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You should have the option - tick a box if you want the invoice attached automatically each time for repeating invoices or not. I am a landlord and the annual Council Tax bill for example should automatically be attached so I don't have to manually go into a repeating invoice/bill and reattach.

Ludicrous that the files option exists in the repeating template but doesn't attach to the repeating invoice/bill 😅

this app allows you attach docs to the repeating invoice schedule
Beta testing currently - but there is a sign up at the bottom of the page
https://trimly.app/

As an accounting company whose client insists on their 'service charges summary' be attached to every invoice that is sent out the fact that I cannot send the repeat invoices automatically is HIGHLY frustrating! This means that I have to send 70+ repeating invoices to draft where I then have to attach the file before sending.Please Xero include the functionality of attaching a file on repeating invoices!

How is this not already a thing? It's bleeding obvious and shouldn't have to be asked for.

I was surprised that repeating bills did not include their attachment. It basically makes this function irrelevant as you may as start from scratch rather than having to continually go in manually to reattach the relevant receipt/document.

We send all of our customer invoices as Repeating Invoices to access the Auto Pay feature so saving as a draft first, to then go into each invoice individually for a second time to attach the supporting documentation, is not an option. It is so unprofessional, not to mention time consuming and inefficient, to have to send another copy of the invoice (after it has been paid) to say “oh, by the way, here is the evidence for the charges we collected earlier today”.

We would use Repeating invoices more if we could attach files prior to each being sent, current process is somewhat clunky and has led to delayed invoicing.