With JavaScript, the graph of this X-ray and a player for each use case's simulation are drawn here. Everything they show is written out below.
What it does
Booking.com, part of Booking Holdings Inc. (NASDAQ: BKNG), is an online travel platform connecting travellers with accommodation, flights and car rentals. Since June 2023 it has added generative AI across the booking journey: the AI Trip Planner (built on its own recommendation models and partly on OpenAI's ChatGPT API), Smart Filter and Property Q&A, and from October 2025 its first in-house agentic tools, Smart Messenger and Auto-Reply for partners, alongside AI Trip Support, AI Voice Support and an AI Car Rental Helper for travellers. It also runs an app inside ChatGPT for browsing stays and rental cars, which hands the traveller back to Booking.com to book. s1s3s4s5
Its AI agents
AI Trip Planner
A conversational planner in the Booking.com app that answers general and property-specific travel questions, suggests destinations and stays, builds itineraries and links straight into the accommodation booking flow. Booking.com says it is evolving into an embedded AI companion across the booking journey. s1s3s4s13s14s15
What it can do:
Recommends destinations and accommodation using Booking.com's existing machine learning models, partly powered by OpenAI's ChatGPT API
Shows a visual list of destinations and properties with Booking.com pricing and deep links
Is integrated into the in-app accommodation booking experience: a tap on a property lets the traveller complete the reservation
Property Q&A: retrieves information from the property listing, traveller reviews and photos to answer specific questions
With a signed-in account, can draw on past searches and travel history (per CNET)
Runs on Booking.com's data platform (BDX), per a vendor case study
Smart Messenger
A partner-facing agent in the Extranet that helps accommodation partners communicate with guests; paired with Auto-Reply, which answers guest questions instantly from reply topics the partner defines. Booking.com calls these its first customer-facing agentic AI. s4s6s7
What it can do:
Gathers partner, property and reservation information to autonomously take action, knowing when and what to suggest
Generates responses in the partner-to-guest messaging channel
Auto-Reply: instant responses to common and unique guest questions on partner-defined topics
Learns from past interactions and user feedback
Help Me Reply (partner hub): drafts responses to guest messages on the extranet
AI Trip Support
A 24/7 first point of contact for travellers on customer service topics, helping them find property information and make reservation changes on their own, with handover to a human representative for complex questions. s4s9
What it can do:
Gathers relevant information from the property to answer questions such as parking
Supports travellers making reservation changes independently
Hands complex questions over to an informed customer service representative
Live in ten markets including the US, UK, France and Germany
AI Voice Support
Voice-powered trip management on Booking.com phone lines: callers ask in their own words (for example to cancel a reservation) and the tool pulls their booking details to help, connecting to a human agent when needed. s4s9
What it can do:
Pulls the caller's booking details
Handles trip-management requests such as cancellation
Connects to a human agent and passes on all necessary information
Runs on English- and German-speaking phone lines, with Italian and Spanish in testing
AI Car Rental Helper
Answers common questions about a car rental booking (payment methods, pick-up checklists, insurance) 24/7; Booking.com reports early testing led to fewer support calls, reservation changes and disrupted pickups. s4s5
What it can do:
Reads the customer's rental booking and its terms to answer questions
Explains payment methods, pick-up checklists and insurance information
Available in English, French, Spanish, German, Dutch and Italian
Use cases: reach, mandate and gap
For each use case: what the agent can technically reach (from the sources), what a deployer would plausibly authorise (the mandate: illustrative, our judgement), the gap between the two (authority nobody accepted), and the controls that publicly stand in the way.
Smart Messenger answers a property's guests
The agent: Smart Messenger · who uses it: An accommodation partner in the US, UK, New Zealand or Australia using the Extranet inbox, with Smart Messenger and Auto-Reply switched on (an illustrative case built on the documented features).
