Captain's Log: Stardate 79603

I mentioned in my last post that I've begun working on a marketing plan for Anukari. I'm feeling pretty optimistic that it will be possible to get a steady trickle of sales going, and I also think it's possible that something more than a trickle could happen at some point. Fundamentally I just want enough sales to fund my continued development of Anukari, but I'd obviously be open to more sales, which could lead to further interesting possibilities.

Either way, I like to plan for success, and so one thing I've been working on is fixing a few small customer support headaches, so that they don't become big headaches in the event of lots of sales.

Long term the biggest thing will always be making sure Anukari performs well and is compatible with as many machines as possible. That is feeling pretty good right now.

Now that the product is not generating so many support requests, the next biggest support issue is with account emails failing to be delivered to users. The chief issue here is that occasionally a user won't receive the email containing their license key after they purchase Anukari.

This is immensely frustrating for the customer. The normal flow is that when they checkout via Shopify, they will receive a receipt from Shopify, and in that email, it says "you'll get a second email with the license key." Obviously I'd prefer for these to be one email, but that's not really possible at this point, and it's not that big of a deal.

But some users get the email from Shopify, and then never get the second email. I am the only customer support person, so this means that if someone buys Anukari right after I got to bed, even if they email to complain, they won't get their license key for at least 8 hours. Awful! Imagine it's Friday night, you're stoked to finally have a few hours to play with some new VSTs, you spend your hard-earned money on one, and then no license key comes until tomorrow. Ugh. I'd be super annoyed. (That said, evidently my customers are saints, because they have all been super understanding.)

Email is a tricky thing. Spam filters exist, and also things like IP reputation are really complicated. I have worked on spam/fraud prevention, so I know how difficult some of these problems are.

When email delivery fails, my first question has always been "did you check your spam folder." Curiously, this has almost never been the case.

The main reason that I've had emails fail to be delivered is that Resend, my email provider, simply chose not to send the emails as requested, due to their global email suppression list. This is a list of email addresses spanning across all Resend accounts, that have hard-bounced or been flagged by providers. If a customer's email somehow ends up on this list, Resend will simply not attempt any email delivery. Resend's help page says that a user marking an email as spam could be a reason for them to be globally suppressed. That means that if another Resend user sends a spammy-email to someone, it might block you from sending email to them later.

I've contacted Resend support about this several times. At one point I was told that I could remove addresses from this global suppression list myself. At other times, the Resend customer support folks had to remove the email address for me. The GUI for suppression seems to have changed a couple times, right now it doesn't look like Resend users can actually request removal from the suppression list. In my case, the GUI stated that the email address that failed delivery had already been removed from the suppression list; however I retried sending the email and it was suppressed again.

Over the course of several contacts with Resend support about this global suppression list, it became clear that Resend sees this as a feature, not a bug. And again, I understand that they have a difficult problem to solve, maintaining good deliverability with multiple users, some of which surely are spammers trying to abuse Resend's platform.

The thing is: to me, Resend has exactly one job, and it is to attempt deliver email when I send it. And sometimes, Resend simply chooses not to even attempt delivery. On purpose.

The email addresses that Resend has suppressed are totally normal, just everyday people, typically on GMail accounts, nothing weird. Shopify's emails invariably get delivered without issue, and then my emails from GMail to respond to their support requests also work perfectly. Perhaps there was a one-time delivery hiccup, or another Resend user sent out some spam. Either way, Resend is being super aggressive about suppression in a way that impacts all their users.

IMO the global suppression list is an incredibly bad design, especially with how heavy-handed Resend is being in populating it. I can verify firsthand that it causes plenty of grief. It's a difficult problem, but there are many approaches to managing reputation for shared email IPs. This one is no bueno.

So after several complaints to Resend without a solution, I migrated anukari.com completely off Resend, to Postmark. Postmark has a very good reputation for high deliverability, which again, is the only thing I actually want from an email provider. As far as I can tell, Postmark does not have a global email suppression list, but instead has per-account per-stream lists, which makes way more sense. Here's hoping that this leads to fewer frustrated customers!