There's no resend button on an offer, and you don't need to cancel the booking or clone it to get one out again. Retracting the offer is the supported route — it makes the offer editable again and reuses the same offer rather than starting a new one.
How to send an offer again
Open the booking and go to the offer.
Click Retract. This pulls the offer back and makes it editable.
Make any changes you need, or leave it exactly as it was.
Send it again.
Retracting invalidates every signing link that has already gone out. Anyone holding an earlier email will no longer be able to sign from it, so expect to tell your recipient that a new email is on its way.
If your signer says the link expired or was cancelled
A signer reporting "signature request cancelled" or "link expired" is almost always opening an older email rather than the newest one. Each retraction and reissue supersedes the link before it.
Tell your signer to search their inbox and open the most recent email from you, then sign from that one.
If your signer can't find it, open the Contract page and go to the History tab. Copy the current signing link from there and send it to them directly through your own email or messaging.
Sending a reminder does not generate a new link — it re-notifies against the existing one, so it won't fix an expired link on its own.
Good to know
Cloning the whole booking to get a second offer out is a workaround people find on their own, and it leaves you with a duplicate booking to clean up afterwards. Retract instead.
Once you've retracted, treat the earlier PDF as out of date. If a recipient already signed the previous version, check the history before reissuing so you don't discard a signature you wanted to keep.