diff --git a/app/models/web_hook_event_type.rb b/app/models/web_hook_event_type.rb
index 818b4353bc8..7904472b2f3 100644
--- a/app/models/web_hook_event_type.rb
+++ b/app/models/web_hook_event_type.rb
@@ -16,6 +16,7 @@ class WebHookEventType < ActiveRecord::Base
   LIKE = 15
   USER_PROMOTED = 16
   TOPIC_VOTING = 17
+  CHAT_MESSAGE = 18
 
   has_and_belongs_to_many :web_hooks
 
@@ -34,6 +35,9 @@ class WebHookEventType < ActiveRecord::Base
     unless defined?(SiteSetting.voting_enabled) && SiteSetting.voting_enabled
       ids_to_exclude << TOPIC_VOTING
     end
+    unless defined?(SiteSetting.chat_enabled) && SiteSetting.chat_enabled
+      ids_to_exclude << CHAT_MESSAGE
+    end
 
     self.where.not(id: ids_to_exclude)
   end
diff --git a/db/fixtures/007_web_hook_event_types.rb b/db/fixtures/007_web_hook_event_types.rb
index 3bf745381c7..4ee43c57c7a 100644
--- a/db/fixtures/007_web_hook_event_types.rb
+++ b/db/fixtures/007_web_hook_event_types.rb
@@ -74,3 +74,8 @@ WebHookEventType.seed do |b|
   b.id = WebHookEventType::TOPIC_VOTING
   b.name = "topic_voting"
 end
+
+WebHookEventType.seed do |b|
+  b.id = WebHookEventType::CHAT_MESSAGE
+  b.name = "chat_message"
+end
diff --git a/plugins/chat/config/locales/client.en.yml b/plugins/chat/config/locales/client.en.yml
index 4b36fb9d635..6f5bfda6a09 100644
--- a/plugins/chat/config/locales/client.en.yml
+++ b/plugins/chat/config/locales/client.en.yml
@@ -19,6 +19,10 @@ en:
           descriptions:
             chat:
               create_message: "Create a chat message in a specified channel."
+      web_hooks:
+        chat_message_event:
+          name: "Chat message event"
+          details: "When a chat message is created, edited, trashed or restored."
     about:
       chat_messages_count: "Chat Messages"
       chat_channels_count: "Chat Channels"
diff --git a/plugins/chat/lib/chat/outgoing_web_hook_extension.rb b/plugins/chat/lib/chat/outgoing_web_hook_extension.rb
new file mode 100644
index 00000000000..41ee8f219aa
--- /dev/null
+++ b/plugins/chat/lib/chat/outgoing_web_hook_extension.rb
@@ -0,0 +1,13 @@
+# frozen_string_literal: true
+
+module Chat
+  module OutgoingWebHookExtension
+    def self.prepended(base)
+      def base.enqueue_chat_message_hooks(event, payload, opts = {})
+        if active_web_hooks("chat_message").exists?
