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Because the New Invoicing doesn't record when an invoice is re-sent once the 'Sent' box is ticked, that box needs to be unticked if you want Xero to automatically record where and when an invoice has been sent (as it used to under Classic Invoicing). To enable the record to be added to the History of the Invoice, the 'Sent' box must first be unticked.
However, if that invoice relates to a Locked/Closed period, the period first needs to be unlocked.
To resolve this, either the 'Sent' box function is uncoupled from whether the period is locked or not. Or the History and Notes automatically records whenever an Invoice is sent without having to untick the 'Sent' box.
This used to work seamlessly in the Classic invoicing.

Is there any update on this? Currently there is one notification that pops up that says the document can't be edited because it is in a locked period (clearly we're not actually trying to edit the invoice itself just the record associated with it), but then underneath is another notification saying 'invoice sent'. Nothing appears in the notes, so I have to assume it hasn't sent, but if it has, I am going to really annoy my customer by sending another reminder once I've unlocked the period to send it.

This is crazy. We've had this problem too. Surely everyone sends copies of invoices when one is overdue? We certainly need to be able to send the email from in Xero & for there to be a record of having done so. The current method does not record that the invoice has been followed up & therefore we need to make a note - another wasted of our time for something that we used to be able to do automatically.