/automation/config/locales/client.en.yml b/plugins/automation/config/locales/client.en.yml
index ec9320b058a..f0ba17e52bb 100644
--- a/plugins/automation/config/locales/client.en.yml
+++ b/plugins/automation/config/locales/client.en.yml
@@ -61,6 +61,14 @@ en:
         text:
           label: Text
       triggerables:
+        post_flag_created:
+          fields:
+            categories:
+              label: Categories
+              description: Only trigger when the flagged topic is in these categories
+            tags:
+              label: Tags
+              description: Only trigger when the flagged topic has any of these tags
         not_found: Couldn’t find trigger `%{trigger}` for automation `%{automation}`, ensure the associated plugin is installed
         user_badge_granted:
           fields:
@@ -271,6 +279,14 @@ en:
               label: Tags
               description: Optional, will trigger only if the post has any of these tags
       scriptables:
+        email_on_flagged_post:
+          fields:
+            email_template:
+              label: Email template
+              description: Supports automation placeholders
+            recipients:
+              label: Recipients
+              description: Users or email addresses to notify
         not_found: Couldn’t find script `%{script}` for automation `%{automation}`, ensure the associated plugin is installed
         zapier_webhook:
           fields:
diff --git a/plugins/automation/config/locales/server.en.yml b/plugins/automation/config/locales/server.en.yml
index 9bbac53a215..6520eeed6a9 100644
--- a/plugins/automation/config/locales/server.en.yml
+++ b/plugins/automation/config/locales/server.en.yml
@@ -16,6 +16,9 @@ en:
         invalid_field: Field’s component `%{component}` is not usable on `%{target}:%{target_name}`.
         invalid_metadata: Data for `%{field}` is invalid or component `%{component}` is unknown.
     triggerables:
+      post_flag_created:
+        title: Post flag created
+        description: Triggers an automation when a post is flagged
       errors:
         custom_fields_or_user_profile_required: "At least one of 'custom_fields' or 'user_profile' must be provided."
       user_badge_granted:
@@ -74,6 +77,24 @@ en:
         title: After user update
         description: When a user updates any information the automation will be triggered
     scriptables:
+      email_on_flagged_post:
+        title: Email on flagged post
+        description: Send a custom email whenever a flag is created on a post
+        subject: "Flagged post: %{topic_title} (%{flagger_username})"
+        default_template: |-
+          A post has been flagged.
+
+          Topic: {{topic_title}} ({{topic_url}})
+          Post: {{post_url}} (#{{post_number}})
+          Flag type: {{flag_type}}
+          Flagged user: {{flagged_username}}
+          Flagged by: {{flagger_username}}
+          Category: {{category}}
+          Tags: {{tags}}
+
+          --------
+          Post excerpt:
+          {{post_excerpt}}
       post:
         title: Create a post
         description: Create a post on a specified topic
diff --git a/plugins/automation/lib/discourse_automation/event_handlers.rb b/plugins/automation/lib/discourse_automation/event_handlers.rb
index ba9630ec666..893f2526df0 100644
--- a/plugins/automation/lib/discourse_automation/event_handlers.rb
+++ b/plugins/automation/lib/discourse_automation/event_handlers.rb
@@ -430,5 +430,31 @@ module DiscourseAutomation
             .destroy_all
         end
     end
+
+    def self.handle_post_flag_created(post_action)
+      name = DiscourseAutomation::Triggers::POST_FLAG_CREATED
+
+      post = post_action.post
+      topic = post.topic
+
+      DiscourseAutomation::Automation
+        .where(trigger: name, enabled: true)
+        .find_each do |automation|
+          flag_type_field = automation.trigger_field("flag_type")
+          flag_type_id = flag_type_field["value"]
+
+          next if flag_type_id.present? && flag_type_id != post_action.post_action_type_id
+
+          categories = automation.trigger_field("categories")["value"]
+          next if categories.present? && !categories.include?(topic.category_id)
+
+          if SiteSetting.tagging_enabled?
+            tags = automation.trigger_field("tags")["value"]
+            next if tags.present? && (topic.tags.map(&:name) & tags).empty?
