Why do my messages show 'failed to send'?

When you send a message through the Hosthub Inbox and see a "failed to send" error, it means the channel (Airbnb, Booking.com, etc.) rejected the message. Messages are always delivered through the channel's own messaging system, so their rules control what content is allowed. When a message fails, the Inbox usually displays a notice explaining exactly why it was rejected, so you can adjust and resend.

The most common causes are links, file attachments, and rich text formatting.

Links in messages

Channels often block messages that contain URLs.

• Airbnb: Links are not allowed in messages for inquiries and booking requests. Forwarding a personal or external website so a guest can book directly (outside the platform) is not permitted. Airbnb also frequently blocks links at the inquiry stage, before a booking is confirmed — even a clean, legitimate link (e.g. a OneDrive or Google Drive URL) can fail at that stage.
• Booking.com: Messages containing links are blocked by default. You can allow specific links by whitelisting the URLs in the Booking.com extranet (see the "Whitelisting URLs for booking.com messages" article).

What you can do:

• Before a booking is confirmed, send a plain text message without the link (e.g. "I can share the floor plan once the booking is confirmed").
• After confirmation, send the shareable link.

File attachments (images, PDFs)

File attachments such as images, JPEGs, and PDFs cannot be sent directly through the Inbox or automated messages. Attempting to send them results in a "failed to send" error. This is expected behavior — Airbnb messages sent through the Inbox do not support attachments.

How to share a file instead:

1. Upload the file to Google Drive, Dropbox, or OneDrive.
2. Set the file so that "Anyone with the link can view."
3. Copy the shareable link.
4. Paste the link directly into your message as plain text (keep the message simple, e.g. "Here's the floor plan: https://...").

Remember that links themselves may still be blocked before a booking is confirmed (see above), so it may be necessary to wait until after confirmation.

Rich text / HTML formatting

Airbnb's messaging system does not support HTML or rich text formatting. Avoid copying text from Word or email, as it can carry hidden formatting that causes the message to fail. Type the message fresh in the Inbox as plain text.

Quick checklist when a message fails

• Read the error note in the Inbox — it usually states exactly what the channel rejected.
• Remove any file attachments and share files via a link instead.
• Use plain text only (no HTML/rich text).
• For Booking.com, whitelist the URL in the extranet.
• For Airbnb, avoid links at the inquiry stage; send them only after the booking is confirmed.
• Try refreshing the page if the Inbox is not letting you send at all.

Updated on: 22/07/2026