+          WebHook.enqueue_hooks(:chat_message, event, payload: payload, **opts)
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/chat/plugin.rb b/plugins/chat/plugin.rb
index 1a9789b85b9..0473e0a05f0 100644
--- a/plugins/chat/plugin.rb
+++ b/plugins/chat/plugin.rb
@@ -67,6 +67,7 @@ after_initialize do
     Jobs::UserEmail.prepend Chat::UserEmailExtension
     Plugin::Instance.prepend Chat::PluginInstanceExtension
     Jobs::ExportCsvFile.class_eval { prepend Chat::MessagesExporter }
+    WebHook.prepend Chat::OutgoingWebHookExtension
   end
 
   if Oneboxer.respond_to?(:register_local_handler)
@@ -381,6 +382,35 @@ after_initialize do
     end
   end
 
+  # outgoing webhook events
+  %i[
+    chat_message_created
+    chat_message_edited
+    chat_message_trashed
+    chat_message_restored
+  ].each do |chat_message_event|
+    on(chat_message_event) do |message, channel, user|
+      guardian = Guardian.new(user)
+
+      payload = {
+        message: Chat::MessageSerializer.new(message, { scope: guardian, root: false }).as_json,
+        channel:
+          Chat::ChannelSerializer.new(
+            channel,
+            { scope: guardian, membership: channel.membership_for(user), root: false },
+          ).as_json,
+      }
+
+      category_id = channel.chatable_type == "Category" ? channel.chatable_id : nil
+
+      WebHook.enqueue_chat_message_hooks(
+        chat_message_event,
+        payload.to_json,
+        category_id: category_id,
+      )
+    end
+  end
+
   Discourse::Application.routes.append do
     mount ::Chat::Engine, at: "/chat"
 
diff --git a/plugins/chat/spec/fabricators/outgoing_chat_message_web_hook_fabricator.rb b/plugins/chat/spec/fabricators/outgoing_chat_message_web_hook_fabricator.rb
new file mode 100644
index 00000000000..46c222fe6d8
--- /dev/null
+++ b/plugins/chat/spec/fabricators/outgoing_chat_message_web_hook_fabricator.rb
@@ -0,0 +1,9 @@
+# frozen_string_literal: true
+
+Fabricator(:outgoing_chat_message_web_hook, from: :web_hook) do
+  transient chat_message_hook: WebHookEventType.find_by(name: "chat_message")
+
+  after_build do |web_hook, transients|
+    web_hook.web_hook_event_types = [transients[:chat_message_hook]]
+  end
+end
diff --git a/plugins/chat/spec/integration/outgoing_web_hooks_spec.rb b/plugins/chat/spec/integration/outgoing_web_hooks_spec.rb
new file mode 100644
index 00000000000..a951dc6fd7c
--- /dev/null
+++ b/plugins/chat/spec/integration/outgoing_web_hooks_spec.rb
@@ -0,0 +1,245 @@
+# frozen_string_literal: true
+
+RSpec.describe "Outgoing chat webhooks" do
+  before do
+    SiteSetting.chat_enabled = true
+    SiteSetting.chat_allowed_groups = Group::AUTO_GROUPS[:everyone]
+  end
+
+  describe "chat messages" do
+    fab!(:web_hook) { Fabricate(:outgoing_chat_message_web_hook) }
+    fab!(:user1) { Fabricate(:user) }
+    fab!(:user2) { Fabricate(:user) }
+    let(:message_content) { "This is a test message" }
+    let(:new_message_content) { "This is the edited message" }
+    let(:job_args) do
+      Jobs::EmitWebHookEvent
+        .jobs
+        .map { |job| job["args"].first }
+        .find { |args| args["event_type"] == "chat_message" }
+    end
+    let(:event_name) { job_args["event_name"] }
+    let(:event_category_id) { job_args["category_id"] }
+    let(:payload) { JSON.parse(job_args["payload"]) }
+
+    def expect_response_to_be_successful
+      expect(response.status).to eq(200)
+    end
+
+    def expect_web_hook_event_name_to_be(name)
+      expect(event_name).to eq(name)
+    end
+
+    def expect_web_hook_event_category_to_be(category)
+      expect(event_category_id).to eq(category.id)
+    end
+
+    def expect_web_hook_payload_message_to_match(message:, user:, &block)
+      payload_message = payload["message"]
+
+      expect(payload_message["id"]).to eq(message.id)
+      expect(payload_message["message"]).to eq(message.message)
+      expect(payload_message["cooked"]).to eq(message.cooked)
+      expect(payload_message["created_at"]).to eq(message.created_at.iso8601)
+      expect(payload_message["excerpt"]).to eq(message.excerpt)
+      expect(payload_message["chat_channel_id"]).to eq(message.chat_channel_id)
+      expect(payload_message["mentioned_users"]).to be_empty
+      expect(payload_message["available_flags"]).to be_empty
+      expect(payload_message["user"]["id"]).to eq(user.id)
+      expect(payload_message["user"]["username"]).to eq(user.username)
+      expect(payload_message["user"]["avatar_template"]).to eq(user.avatar_template)
+      expect(payload_message["user"]["admin"]).to eq(user.admin?)