+          end
+
+          automation.trigger!("kind" => name, "post_action_id" => post_action.id)
+        end
+    end
   end
 end
diff --git a/plugins/automation/lib/discourse_automation/scripts.rb b/plugins/automation/lib/discourse_automation/scripts.rb
index 20704f513bc..a3c0cd705be 100644
--- a/plugins/automation/lib/discourse_automation/scripts.rb
+++ b/plugins/automation/lib/discourse_automation/scripts.rb
@@ -9,6 +9,7 @@ module DiscourseAutomation
     AUTO_TAG_TOPIC = "auto_tag_topic"
     BANNER_TOPIC = "banner_topic"
     CLOSE_TOPIC = "close_topic"
+    EMAIL_ON_FLAGGED_POST = "email_on_flagged_post"
     FLAG_POST_ON_WORDS = "flag_post_on_words"
     GIFT_EXCHANGE = "gift_exchange"
     GROUP_CATEGORY_NOTIFICATION_DEFAULT = "group_category_notification_default"
diff --git a/plugins/automation/lib/discourse_automation/scripts/email_on_flagged_post.rb b/plugins/automation/lib/discourse_automation/scripts/email_on_flagged_post.rb
new file mode 100644
index 00000000000..44aaef2dc86
--- /dev/null
+++ b/plugins/automation/lib/discourse_automation/scripts/email_on_flagged_post.rb
@@ -0,0 +1,44 @@
+# frozen_string_literal: true
+
+DiscourseAutomation::Scriptable.add(DiscourseAutomation::Scripts::EMAIL_ON_FLAGGED_POST) do
+  version 1
+  run_in_background if !Rails.env.test?
+
+  triggerables [DiscourseAutomation::Triggers::POST_FLAG_CREATED]
+
+  field :email_template,
+        component: :message,
+        required: true,
+        accepts_placeholders: true,
+        default_value:
+          I18n.t("discourse_automation.scriptables.email_on_flagged_post.default_template")
+
+  field :recipients, component: :users, required: true
+
+  script do |context, fields, automation|
+    recipients = fields.dig("recipients", "value").uniq
+    next if recipients.blank?
+
+    to_emails = []
+    to_emails = to_emails.concat(recipients.select { |r| Email.is_valid?(r) })
+    to_users = recipients - to_emails
+
+    if to_users.present?
+      primary_emails = User.includes(:primary_email).filter_by_username(to_users).map(&:email)
+      to_emails.concat(primary_emails)
+    end
+
+    to_emails.uniq!
+
+    automation_email_template_field_id = automation.fields.where(name: "email_template").pick(:id)
+
+    to_emails.each do |email|
+      Jobs.enqueue(
+        Jobs::DiscourseAutomation::SendFlagEmail,
+        email:,
+        email_template_automation_field_id: automation_email_template_field_id,
+        post_action_id: context["post_action_id"],
+      )
+    end
+  end
+end
diff --git a/plugins/automation/lib/discourse_automation/triggers.rb b/plugins/automation/lib/discourse_automation/triggers.rb
index 08a3a7fbb67..4c3925de847 100644
--- a/plugins/automation/lib/discourse_automation/triggers.rb
+++ b/plugins/automation/lib/discourse_automation/triggers.rb
@@ -5,6 +5,7 @@ module DiscourseAutomation
     AFTER_POST_COOK = "after_post_cook"
     API_CALL = "api_call"
     CATEGORY_CREATED_EDITED = "category_created_edited"
+    POST_FLAG_CREATED = "post_flag_created"
     PM_CREATED = "pm_created"
     TOPIC_TAGS_CHANGED = "topic_tags_changed"
     POINT_IN_TIME = "point_in_time"
diff --git a/plugins/automation/lib/discourse_automation/triggers/post_flag_created.rb b/plugins/automation/lib/discourse_automation/triggers/post_flag_created.rb
new file mode 100644
index 00000000000..4d945294a62
--- /dev/null
+++ b/plugins/automation/lib/discourse_automation/triggers/post_flag_created.rb
@@ -0,0 +1,17 @@
+# frozen_string_literal: true
+
+DiscourseAutomation::Triggerable.add(DiscourseAutomation::Triggers::POST_FLAG_CREATED) do
+  field :categories, component: :categories
+  field :tags, component: :tags
+
+  placeholder :topic_url
+  placeholder :topic_title
+  placeholder :post_url
+  placeholder :post_number
+  placeholder :flagger_username
+  placeholder :flagged_username
+  placeholder :flag_type
+  placeholder :category
+  placeholder :tags
+  placeholder :post_excerpt
+end
diff --git a/plugins/automation/plugin.rb b/plugins/automation/plugin.rb
index 2046d3ba934..9cb09a1498e 100644
--- a/plugins/automation/plugin.rb
+++ b/plugins/automation/plugin.rb
@@ -52,6 +52,7 @@ after_initialize do