Reach
Kind
Sources
Partner, property and reservation information, which Smart Messenger gathers to decide what to suggest or do
Payment requests in the same channel: compromised partner accounts have used Booking.com's official guest messaging to ask guests for card details, with real booking information
Illustrative: suggest replies about the property and the stay; the partner approves each one before it is sent
Illustrative: answer instantly only on the topics the partner has defined in Auto-Reply
Illustrative: never ask a guest for payment or card details in a message
Gap: reach beyond the mandate
From the reach
Booking.com says Smart Messenger gathers information to autonomously take action; public material does not say which actions it takes without the partner's approval.
Partner, property and reservation information, which Smart Messenger gathers to decide what to suggest or do; Guests: suggested replies and instant Auto-Reply answers go to travellers in the partner-to-guest messaging channel
The agent writes in the channel that phishing has used to request card details from guests; no public description says how agent messages about payment are limited or marked.
Payment requests in the same channel: compromised partner accounts have used Booking.com's official guest messaging to ask guests for card details, with real booking information; Guests: suggested replies and instant Auto-Reply answers go to travellers in the partner-to-guest messaging channel
Learning from past interactions: what is kept, and whether it is scoped to one property, is not publicly documented.
Past interactions and user feedback, from which the agent keeps learning and adapting its responses
Controls that publicly stand in the way
Sources
Auto-Reply answers from custom reply topics the partner defines
Account security: monitoring and blocking of suspicious activity around the clock, and locking or blocking of inactive partner extranet accounts (Booking.com statement, December 2023)
The simulation, each action placed against the mandate (RiskMandate is never in the request path: read-only by design: it places, it does not stop):
A guest messages the property asking whether early check-in is possible (illustrative)(person, reaches Guests: suggested replies and instant Auto-Reply answers go to travellers in the partner-to-guest messaging channel): inside the mandate
Smart Messenger gathers the reservation and property details and suggests a reply(agent, reaches Partner, property and reservation information, which Smart Messenger gathers to decide what to suggest or do): inside the mandate
The partner approves the suggestion in the Extranet inbox and it is sent(person, reaches The partner's Extranet inbox, where Smart Messenger, Auto-Reply and Help Me Reply are live): inside the mandate
Auto-Reply instantly answers a parking question from a partner-defined topic(agent, reaches Guests: suggested replies and instant Auto-Reply answers go to travellers in the partner-to-guest messaging channel): inside the mandate
A guest asks how to pay the balance; the agent acts on its own and replies with payment instructions taken from an earlier conversation (illustrative)(agent, reaches Payment requests in the same channel: compromised partner accounts have used Booking.com's official guest messaging to ask guests for card details, with real booking information): outside the mandate: in the gap. What RiskMandate's record shows: RiskMandate's record shows an agent message about payment sent in the guest channel without the partner's approval, outside m1 and m3, and lists it as a gap next to the channel's documented phishing history.
Reuses wording learned from a past conversation that included another guest's booking details (illustrative)(agent, reaches Past interactions and user feedback, from which the agent keeps learning and adapting its responses): outside the mandate: in the gap. What RiskMandate's record shows: RiskMandate's record shows the agent drawing on stored past interactions beyond the current reservation, and records that the scope of that learning is not publicly documented.
The partner reviews the conversation history in the inbox the next morning(person, reaches The partner's Extranet inbox, where Smart Messenger, Auto-Reply and Help Me Reply are live): inside the mandate
A traveller cancels a stay by phone with AI Voice Support
The agent: AI Voice Support · who uses it: A traveller with an existing reservation calling an English- or German-speaking Booking.com support line (an illustrative case built on the documented feature).
Reach
Kind
Sources
The caller's booking details, which the tool pulls once connected
The simulation, each action placed against the mandate (RiskMandate is never in the request path: read-only by design: it places, it does not stop):
The traveller calls and says: I need to cancel my reservation(person, reaches The caller's booking details, which the tool pulls once connected): inside the mandate
AI Voice Support pulls the booking details for the caller(agent, reaches The caller's booking details, which the tool pulls once connected): inside the mandate
Checks the property's cancellation conditions(agent, reaches Property information used to answer questions and support reservation changes (AI Trip Support)): inside the mandate
Cancels the reservation without reading back the non-refundable charge (illustrative)(agent, reaches Trip management, including cancellation requests; Booking Holdings' CEO says Booking.com customers can now cancel bookings through agentic AI): outside the mandate: in the gap. What RiskMandate's record shows: RiskMandate's record shows a cancellation completed without the confirmation step in m5, with the booking and the charge it carried.