+      expect(payload_message["user"]["staff"]).to eq(user.staff?)
+      expect(payload_message["user"]["moderator"]).to eq(user.moderator?)
+      expect(payload_message["user"]["new_user"]).to eq(user.trust_level == TrustLevel[0])
+      expect(payload_message["user"]["primary_group_name"]).to eq(user.primary_group&.name)
+      expect(payload_message["uploads"]).to be_empty
+
+      yield(payload_message) if block_given?
+    end
+
+    def expect_web_hook_payload_channel_to_match_category(channel:, category:, &block)
+      payload_channel = payload["channel"]
+
+      expect(payload_channel["id"]).to eq(channel.id)
+      expect(payload_channel["allow_channel_wide_mentions"]).to eq(
+        channel.allow_channel_wide_mentions,
+      )
+      expect(payload_channel["chatable_id"]).to eq(category.id)
+      expect(payload_channel["chatable_type"]).to eq("Category")
+      expect(payload_channel["chatable_url"]).to eq(category.url)
+      expect(payload_channel["title"]).to eq(channel.title)
+      expect(payload_channel["slug"]).to eq(channel.slug)
+
+      yield(payload_channel) if block_given?
+    end
+
+    def expect_web_hook_payload_channel_to_match_direct_message(channel:, direct_message:, &block)
+      payload_channel = payload["channel"]
+
+      expect(payload_channel["id"]).to eq(channel.id)
+      expect(payload_channel["allow_channel_wide_mentions"]).to eq(
+        channel.allow_channel_wide_mentions,
+      )
+      expect(payload_channel["chatable_id"]).to eq(direct_message.id)
+      expect(payload_channel["chatable_type"]).to eq("DirectMessage")
+      expect(payload_channel["chatable_url"]).to be_nil
+      expect(payload_channel["chatable"]["users"][0]["id"]).to eq(user2.id)
+      expect(payload_channel["chatable"]["users"][0]["username"]).to eq(user2.username)
+      expect(payload_channel["chatable"]["users"][0]["name"]).to eq(user2.name)
+      expect(payload_channel["chatable"]["users"][0]["avatar_template"]).to eq(
+        user2.avatar_template,
+      )
+      expect(payload_channel["chatable"]["users"][0]["can_chat"]).to eq(true)
+      expect(payload_channel["chatable"]["users"][0]["has_chat_enabled"]).to eq(true)
+      expect(payload_channel["title"]).to eq(channel.title(user1))
+      expect(payload_channel["slug"]).to be_nil
+
+      yield(payload_channel) if block_given?
