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Thanks for all the feedback and detail on your needs in the idea here. As you'll see from each others comments there are different points at which businesses would want to be automating this process. Not really a one size fits all approach.
As noted in recent comments, we recently made a change for new invoicing flow where (like classic) you can now choose to Send receipt from the payment confirmation that's shown once you apply a payment to an invoice.
At this time we don't have plans for automating this flow however we're still attuned to the idea here and will be sure to share if there are any plans made toward this in the future.
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So, I am paying extra to use the expenses app, applying the expense to a customer and the billablae expenses account. I also include the receipt of course, which I have to provide to the customer to be reimbursed. So, when I generate an invoice and add a billable expense, the expense is listed but the receipt isn't attached. Am I doing something wrong or is this not available? I can't imagine it wouldn't be because it undermines the whole process and requires a whole lot more admin outside of xero... I know you can do it through the non-app 2-step route, but not this way...