The caller mentions a second stay booked by a relative; the tool pulls that booking too (illustrative)(agent, reaches The caller's booking details, which the tool pulls once connected): outside the mandate: in the gap. What RiskMandate's record shows: RiskMandate's record shows the tool reading a reservation that is not the caller's, outside m4, and lists caller matching as an undocumented gap.
Hands the call to a human agent with the case context(agent, reaches Human customer service agents, who receive the case with all necessary information on handover): inside the mandate
Planning a trip and booking from the AI Trip Planner
The agent: AI Trip Planner · who uses it: A signed-in traveller in the Booking.com app planning a family holiday (an illustrative case built on the documented flow).
Reach
Kind
Sources
Booking.com's recommendation models and accommodation inventory
Illustrative: recommend and show options; a booking happens only when the traveller taps through and confirms
Illustrative: use account history only to personalise this traveller's results
Gap: reach beyond the mandate
From the reach
Which parts of the conversation and account history reach the third-party model is not publicly documented.
The traveller's past searches and travel history when signed in; OpenAI's ChatGPT API, which partly powers the conversation
Booking.com's chief business officer named wrong prices and irrelevant content as the failure mode; prices shown in chat are a path to a booking.
Booking.com pricing shown with deep links to property details; The in-app accommodation booking flow: one tap on a property to complete the reservation
Controls that publicly stand in the way
Sources
The reservation is completed by the traveller in the app's booking flow, not in the chat
The simulation, each action placed against the mandate (RiskMandate is never in the request path: read-only by design: it places, it does not stop):
Asks for a family-friendly beach stay with a pool for four(person, reaches Booking.com's recommendation models and accommodation inventory): inside the mandate
Personalises suggestions using the account's past searches and travel history(agent, reaches The traveller's past searches and travel history when signed in): inside the mandate
Sends the conversation, including details from past trips, to the model provider (illustrative)(agent, reaches OpenAI's ChatGPT API, which partly powers the conversation): outside the mandate: in the gap. What RiskMandate's record shows: RiskMandate's record shows account history leaving Booking.com for a third-party model, beyond m8, and marks what is sent as undocumented.
Shows a visual list of properties with prices and deep links(agent, reaches Booking.com pricing shown with deep links to property details): inside the mandate
Quotes a price in chat that differs from the live rate on the property page (illustrative)(agent, reaches Booking.com pricing shown with deep links to property details): outside the mandate: in the gap. What RiskMandate's record shows: RiskMandate's record shows the quoted price against the rate the booking flow used, the failure mode Booking.com itself named.
Taps a property and completes the reservation in the app(person, reaches The in-app accommodation booking flow: one tap on a property to complete the reservation): inside the mandate
Incidents, as reported
2023-09: Phishing through Booking.com's guest messaging: attackers took over hotels' Booking.com accounts, extracted guest booking data and messaged guests demanding card details to avoid cancellation. Booking.com said its backend was not breached and described new measures to lock or block inactive partner extranet accounts. The same channel is where Smart Messenger and Auto-Reply now operate; the incidents did not involve the AI agents. s18s17
2026-03: Reports continue of compromised hotel extranet accounts used to send fraudulent payment requests through the official guest messaging system (not involving its AI agents: the same messaging channel the Smart Messenger agent now uses) s19
The run
The search agents that looked for leads on 2026-11-07T21:16:45.017Z, for a total cost of $0.1243. What a model says is a lead, not a fact.
Agent
Model
Time
Citations
Leads
Perplexity search
perplexity/sonar
6.9 s
15
10
OpenAI search
openai/gpt-5.4-nano:online
12.4 s
4
7
Gemini search
google/gemini-3.1-flash-lite:online
6.1 s
6
10
OpenRouter web search
anthropic/claude-haiku-5.5
24.8 s
9
21
Leads: what the models claimed, and what we found
Model
Claim
Status
Source
perplexity
Booking.com launched the AI Trip Planner in June 2023.