+    end
+
+    context "for a category channel" do
+      fab!(:category) { Fabricate(:category) }
+      fab!(:chat_channel) { Fabricate(:category_channel, chatable: category) }
+      fab!(:chat_message) { Fabricate(:chat_message, chat_channel: chat_channel, user: user1) }
+
+      before do
+        [user1, user2].each do |user|
+          Chat::UserChatChannelMembership.create(
+            user: user,
+            chat_channel: chat_channel,
+            following: true,
+          )
+        end
+
+        sign_in(user1)
+      end
+
+      it "triggers a webhook when a chat message is created" do
+        post "/chat/#{chat_channel.id}.json", params: { message: message_content }
+
+        expect_response_to_be_successful
+        expect_web_hook_event_name_to_be("chat_message_created")
+        expect_web_hook_event_category_to_be(category)
+        expect_web_hook_payload_message_to_match(
+          message: Chat::Message.last,
+          user: user1,
+        ) { |payload_message| expect(payload_message["message"]).to eq(message_content) }
+        expect_web_hook_payload_channel_to_match_category(channel: chat_channel, category: category)
+      end
+
+      it "triggers a webhook when a chat message is edited" do
+        put "/chat/#{chat_channel.id}/edit/#{chat_message.id}.json",
+            params: {
+              new_message: new_message_content,
+            }
+
+        expect_response_to_be_successful
+        expect_web_hook_event_name_to_be("chat_message_edited")
+        expect_web_hook_event_category_to_be(category)
+        expect_web_hook_payload_message_to_match(
+          message: Chat::Message.last,
+          user: user1,
+        ) { |payload_message| expect(payload_message["message"]).to eq(new_message_content) }
+        expect_web_hook_payload_channel_to_match_category(channel: chat_channel, category: category)
+      end
+
+      it "triggers a webhook when a chat message is trashed" do
+        delete "/chat/api/channels/#{chat_message.chat_channel_id}/messages/#{chat_message.id}.json"
+
+        expect_response_to_be_successful
+        expect(chat_message.reload.trashed?).to eq(true)
+        expect_web_hook_event_name_to_be("chat_message_trashed")
+        expect_web_hook_event_category_to_be(category)
+        expect_web_hook_payload_message_to_match(message: chat_message, user: user1)
+        expect_web_hook_payload_channel_to_match_category(channel: chat_channel, category: category)
+      end
+
+      it "triggers a webhook when a trashed chat message is restored" do
+        chat_message.trash!(user1)
+        expect(chat_message.reload.trashed?).to eq(true)
+
+        put "/chat/api/channels/#{chat_channel.id}/messages/#{chat_message.id}/restore.json"
+
+        expect_response_to_be_successful
+        expect(chat_message.reload.trashed?).to eq(false)
+        expect_web_hook_event_name_to_be("chat_message_restored")
+        expect_web_hook_event_category_to_be(category)
+        expect_web_hook_payload_message_to_match(message: chat_message, user: user1)
+        expect_web_hook_payload_channel_to_match_category(channel: chat_channel, category: category)
+      end
+    end
+
+    context "for a direct message channel" do
+      fab!(:direct_message) { Fabricate(:direct_message, users: [user1, user2]) }
+      fab!(:direct_message_channel) { Fabricate(:direct_message_channel, chatable: direct_message) }
+      fab!(:chat_message) do
+        Fabricate(:chat_message, chat_channel: direct_message_channel, user: user1)
+      end
+
+      before { sign_in(user1) }
+
+      it "triggers a webhook when a chat message is created" do
+        post "/chat/#{direct_message_channel.id}.json", params: { message: message_content }
+
+        expect_response_to_be_successful
+        expect_web_hook_event_name_to_be("chat_message_created")
+        expect_web_hook_payload_message_to_match(
+          message: Chat::Message.last,
+          user: user1,
+        ) { |payload_message| expect(payload_message["message"]).to eq(message_content) }
+        expect_web_hook_payload_channel_to_match_direct_message(
+          channel: direct_message_channel,
+          direct_message: direct_message,
+        )
+      end
+
+      it "triggers a webhook when a chat message is edited" do
+        put "/chat/#{direct_message_channel.id}/edit/#{chat_message.id}.json",
+            params: {
+              new_message: new_message_content,
