You set up Hostaway's automated messages: booking confirmation, check-in instructions, a checkout reminder. Guests still write in all day with questions none of them answered, and your team answers each one by hand.
That is the normal shape of a growing portfolio, not a setup mistake. Automations send predefined messages when configured events occur, including when a guest sends a message. Questions arrive in the guest's own words, at the guest's own time. This guide covers how to get the most out of Hostaway's automations, using Hostaway's help center as the source, and then what to do about the questions they will never cover.
What Hostaway automations do
Per Hostaway's Message Automations article (updated 2026-09-24), an automation sends guest communication based on reservation events and can pull details from the listing and the reservation. You build them under Inbox > Automations, as described in Set Up Message Automations.
The triggers Hostaway documents include a new reservation, guest arrival, guest departure, inquiry, pending reservation, cancellation, awaiting payment, a day of the week and time, a message received, door code created, online check-in form submitted, a published review and pre-authorization success. You choose the channels and listings, and you can add conditions such as number of guests or length of stay.
Setting them up so they send when you expect
1. One automation per topic, not per listing. Hostaway says to create one automation per topic and use fields instead. The dynamic fields list covers guest name, check-in and check-out dates and times, number of guests and pets, listing name, address, door code and guest portal link. A check-in message with fields is one message to maintain, not thirty.
2. Know when the message is created. Hostaway's Message Automations guide says scheduled messages are created when it receives a reservation and sent according to the selected event. Before it goes out you can cancel it, edit it or send it immediately, and an edit applies to that guest only.
3. Expect new automations to reach existing bookings. A new automation can create messages for existing reservations if they are still inside the trigger's timeframe. Hostaway's example: an automation created on the check-in date set to fire at booking will not send, while one set to fire one day before checkout will.
4. Treat the door code with care. The door code article says the code comes from the reservation's Door code field, which you fill by hand unless a smart lock integration or Hostaway's Smartlock feature does it. Hostaway delays door-code messages by up to 15 minutes when the field is empty, to let a lock integration push the latest code, and then falls back to the listing's static code.
5. Allow for timing. The send time article says automations can be set up to 60 days before or after an event, and that delays of up to 30 minutes are expected. For time-sensitive details it suggests scheduling a little ahead of when they are needed, and stating the actual check-in time in the message.
6. Check conditions and channels first when a message does not send. Automated Messages Not Sending lists the common causes: a condition not yet met when the trigger fired, a channel missing from the automation's scope, and channels that do not support messaging, such as Vrbo iCal. Check the trigger type and the Always Trigger setting: per Hostaway's setup guide, with Always Trigger on, a reservation that arrives after check-in but before check-out still gets the message, while one that arrives after check-out does not, and Reservation triggers re-check their conditions when the reservation is updated. Conditions on an automation cannot be changed after it is created, so test the logic on a real upcoming booking before you apply it to every listing.
7. Use the message-received trigger for the gap. Hostaway lets you trigger on a guest message, including only the first message in a thread, or only on set days and hours. That suits an acknowledgement such as "we received your message and will reply by 9 a.m." It acknowledges. It does not answer.
What automations cannot answer
Every item above is about messages you can predict. The questions that keep your team busy are not predictable in wording or timing:
- "Is there a crib, and can you set it up before we arrive?"
- "We land at 1 p.m. Can we drop bags?"
- "The code did not work."
- "Can we extend by one night?"
- "Is the pool heated this week?"
Receiving one of these questions can trigger a predefined message, but the trigger does not determine which answer the guest needs. Some are in your house rules. Some depend on whether the unit is clean yet. Some need a person. A broader template does not fix this: a message that tries to cover everything gets long, and guests skip long messages and write anyway.
A practical habit is to keep a tally for two weeks of every question that arrives after an automation went out. Sort it into three piles: answered by a fact about the unit (add it to the check-in message or the guest portal), answered by the state of the stay (needs the booking and the turnover), and needs a person. The first pile shrinks your message volume. For questions that depend on booking or listing facts, review Hostaway AI Replies. Route requests that need approval or unavailable operational information to your team.
Illustrative example
This scenario is illustrative, not a customer story. A guest has your check-in message with the door code and parking. At 11 a.m. on arrival day they write: "We are early, around 1 p.m. Is the apartment ready?"
The automation already ran. The answer is not in it. It depends on the reservation (check-in is at 4 p.m.), on whether checkout happened that morning, and on whether the cleaner has finished. A reply that quotes the policy is accurate and unhelpful. A reply that says the team will confirm once the clean is done, and sends the question to the team with the arrival time attached, is the useful one.
How InnSync answers the rest
InnSync is the operations layer around your PMS. Carmen, InnSync's AI agent, answers guest questions from the booking, the unit's details and your house rules, and brings your team in when a situation needs a person. You choose, per channel, whether she replies on her own or drafts for review. Behind the reply sits the routine that follows each reservation: cleaning confirmed with photo proof, check-in requirements, and exceptions handed to the right person with context.
Your Hostaway automations keep doing what they do well: the scheduled, predictable messages. InnSync handles the questions that arrive outside the schedule.
If you use Hostaway
Keep Hostaway. InnSync runs the operation around it — the connection is set up with you during onboarding.
See InnSync for Hostaway.