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dea
When invoices are imported from Dext, Xero creates the invoice with the original PDF attached — but it doesn’t automatically include that attachment when the invoice is emailed to the client.

Right now, I have to open each invoice and manually tick “Include attachments” just so the customer gets the itemised PDF. This takes ages when processing lots of invoices and makes it easy to miss one.

What I’d like
A simple setting that lets Xero:

Automatically include the imported PDF attachment when sending invoices created via Dext (or any other integration)

Allow users to override/remove it on individual invoices if needed

Why this helps

Saves loads of time

Ensures customers always receive the itemised invoice they expect

Reduces mistakes

Makes the Dext → Xero workflow smoother and more automated

We are uploading invoices to Hubdoc, which then get processed as Invoice (AR) to a draft invoice in Xero. After approval we email the invoices in bulk to our customers and tick the box "Include files as attachments". The uploaded invoice file however is not included in the email. How do we fix this without needing to open each individual invoice and selecting "include with online invoices" in the files section in the invoice?

It should be a must-have feature to avoid mistakes by not manually ticking the option

Having read lots of comments and suggestions on this thread, it make me wonder - again - why Xero won't listen to our needs and insists on doing things their way rather than for the greater good. Perhaps they should consider who pays their wages!

This would be really useful for us

Ability to automatically tick the 'include with online invoice' option when attaching files to an invoice.
It would be useful to choose in the invoice settings or something the ability to 'automatically include all attached files when emailing invoices'

Ability to automatically tick the 'include with online invoice' option when attaching files to an invoice.
When attaching multiple files to an invoice, I find it tends to only tick that option for the newest file (which I can understand). However, it would be great to choose in the invoice settings or something the ability to 'automatically include all attached files when emailing invoices'

This is essential for how our business works, as the attached files are always the signed orders and authorisations that have to go out with the invoice. It is fiddly to set each individual file to attach to an invoice, as there can be 20-30 attached signed slips.

Having to select attach a file on the invoice page and then tick another box on the email page to include the file is not necessary. If it is ticked on the invoice page, can it not automatically be ticked on the next page to be sent with the invoice?

I would love to be able to attach the company's trade terms to all invoices. Trade terms are an important legality that every customer needs to be able to see. Sending trade terms as a separate document is pointless, but having the terms on the invoice gives customers no excuse to read them.

When following a file through from uploads to sale invoice, and you click on the arrow to 'include upload on invoice' be able to either one click include all uploads, or just make in default. Why would you be uploaded a document if you didn't want to attach it?
Such a faff.

Hi team, I think I may have missed the announcement to this thread, but it looks like the functionality within Xero has now changed that it remembers what you did last time when emailing an invoice? I've noticed that when I go to send invoices now, if there is a file marked to be attached in the main invoice screen, it now populates the tick box in the send email screen which is awesome!
Thanks so much for that, any chance that the final part of this, having Xero remember what my preference is when attaching files in the invoice screen and automatically populate that tick box as well please?

Why cant we have our terms and conditions upload automatically with all quotes and invoices
NO BRAINER!!!!!
So many boxes and stuff to click when your in a rush for a simple task
THEY HAVE TO BE THERE FOR ALL CONTACT WITH CLIENTS

And why dose the discripton box fully light up when you click into the box
When writing up a full quote you can easily delete it without knowing
Drives me mad. Again in a hurry...........
The price box dosnt do it?

And I dont feel spell check would go astray

Especially in the email zone

Cheers

This has caused considerable inefficiency and confusion for both our clients and ourselves. Leading to a duplication of work and it has introduced an element of doubt into our interactions with a range of finance departments. This erodes trust and looks bad for our company name as well as for Xero as an effective finance system. I struggle to understand why I would want to attach something and not have it sent? I appreciate there may be some function or need where people may want to attach something and not send, but this doesn't fit our needs. I would be grateful if attach with invoice could be set to default. And the option to not attach to be selected. I appreciate you may get a similar level of dissatisfaction from a as yet unheard audience who wish to attach things and not send. Please let us know if you make changes as we have had to redo a whole invoice run. Poor comms on the part of Xero.

In addition to the other Vote around this area, we do not want Send Copy invoice automatically selected as a default.

It would be great to have the spec sheets that are added as a file to the product automatically attached.
Also super handy for Terms of Trade

Hi team, I do like the layout of the new invoicing, and get that moving a customer base the size that Xero has across to a new platform for probably the most widely used feature outside of bank rec would have been a massive undertaking, but the fact that new invoicing doesn't let me configure whether I want to attach files as a default when sending invoices is a big issue for my business.
I know I should just remember to check that the box is ticked before sending an invoice, but to me good software is something that remembers things like that for me as a user.
I understand the cost of implementing a feature that may not be so critical or important to people can be prohibitive, and can see that only 216 people have voted for this one so suspect it's probably further down your list, but do you have any idea please of when you might be able to fix this please?
Every time I forget I have to resend the invoice to my client, then take more time to write an email to apologise to them for my mistake, then chastise myself for actually making the mistake, and finally end up here wondering when Xero will be able to solve this for me :)
Is there any light at the end of this tunnel for me please?

If I am attaching a pdf to an invoice I am sending out - why do i have to Tick attach to online and then again click attach pdf as an attachment - can this be defaulted to always attach and if people attach something and don't want to send it - they untick it!! surely these extra ticks are frustrating others - why else do you add an attachment if you don't want to send it?

This would be very important for our client that sends invoices from a seperate invoicing system but uses Xero for statements & accounts. It would save time from needing to send the invoices customers hadn't received which would ultimately mean they get paid faster.

Yes please - this is useful for proof of delivery

This is critical for our clients