diff --git a/.changeset/empty-tables-change.md b/.changeset/empty-tables-change.md
new file mode 100644
index 00000000000..c79b473ecbd
--- /dev/null
+++ b/.changeset/empty-tables-change.md
@@ -0,0 +1,5 @@
+---
+"@rocket.chat/meteor": patch
+---
+
+Fixes the condition for firing the `LivechatSessionTaken` webhook event.
diff --git a/apps/meteor/app/livechat/server/lib/hooks.ts b/apps/meteor/app/livechat/server/lib/hooks.ts
index 1a942e77ce8..0431d022a18 100644
--- a/apps/meteor/app/livechat/server/lib/hooks.ts
+++ b/apps/meteor/app/livechat/server/lib/hooks.ts
@@ -114,7 +114,7 @@ export const onNewRoom = makeFunction(async (room: IOmnichannelRoom) => {
 
 export const afterTakeInquiry = makeFunction(
 	async ({ room }: { inquiry: InquiryWithAgentInfo; room: IOmnichannelRoom; agent: { agentId: string; username: string } }) => {
-		if (settings.get('Livechat_webhook_on_chat_taken')) {
+		if (!settings.get('Livechat_webhook_on_chat_taken')) {
 			return;
 		}
 		await sendToCRM('LivechatSessionTaken', room);
diff --git a/apps/meteor/tests/end-to-end/api/livechat/06-integrations.ts b/apps/meteor/tests/end-to-end/api/livechat/06-integrations.ts
index bcdee0666dc..9937af8d6ce 100644
--- a/apps/meteor/tests/end-to-end/api/livechat/06-integrations.ts
+++ b/apps/meteor/tests/end-to-end/api/livechat/06-integrations.ts
@@ -1,10 +1,19 @@
-import type { ISetting } from '@rocket.chat/core-typings';
+import type { IOmnichannelRoom, ISetting } from '@rocket.chat/core-typings';
 import { expect } from 'chai';
 import { after, before, describe, it } from 'mocha';
 import type { Response } from 'supertest';
 
 import { getCredentials, api, request, credentials } from '../../../data/api-data';
-import { deleteVisitor } from '../../../data/livechat/rooms';
+import {
+	closeOmnichannelRoom,
+	createAgent,
+	createLivechatRoom,
+	createVisitor,
+	deleteVisitor,
+	getLivechatRoomInfo,
+	startANewLivechatRoomAndTakeIt,
+} from '../../../data/livechat/rooms';
+import { sleep } from '../../../data/livechat/utils';
 import { updatePermission, updateSetting } from '../../../data/permissions.helper';
 
 describe('LIVECHAT - Integrations', () => {
@@ -138,7 +147,86 @@ describe('LIVECHAT - Integrations', () => {
 				await request.post(api('livechat/webhook.test')).set(credentials).expect(400);
 			});
 		});
+
+		describe('Webhook notifications', () => {
+			before(async () => {
+				await updateSetting('Livechat_webhookUrl', `${webhookUrl}/anything`);
+				await updateSetting('Livechat_Routing_Method', 'Manual_Selection');
+				await createAgent();
+			});
+			after(async () => {
+				await updateSetting('Livechat_webhookUrl', '');
+				await updateSetting('Livechat_Routing_Method', 'Auto_Selection');
+				await updateSetting('Livechat_webhook_on_start', false);
+				await updateSetting('Livechat_webhook_on_close', false);
+				await updateSetting('Livechat_webhook_on_chat_taken', false);
+				await updateSetting('Livechat_webhook_on_chat_queued', false);
+			});
+
+			it('should send a notification on chat start', async () => {
+				await updateSetting('Livechat_webhook_on_start', true);
+
+				const { room } = await startANewLivechatRoomAndTakeIt();
+				await sleep(1000);
+
+				const roomInfo = await getLivechatRoomInfo(room._id);
+
+				expect(roomInfo.crmData).to.be.an('string');
+				expect(JSON.parse(roomInfo.crmData as string))
+					.to.have.property('json')
+					.that.has.property('type', 'LivechatSessionStart');
+				await updateSetting('Livechat_webhook_on_start', false);
+				await closeOmnichannelRoom(room._id);
+			});
+			it('should send a notification on chat taken', async () => {
+				await updateSetting('Livechat_webhook_on_chat_taken', true);
+
+				const { room } = await startANewLivechatRoomAndTakeIt();
+				await sleep(1000);
+
+				const roomInfo = await getLivechatRoomInfo(room._id);
+
+				expect(roomInfo.crmData).to.be.an('string');
+				expect(JSON.parse(roomInfo.crmData as string))
+					.to.have.property('json')
+					.that.has.property('type', 'LivechatSessionTaken');
+				await updateSetting('Livechat_webhook_on_chat_taken', false);
+				await closeOmnichannelRoom(room._id);
+			});
+			let room: IOmnichannelRoom;
+			it('should send a notification on chat queued', async () => {
+				await updateSetting('Livechat_webhook_on_chat_queued', true);
+
+				const visitor = await createVisitor();
+				room = await createLivechatRoom(visitor.token);
+				await sleep(1000);
+
+				const roomInfo = await getLivechatRoomInfo(room._id);
+
+				expect(roomInfo.crmData).to.be.an('string');
+				expect(JSON.parse(roomInfo.crmData as string))
+					.to.have.property('json')
+					.that.has.property('type', 'LivechatSessionQueued');
+				await updateSetting('Livechat_webhook_on_chat_queued', false);
+			});
+			it('should send a notification on chat close', async () => {
+				await updateSetting('Livechat_webhook_on_close', true);
+
+				await closeOmnichannelRoom(room._id);
+
+				await sleep(1000);
+
+				const roomInfo = await getLivechatRoomInfo(room._id);
+
+				expect(roomInfo.crmData).to.be.an('string');
+				expect(JSON.parse(roomInfo.crmData as string))
+					.to.have.property('json')
+					.that.has.property('type', 'LivechatSession');
+				await updateSetting('Livechat_webhook_on_close', false);
+			});
+		});
 	});
+
 	describe('omnichannel/integrations', () => {
 		describe('POST', () => {
 			it('should update the integration settings if the required parameters are provided', async () => {