     lib/discourse_automation/scripts/banner_topic
     lib/discourse_automation/scripts/close_topic
     lib/discourse_automation/scripts/flag_post_on_words
+    lib/discourse_automation/scripts/email_on_flagged_post
     lib/discourse_automation/scripts/gift_exchange
     lib/discourse_automation/scripts/group_category_notification_default
     lib/discourse_automation/scripts/pin_topic
@@ -71,6 +72,7 @@ after_initialize do
     lib/discourse_automation/triggers/pm_created
     lib/discourse_automation/triggers/point_in_time
     lib/discourse_automation/triggers/post_created_edited
+    lib/discourse_automation/triggers/post_flag_created
     lib/discourse_automation/triggers/recurring
     lib/discourse_automation/triggers/stalled_topic
     lib/discourse_automation/triggers/stalled_wiki
@@ -206,6 +208,10 @@ after_initialize do
     DiscourseAutomation::EventHandlers.handle_post_created_edited(post, :edit)
   end
 
+  on(:flag_created) do |post_action|
+    DiscourseAutomation::EventHandlers.handle_post_flag_created(post_action) if post_action.post
+  end
+
   on(:category_created) do |category|
     DiscourseAutomation::EventHandlers.handle_category_created_edited(category, :create)
   end
diff --git a/plugins/automation/spec/jobs/regular/discourse_automation/send_flag_email_spec.rb b/plugins/automation/spec/jobs/regular/discourse_automation/send_flag_email_spec.rb
new file mode 100644
index 00000000000..a8a2a7c45ae
--- /dev/null
+++ b/plugins/automation/spec/jobs/regular/discourse_automation/send_flag_email_spec.rb
@@ -0,0 +1,92 @@
+# frozen_string_literal: true
+
+describe Jobs::DiscourseAutomation::SendFlagEmail do
+  fab!(:topic)
+  fab!(:post) { Fabricate(:post, topic:) }
+
+  fab!(:email_template_automation_field) do
+    field = nil
+
+    Fabricate(
+      :automation,
+      script: DiscourseAutomation::Scripts::EMAIL_ON_FLAGGED_POST,
+      trigger: DiscourseAutomation::Triggers::POST_FLAG_CREATED,
+    ).tap do |automation|
+      field =
+        automation.upsert_field!(
+          "email_template",
+          "message",
+          {
+            value:
+              I18n.t("discourse_automation.scriptables.email_on_flagged_post.default_template"),
+          },
+        )
+    end
+
+    field
+  end
+
+  fab!(:post_action) do
+    Fabricate(:post_action, post:, post_action_type_id: PostActionType.types[:spam])
+  end
+
+  describe "#execute" do
+    it "delivers email to the right recipient with the right subject and body" do
+      expect do
+        described_class.new.execute(
+          email: "recipient@example.com",
+          email_template_automation_field_id: email_template_automation_field.id,
+          post_action_id: post_action.id,
+        )
+      end.to change { ActionMailer::Base.deliveries.size }.by(1)
+
+      mail = ActionMailer::Base.deliveries.last
+
+      expect(mail.subject).to eq(
+        I18n.t(
+          "discourse_automation.scriptables.email_on_flagged_post.subject",
+          topic_title: topic.title,
+          flagger_username: post_action.user.username,
+        ),
+      )
+
+      expect(mail.body.to_s).to eq(<<~BODY.chomp)
+        A post has been flagged.
+
+        Topic: #{topic.title} (#{topic.url})
+        Post: #{post.full_url} (##{post.post_number})
+        Flag type: #{PostActionTypeView.new.names[post_action.post_action_type_id]}
+        Flagged user: #{post.user.username}
+        Flagged by: #{post_action.user.username}
+        Category: #{post.topic.category.name}
+        Tags: #{post.topic.tags.pluck(:name).join(", ")}
+
+        --------
+        Post excerpt:
+        #{post.excerpt_for_topic}
+      BODY
+    end
+
+    it "does not deliver email if `post_action_id` is invalid" do
+      expect do
+        described_class.new.execute(
+          email: "recipient@example.com",
+          email_template_automation_field_id: email_template_automation_field.id,
+          post_action_id: -999_999,
+        )
+      end.not_to change { ActionMailer::Base.deliveries.size }
+    end
+
+    it "does not deliver email if post associated with the post action has been destroyed" do
+      post_action.post.destroy!
