There can be a few reasons why an automated message either failed to send to your guest or wasn't scheduled for their reservation in the first place. This article walks through the most common causes, in roughly the order we recommend checking them.
If the message that didn't send was an answer to a question the guest asked, see Question Replies: How to automate answers to guest questions instead.
Where To Start
Before digging into specific causes, run through this short checklist. It resolves the majority of cases on its own.
Check your email for an "Oopsie!" notice. When a message fails to send, Hospitable sends an email to the primary account owner explaining what happened. This is the fastest way to confirm whether Hospitable tried to send the message and what blocked it.
Open the reservation in your Inbox. Find the Activity log on the left-hand side and look for the message. The log will show whether the message was scheduled, sent, cancelled, or never created.
Confirm the messaging rule was enabled and correctly scoped at the time the message was supposed to be created — not just right now. See Scoping below.
Confirm the reservation was actually accepted by the booking platform. Inquiries, requests, and cancelled or declined reservations don't trigger the same messages as accepted bookings.
If those four checks don't explain the issue, continue through the rest of this article.
The Basics
Scoping
Make sure the messaging rule is scoped to the platform and property, as well as the host for the booking channel which the guest booked through.
You can read more about scoping here.
Message content
Different platforms have different criteria for what content they will filter and block, at what stage of the reservation, and what they will block.
If your message breaches the platform's policies, it may be rejected wholly.
See more about permissible message content here.
The reservation was never accepted
Messaging rules are triggered by events from the booking platform — most commonly the Accepted event. If Hospitable never received an Accepted event for the reservation (for example, the booking was never confirmed, or was confirmed before your listing was connected to Hospitable), scheduled messages may fail to be created.
Your Hospitable subscription was not active when the message was due
Automated messages only send while your Hospitable subscription is active or in trial. If your subscription lapsed, was cancelled, or was paused at the moment the message was scheduled to send, the message will not have gone out.
Check the date the message should have been sent against your billing history under Settings > Billing.
The booking channel was disconnected when the message was due
If the Airbnb, Vrbo, or Booking.com account the reservation belongs to was disconnected from Hospitable at the moment a message was scheduled to send, the message will be cancelled. Messages cancelled this way do not automatically resend when the account is reconnected — you'll need to send them manually using the steps further down this article.
You can check the connection status under Settings > Channel Connections.
The reservation was altered after the rule was set up
If a reservation is altered (for example, a date change that makes it shorter, a platform change, or a property change) after the messaging rules were generated, the new reservation details may no longer match the rule's conditions. In that case, the message will not be sent.
After checking the basics above, the rest of this article covers caveats that are specific to event messages versus scheduled messages. Read both Event messages and Scheduled messages if you're not sure which category applies to your rule.
Event Messages
Rule conflicts
Messaging rule conflicts happen when multiple event-based messaging rules are configured for the same event. Only one event messaging rule can be sent per event per reservation.
For example: if you have two or more "New reservation" messaging rules configured, Hospitable will pick one at random to send or schedule. The others will not be sent.
Returning guest
By default, Hospitable does not send the "New reservation" event message to returning guests from Airbnb. You can enable a setting that starts sending the message to returning guests.
Read more here.
Last-minute bookings
Event messages should be sent at their scheduled time (immediately or with a delay) after a new event happens.
If you have a delay on your message, and you manually replied to the guest before the scheduled send time of the message, then we will not send it. This is to avoid repetition.
See more on messages for last-minute bookings here.
"After a new reservation" messaging rule
It's important to remember that this messaging rule is not an event message — it's a scheduled message, with a specific caveat: it will never be scheduled or sent past the check-in time of the reservation.
See more on this messaging rule here.
The event occurred in the past
If you had reservations from your booking platforms which were booked, inquired about, or requested either before you connected that booking platform to Hospitable, or before you created or enabled the relevant event messaging rule, then we will not send that event message out.
Event messages are never sent out retroactively.
New pre-approval message
This messaging rule will never be scheduled or sent to a guest if your "New inquiry" messaging rule is set to "Automatically pre-approve" the guest.
This is because a new inquiry would trigger two messages to fire at the same time. Instead, we recommend hosts include any important information from the "New pre-approval" message in the "New inquiry" message already.
Scheduled Messages
The 9 AM–9 PM send window
To protect guests from late-night notifications, scheduled messages only send between 9 AM and 9 PM in the property's local time zone. If a scheduled message's send time falls outside this window, it is automatically rescheduled to send at the next available time inside the window.
⏰ This restriction applies to scheduled messages only. Event messages (such as New reservation or New inquiry) are always sent at their trigger time, regardless of the time of day.
The guest has not yet signed the rental agreement
If you have rental agreements enabled and the guest has not yet signed, all scheduled messages for that reservation are held back until the agreement is signed. Once the guest signs, held messages will resume sending (subject to the 9 AM–9 PM window described above).
If you don't want messages to be held back this way, you can adjust the rental agreement requirements so signing is not required.
Read more about rental agreements here.
Last-minute bookings
If your guest booked a last-minute stay, close to the check-in and check-out times, and a scheduled message wasn't sent to them, please check the last-minute booking caveats here.
For reservations made after the intended check-in time, check-in instructions are scheduled to be sent 30 minutes after the reservation is accepted. This behaviour is expected, and the send-time cannot be automatically sped up. However, you can manually send the scheduled message earlier if you choose:
Open the conversation page in the Hospitable Inbox.
