You have 3 reservations in your PMS - all with the same dates of stay, and the same email address.

Obviously, different people will be staying in each room; it's just that each room was booked with the same lead guest.

You want Guest Engagement to send, for example, 3 check-in emails; one for each reservation.

When Guest Engagement receives your reservtion data, we automatically detect "duplicates"; that is, when you have more than one reservation with the same dates of stay, and same email address.

Guest Engagement automatically unsubscribes all but one of those duplicate reservations, ensuring that for example, one person doesn't receive multiple upsell emails about what is to the guest, just one stay.

However, you might actually want multiple emails to be sent to that one address; for example, 3 check-in emails so the details of each guest can be updated.

One way to get past this is to use subaddresses. It's actually very easy.

So, you have 3 separate reservations in the PMS, but all use the same email address.

For example:

What you can do is add a tag to two of those email addresses by editing the address in your PMS as follows:

johnsmith+tagtext@gmail.com

The reservations might look like this:

Note: Technically, it doesn't matter what text you use as the tag, as long as it is different to any other tags you use on that email address.
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That way, Guest Engagement doesn't see these emails as duplicates, but the guest will receive 3 emails, all to the one address - johnsmith@gmail.com

These tags are just some lesser-known functionality in the email world; they aren't universal - meaning not every email provider supports them - but a lot do.

Note that this technique is unlikely to work with OTA masked email addresses.