Sgt_BilkoPerhaps e-junkie could even send out an automated link to the buyer telling them that they will receive an email later from the seller with a link that first needs to be manually authorised. We could then take the automated download link we receive and use it to craft an email by hand to the buyer. In this instance we are sending a link because the book is physically too large to email.
My previous reply explains how to bypass redirecting buyers to a download page after checkout, how to suppress automatically sending buyers a link to that page and instead send them a custom message advising them to await a file or link to be provided manually later, and how you can obtain that file or link.
I will also ask Development to consider adding a thank-you/download page link to the standard Sale Notification email we send sellers for each order, so sellers could simply copy and paste that link into a personal email to the buyer.
Can we see room to make this work so that it is as simple as possible yet stays within the rules? I would argue that I just about manage this already because the customer receives a link rather than an automated download. It's not a case of buy now and download immediately afterwards as described by HMRC.
I think we can make this work with a bit of ingenuity and it would be better for all concerned.
It's not technically possible to make any user's computer spontaneously download a file without any interaction from them -- indeed, if any such method were found, it would be deemed a bug and a potential security risk, as it would certainly be exploited by hackers, malware distributors, and other such crooks -- so that can't possibly be what HMRC means by automated supply. At least some nominal user interaction, such as clicking a link or button, must be required for the user to specifically request and initiate a download, so that nominal interaction cannot be taken to mean the download is not automated.
In typical operation, following checkout buyers can normally access a thank-you page we automatically generate with their download link(s), and we email them a link to reach that page as well. IMO, this is certainly an automated supply as HMRC describes; arguably, manually emailing the buyer a link to access that download page might count as automated supply as well. Note in particular their example, "Link to online content or download sent by manual e-mail", is explicitly noted as an electronically-supplied e-service; by that example, manually emailing your buyers a link to their E-junkie thank-you/download page would not appear to exempt you from the rule change.
We aren't tax attorneys or accountants, so take with a grain of salt any regulatory interpretations we may offer, but it seems like you may be splitting hairs trying to find a loophole in the letter of the law to avoid complying with the intended spirit of the law. As such, you might consider whether you're willing to incur the potential legal expense and hassle of defending your case, not to mention penalties if you lose, if HMRC ultimately disagrees with your interpretation.
The page you linked from HMRC, including the section you quoted within its broader context, seems to be making the case that the mere act of providing a file to a paying client via the Internet does does not inherently subject that business relationship to the new VAT rule on electronically-supplied e-services -- e.g., if you're a paid consultant and happen to provide files to clientele in the course of your consultation, or if you're a designer or programmer and provide files your clientele have paid you to create for them, those transactions are not subject to the rule change.
However, if you're providing files as pre-prepared retail commodity products at a large enough scale that would make delivering each file individually by personal email impractical, then any form of automation you may adopt to make providing those files easier would put you further away from the "manually supplied" case and more towards the "electronically supplied" case that's subject to the rule change.