Find the scheduled message under the "Activity" log on the left-hand side.
Click on the scheduled message.
Click "Send now" on the scheduled message log page.
Before check-out messaging rule send time
If a reservation is booked after the time a Before check-out messaging rule is scheduled to be sent, the message will be cancelled, and not sent.
Specific reservation duration
Scheduled messages can be configured to only be sent for reservations that are a certain number of nights or more.
That is the "Specify a reservation duration" setting.
If this setting is enabled, then the reservation stay must meet the requirement in order for us to schedule the message.
You can read more about settings here.
After a new reservation message
This messaging rule has a specific caveat: it will not be sent if the send time falls after the check-in time on the reservation.
See more here.
Do not send if a guest has published a review
This setting only applies to Airbnb reservations. If enabled, and your guest has already left a review for you on Airbnb, then we will not send this message out.
Read more about this here.
You manually replied to the guest before the send time
If you (or someone on your team) manually sent a message to the guest before a scheduled message's send time, that scheduled message will be cancelled to avoid duplicate or contradictory communication. You can see this in the Activity log on the reservation's conversation page.
Prevention Tips
Avoid including restricted content (e.g., shortened URLs) in your message templates.
Test automated messages with manual test bookings to ensure they function as expected, especially after making adjustments to rules or templates.
Familiarise yourself with platform-specific guidelines (e.g., Booking.com restrictions) to avoid common pitfalls.
If you use rental agreements, make sure your guests have a clear path to sign them, since unsigned agreements will hold back scheduled messages.
How To Send a Message Template Manually To a Guest
If a message was not sent but you still want to send it to the guest, you can do so manually:
Go to Guest Experience > Messaging.
Click on the messaging rule you need to send.
Click Preview message below the message template.
Select the conversation with the guest you need the message for.
Select the text and copy.
Go to the Inbox and click on the conversation with the guest.
Paste the template into the text box and click Send.
FAQs
Why aren't my messages reaching Booking.com guests?
Why aren't my messages reaching Booking.com guests?
A few causes are specific to Booking.com:
URL shorteners are blocked. Booking.com rejects messages that contain shortened URLs (such as bit.ly or tinyurl). Use complete URLs instead.
Restricted content is blocked. Phone numbers, email addresses, and certain other content can cause Booking.com to reject the message with a 403 error.
Your messaging account may not be on Booking.com's allowlist. If you see an in-Inbox error stating that sending a Booking.com message is not allowed, please contact Hospitable support — this can be resolved by our team adding your account to Booking.com's allowlist.
Why didn't a message send to my Vrbo guest?
Why didn't a message send to my Vrbo guest?
Your Vrbo account is disconnected. This is the most common reason. If your Vrbo account has disconnected from Hospitable, all automated messaging to Vrbo guests will stop. Check your connection status under Settings > Channel Connections > Vrbo. If you use the Chrome extension, you'll need to reconnect on a desktop computer. See Resolve Vrbo Account Disconnections for step-by-step instructions.
Vrbo's content filter is blocking your message. Vrbo automatically scans outgoing messages and may reject them if they contain certain content. Known triggers include:
Phone numbers or email addresses
External links or URLs (especially in pre-booking messages)
Payment-related language ("pay," "charge," "fee")
Competing platform names ("Airbnb," "Booking.com")
Numbers in parentheses that resemble phone numbers, e.g. "(3) guests"
If your message was blocked, try removing or rewording the flagged content. For example, instead of writing "The fee is $50," try "The cleaning cost is $50."
Note that pre-booking messages with links are not supported on Vrbo.
How to check if your message was actually sent to a Vrbo guest:
Open the reservation in your Hospitable Inbox and check the message log to see if the message shows as "Sent."
If it shows as sent in Hospitable but the guest says they didn't receive it, log into your Vrbo account directly to verify — Vrbo messages can sometimes take longer to appear than Airbnb messages.
What can cause a scheduled message, like check-in instructions, to not send?
What can cause a scheduled message, like check-in instructions, to not send?
Common causes include:
The "Exclude Last-Minute Bookings" setting being enabled on the rule.
A scoping issue where the correct host is not assigned to the property for the messaging rule.
The guest not having signed the rental agreement yet (when rental agreements are enabled).
The send time falling outside the 9 AM–9 PM window for scheduled messages, causing the message to be rescheduled.
The booking channel account being disconnected at the moment the message was due to send.
Your Hospitable subscription not being active or trialing at the moment the message was due to send.
Address these factors as described in the sections above.
What is the "Oopsie!" email?
What is the "Oopsie!" email?
When Hospitable tries to send an automated message and the send fails, we send the primary account owner an "Oopsie!" notification by email. The email names the reservation and explains what went wrong, so it's the fastest way to confirm whether a message was attempted at all and what blocked it. If you can't find an "Oopsie!" email for a message that didn't send, the message likely was never generated in the first place — see the Where to start checklist at the top of this article.
Can these solutions apply to platforms other than Booking.com?
Can these solutions apply to platforms other than Booking.com?
Yes. While some examples here are specific to Booking.com or Vrbo, the same general troubleshooting approach — checking scoping, rule conditions, message content, and channel/subscription status — applies across Airbnb, Booking.com, Vrbo, and any other connected channel.