+
+      expect do
+        described_class.new.execute(
+          email: "recipient@example.com",
+          email_template_automation_field_id: email_template_automation_field.id,
+          post_action_id: post_action.id,
+        )
+      end.not_to change { ActionMailer::Base.deliveries.size }
+    end
+  end
+end
diff --git a/plugins/automation/spec/scripts/email_on_flagged_post_spec.rb b/plugins/automation/spec/scripts/email_on_flagged_post_spec.rb
new file mode 100644
index 00000000000..434b92610ad
--- /dev/null
+++ b/plugins/automation/spec/scripts/email_on_flagged_post_spec.rb
@@ -0,0 +1,88 @@
+# frozen_string_literal: true
+
+describe "EmailOnFlaggedPost" do
+  fab!(:recipient) { Fabricate(:user, email: "recipient@example.com") }
+  fab!(:user_2, :user)
+  fab!(:flagger) { Fabricate(:user, trust_level: TrustLevel[2]) }
+  fab!(:second_flagger) { Fabricate(:user, trust_level: TrustLevel[2]) }
+  fab!(:topic)
+  fab!(:post) { Fabricate(:post, topic: topic) }
+
+  fab!(:automation) do
+    Fabricate(
+      :automation,
+      script: DiscourseAutomation::Scripts::EMAIL_ON_FLAGGED_POST,
+      trigger: DiscourseAutomation::Triggers::POST_FLAG_CREATED,
+    )
+  end
+
+  before do
+    SiteSetting.discourse_automation_enabled = true
+    SiteSetting.disable_emails = "no"
+  end
+
+  it "rejects email addresses that are invalid" do
+    automation.upsert_field!("recipients", "users", { value: ["@invalid-email"] })
+
+    expect do
+      result = PostActionCreator.spam(flagger, post)
+      expect(result.success).to eq(true)
+    end.not_to change { Jobs::DiscourseAutomation::SendFlagEmail.jobs.length }
+  end
+
+  it "rejects usernames that do not exist" do
+    automation.upsert_field!("recipients", "users", { value: ["nonexistent_user"] })
+
+    expect do
+      result = PostActionCreator.spam(flagger, post)
+      expect(result.success).to eq(true)
+    end.not_to change { Jobs::DiscourseAutomation::SendFlagEmail.jobs.length }
+  end
+
+  it "deduplicates email addresses" do
+    automation.upsert_field!("recipients", "users", { value: [recipient.email, recipient.email] })
+
+    expect do
+      result = PostActionCreator.spam(flagger, post)
+      expect(result.success).to eq(true)
+    end.to change { Jobs::DiscourseAutomation::SendFlagEmail.jobs.length }.by(1)
+  end
+
+  it "enqueues a job per recipient with placeholders applied" do
+    automation.upsert_field!("recipients", "users", { value: [recipient.email, user_2.username] })
+
+    field =
+      automation.upsert_field!(
+        "email_template",
+        "message",
+        {
+          value: I18n.t("discourse_automation.scriptables.email_on_flagged_post.default_template"),
+        },
+      )
+
+    result = nil
+
+    expect do
+      result = PostActionCreator.spam(flagger, post)
+      expect(result.success).to eq(true)
+    end.to change { Jobs::DiscourseAutomation::SendFlagEmail.jobs.length }.by(2)
+
+    expect_job_enqueued(
+      job: Jobs::DiscourseAutomation::SendFlagEmail,
+      args: {
+        email: recipient.email,
+        email_template_automation_field_id: field.id,
+        post_action_id: result.post_action.id,
+      },
+    )
+
+    expect_job_enqueued(
+      job: Jobs::DiscourseAutomation::SendFlagEmail,
+      args: {
+        email: user_2.primary_email.email,
+        email_template_automation_field_id: field.id,
+        post_action_id: result.post_action.id,
+      },
+    )
+  end
+end
diff --git a/plugins/automation/spec/triggers/post_flag_created_spec.rb b/plugins/automation/spec/triggers/post_flag_created_spec.rb
new file mode 100644
index 00000000000..a457ee6a5b5
--- /dev/null
+++ b/plugins/automation/spec/triggers/post_flag_created_spec.rb