+            }
+
+        expect_response_to_be_successful
+        expect_web_hook_event_name_to_be("chat_message_edited")
+        expect_web_hook_payload_message_to_match(
+          message: Chat::Message.last,
+          user: user1,
+        ) { |payload_message| expect(payload_message["message"]).to eq(new_message_content) }
+        expect_web_hook_payload_channel_to_match_direct_message(
+          channel: direct_message_channel,
+          direct_message: direct_message,
+        )
+      end
+
+      it "triggers a webhook when a chat message is trashed" do
+        delete "/chat/api/channels/#{chat_message.chat_channel_id}/messages/#{chat_message.id}.json"
+
+        expect_response_to_be_successful
+        expect(chat_message.reload.trashed?).to eq(true)
+        expect_web_hook_event_name_to_be("chat_message_trashed")
+        expect_web_hook_payload_message_to_match(message: chat_message, user: user1)
+        expect_web_hook_payload_channel_to_match_direct_message(
+          channel: direct_message_channel,
+          direct_message: direct_message,
+        )
+      end
+
+      it "triggers a webhook when a trashed chat message is restored" do
+        chat_message.trash!(user1)
+        expect(chat_message.reload.trashed?).to eq(true)
+
+        put "/chat/api/channels/#{direct_message_channel.id}/messages/#{chat_message.id}/restore.json"
+
+        expect_response_to_be_successful
+        expect(chat_message.reload.trashed?).to eq(false)
+        expect_web_hook_event_name_to_be("chat_message_restored")
+        expect_web_hook_payload_message_to_match(message: chat_message, user: user1)
+        expect_web_hook_payload_channel_to_match_direct_message(
+          channel: direct_message_channel,
+          direct_message: direct_message,
+        )
+      end
+    end
+  end
+end
diff --git a/plugins/chat/spec/services/chat/restore_message_spec.rb b/plugins/chat/spec/services/chat/restore_message_spec.rb
index 3f71312212f..e7ce41d715c 100644
--- a/plugins/chat/spec/services/chat/restore_message_spec.rb
+++ b/plugins/chat/spec/services/chat/restore_message_spec.rb
@@ -67,8 +67,11 @@ RSpec.describe Chat::RestoreMessage do
           freeze_time
           messages = nil
           event =
-            DiscourseEvent.track_events { messages = MessageBus.track_publish { result } }.first
-          expect(event[:event_name]).to eq(:chat_message_restored)
+            DiscourseEvent
+              .track_events { messages = MessageBus.track_publish { result } }
+              .find { |e| e[:event_name] == :chat_message_restored }
+
+          expect(event).to be_present
           expect(event[:params]).to eq([message, message.chat_channel, current_user])
           expect(
             messages.find { |m| m.channel == "/chat/#{message.chat_channel_id}" }.data,
diff --git a/plugins/chat/spec/services/chat/trash_message_spec.rb b/plugins/chat/spec/services/chat/trash_message_spec.rb
index cee1ebba4ce..821662433ca 100644
--- a/plugins/chat/spec/services/chat/trash_message_spec.rb
+++ b/plugins/chat/spec/services/chat/trash_message_spec.rb
@@ -62,8 +62,11 @@ RSpec.describe Chat::TrashMessage do
           freeze_time
           messages = nil
           event =
-            DiscourseEvent.track_events { messages = MessageBus.track_publish { result } }.first
-          expect(event[:event_name]).to eq(:chat_message_trashed)
+            DiscourseEvent
+              .track_events { messages = MessageBus.track_publish { result } }
+              .find { |e| e[:event_name] == :chat_message_trashed }
+
+          expect(event).to be_present
           expect(event[:params]).to eq([message, message.chat_channel, current_user])
           expect(messages.find { |m| m.channel == "/chat/#{message.chat_channel_id}" }.data).to eq(
             {
diff --git a/spec/models/web_hook_spec.rb b/spec/models/web_hook_spec.rb
index 196f91a0e0c..f2477cdc6a4 100644
--- a/spec/models/web_hook_spec.rb
+++ b/spec/models/web_hook_spec.rb
@@ -64,6 +64,10 @@ RSpec.describe WebHook do
       SiteSetting.stubs(:voting_enabled).returns(true)
       voting_event_types = WebHookEventType.active.where(name: "topic_voting")
       expect(voting_event_types.count).to eq(1)
+
+      SiteSetting.stubs(:chat_enabled).returns(true)
+      chat_enabled_types = WebHookEventType.active.where("name LIKE 'chat_%'")
+      expect(chat_enabled_types.count).to eq(1)
     end
 
     describe "#active_web_hooks" do