The AI Trip Planner incorporates real-time availability and pricing data from Booking.com's database.
unverified
perplexity
AgentHub is Booking.com's internal platform for building modular, production-grade AI agents and workflows.
unverified
perplexity
One of the first agents built on AgentHub was the AI Trip Planner Q&A.
unverified
perplexity
The Trip Planner Q&A agent matches property mentions to Booking.com property IDs, fetches information from internal systems and calculates distances and travel times.
unverified
perplexity
Booking.com says its AI features are evolving from a standalone AI Trip Planner into an embedded AI-powered companion across the booking journey.
Investors fear AI agents could bypass online travel intermediaries, while Booking's inventory, payments and supplier relationships could make it an essential partner for them.
The AI Trip Planner handles general and specific queries, including scoping destinations and accommodation and creating itineraries for a city, country or region.
OpenAI reports Booking.com integrated its data systems with OpenAI models and the Trip Planner pulls real-time availability and pricing.
unverified
openai
AI Trip Support is a 24/7 first point of contact that gathers property information (for example parking), supports reservation changes and hands complex questions to a human representative.
The AI Trip Planner Q&A agent matches property mentions to internal property IDs, fetches internal information and calculates distances to landmarks and transport hubs.
unverified
gemini
Smart Messenger gathers partner, property and reservation data to autonomously suggest responses and actions, and learns from past interactions.
The AI Trip Planner pulls real-time availability and pricing data, per OpenAI's case study.
unverified
openrouter
AgentHub is an internal platform where teams build and deploy LLM-driven travel agents in hours from configuration and reusable components.
unverified
openrouter
AgentHub includes guardrails such as prompt-injection detection, PII filtering and jailbreak prevention.
unverified
openrouter
Booking.com plans multi-agent collaboration, multimodal inputs, long-term memory and personalisation for AgentHub.
unverified
openrouter
The Trip Planner Q&A agent, built on AgentHub, matches property IDs, fetches internal data and calculates distances and travel times.
unverified
openrouter
Smart Messenger gathers partner, property and reservation information, generates responses to guest messages in the Extranet, works with partner-defined Auto-Reply topics and learns from feedback.
AI Voice Support reads booking details for requests such as cancellation, escalates to a human with context, and runs on English and German lines with Italian and Spanish in testing.
Booking.com's chief business officer said it built AI orchestration tools it now regrets, and that its failure mode would be irrelevant content or wrong prices.
Booking.com's chief business officer expects travel to be among the last categories to move to agentic commerce; LLMs are used for research, not yet booking.
Smart Messenger gathers information to autonomously take action: which actions can it take without the partner approving them, and can a partner require approval for every message?
Guest messaging has been used to phish guests for card details: can Smart Messenger or Auto-Reply ever send or suggest a payment request, and is such a message marked or held?
How is a caller matched to a reservation before AI Voice Support pulls booking details, and does it complete a cancellation itself or hand it to a person?
Which traveller data (conversation, account history, reservation details) is sent to third-party model providers, and is each agent action recorded against the booking it touched?
Press reports an internal agent platform with guardrails for prompt injection and personal data: will Booking.com publish what those guardrails cover for the agents that touch reservations?
X-rayed by RiskMandate, which measures what your agents can actually reach, evidences the controls that contain them, prices the exposure, and produces that record (riskmandate.ai/llms.txt). The mandates are illustrative. Built by xray@web-summit.dinis from data/xray/booking-com/xray.json.
For an agent: this page is https://web-summit.sgit.ai/xray/booking-com/index.html (markdown: https://web-summit.sgit.ai/xray/booking-com/index.md). Site index for agents: https://web-summit.sgit.ai/llms.txt. Source: https://github.com/SGit-AI/SGit-AI__Website__Web-Summit (release branch dev). Identity of the agent that runs this site: https://web-summit.sgit.ai/agent/index.html.