@@ -0,0 +1,82 @@
+# frozen_string_literal: true
+
+describe DiscourseAutomation::Triggers::POST_FLAG_CREATED do
+  fab!(:flagger) { Fabricate(:user, trust_level: TrustLevel[2]) }
+  fab!(:second_flagger) { Fabricate(:user, trust_level: TrustLevel[2]) }
+  fab!(:category)
+  fab!(:tag)
+  fab!(:topic) { Fabricate(:topic, category: category, tags: [tag]) }
+  fab!(:post) { Fabricate(:post, topic: topic) }
+
+  fab!(:automation) do
+    Fabricate(:automation, trigger: DiscourseAutomation::Triggers::POST_FLAG_CREATED)
+  end
+
+  before { SiteSetting.discourse_automation_enabled = true }
+
+  it "ignores the tags field if tagging is disabled" do
+    SiteSetting.tagging_enabled = false
+
+    automation.upsert_field!("tags", "tags", { value: [tag.name] }, target: "trigger")
+
+    expect do
+      result = PostActionCreator.spam(flagger, Fabricate(:post, topic: Fabricate(:topic)))
+      expect(result.success).to eq(true)
+    end.to change { automation.reload.stats.count }.by(1)
+  end
+
+  it "only triggers the automation if flagged post is in a topic with the specified tags defined by the tags field" do
+    automation.upsert_field!("tags", "tags", { value: [tag.name] }, target: "trigger")
+
+    post_action_id = nil
+
+    triggered_automations =
+      capture_contexts do
+        expect do
+          result = PostActionCreator.spam(flagger, post)
+          expect(result.success).to eq(true)
+          post_action_id = result.post_action.id
+
+          result = PostActionCreator.spam(flagger, Fabricate(:post, topic: Fabricate(:topic)))
+          expect(result.success).to eq(true)
+        end.to change { automation.reload.stats.count }.by(1)
+      end
+
+    expect(triggered_automations.length).to eq(1)
+
+    triggered_automation = triggered_automations.first
+
+    expect(triggered_automation["kind"]).to eq(DiscourseAutomation::Triggers::POST_FLAG_CREATED)
+    expect(triggered_automation["post_action_id"]).to eq(post_action_id)
+  end
+
+  it "only triggers the automation if flagged post is in a topic with the specified categories defined by the categories field" do
+    automation.upsert_field!(
+      "categories",
+      "categories",
+      { value: [category.id] },
+      target: "trigger",
+    )
+
+    post_action_id = nil
+
+    triggered_automations =
+      capture_contexts do
+        expect do
+          result = PostActionCreator.spam(flagger, post)
+          expect(result.success).to eq(true)
+          post_action_id = result.post_action.id
+
+          result = PostActionCreator.spam(flagger, Fabricate(:post, topic: Fabricate(:topic)))
+          expect(result.success).to eq(true)
+        end.to change { automation.reload.stats.count }.by(1)
+      end
+
+    expect(triggered_automations.length).to eq(1)
+
+    triggered_automation = triggered_automations.first
+
+    expect(triggered_automation["kind"]).to eq(DiscourseAutomation::Triggers::POST_FLAG_CREATED)
+    expect(triggered_automation["post_action_id"]).to eq(post_action_id)
+  end
+end
diff --git a/script/i18n_lint.rb b/script/i18n_lint.rb
index 2e089622f33..98212682f26 100755
--- a/script/i18n_lint.rb
+++ b/script/i18n_lint.rb
@@ -56,8 +56,9 @@ class LocaleFileValidator
   PLURALIZATION_KEYS = %w[zero one two few many other]
   ENGLISH_KEYS = %w[one other]
 
-  EXEMPTED_DOUBLE_CURLY_BRACKET_KEYS = [
-    "js.discourse_automation.scriptables.auto_responder.fields.word_answer_list.description",
+  EXEMPTED_DOUBLE_CURLY_BRACKET_KEYS = %w[
+    js.discourse_automation.scriptables.auto_responder.fields.word_answer_list.description
+    discourse_automation.scriptables.email_on_flagged_post.default_template
   ]
 
   def initialize(filename)