I Switched to ProtonMail, then Switched Back to Skiff

Recently, I migrated Fifthdread.com from my web-hosting provider to self-hosting. During this switch, I had to decide on an email provider for the many Fifthdread.com email addresses. There are a vast amount of email providers out in the wild, so I had an uphill battle to find the best provider for my custom domain's email. That's where a ton of research was required in order to select the best choice for my needs.

Proton Mail is often recommended by the privacy focused communities online, but I decided to use a newcomer in the space, Skiff, for email services. Skiff has been growing a reputation as a great value option in the privacy focused email space, and for good reason. They offer many of the same services that larger providers provide, at a fraction of the price. With that being said, I had a big problem with Skiff. They don't support SMTP access.

Not supporting SMTP is painful for me for a big reason. I self-host many platforms such as NextCloud, Portainer, Proxmox, Uptime Kuma, etc. All of these platforms share one thing in common: They want to send emails. Notifications, password reset verification emails, whatever. Previously, it was trivial to have them send an email from one of the various Fifthdread.com email addresses- often, it was noreply @ fifthdread.com. However, because Skiff doesn't support SMTP, it is impossible for me to route that traffic through Skiff.

What does that mean in practical terms?

The long story short, it means all my Fifthdread.com email will be flagged as spam- at least the emails coming directly from my servers.

Let me explain how things work in the quickest way possible. Let's say you have a Gmail account. When you receive an email, Google checks to see if that email comes from a trusted sender. This is to combat spam bots from impersonating you. For example, if my server sends an email to your Gmail from noreply @ fifthdread.com, it'll check (via DNS) if my server is trusted to send fifthdread.com emails.

Here is the problem. The only one currently trusted to send Fifthdread.com emails is Skiff. So emails coming directly from my server? They get flagged as spam, or maybe dropped completely.

Obviously that's a problem. However, it normally has an easy solution: Configure an SMTP server. If I sent all my traffic through my email provider, who would then send the email on my behalf, than it wouldn't be flagged as spam. This is something I used to be able to do with my old email provider, and is something you can do with Gmail or similar services. Check out this graphic on how it would look.

Here's the problem. Skiff doesn't allow SMTP to go through their service at this time. This means I am unable to send traffic from my server to route through Skiff, meaning that my emails are forever to be flagged as spam if they send emails directly to the recipients. Not only that, but many of them don't allow direct-sending. Some require an SMTP server to be configured in order to send emails at all. This is a problem.

Is ProtonMail the Solution?

It seemed so, at first. Everything I read seemed to support that ProtonMail supported SMTP- I mean just look at this breakdown they publish below! They say that Mail Plus subscription comes with SMTP, but that comes with a big *.

With the full intent to switch to Proton Mail, I made an account and subscribed to the Mail Plus monthly subscription in order to test the SMTP functionality. However, I found that full SMTP support is reserved for the Business Subscription ONLY- at a large premium over the "individual" plan. Individuals can only use their "bridge" desktop application to interface with mail clients like Outlook or Thunderbird. You are unable to create an SMTP Token without a Business Plan.

Discusting. For the privilege of being able to route my emails through Proton Mail, I'd have to pay over $120 a year. That's a huge ask, considering that I'm paying Skiff significantly less, at $36 a year. There's no way that I'm willing to pay that premium to send out some simple emails.

The way I see it, I have two options. Either I send emails through mailgun, which I setup to send bulk-emails to my subscribers for Fifthdread.com, or I just use my Gmail SMTP address. That means I'd configure my servers to send emails as Fifthdread@gmail.com. Gross.

Mailgun is an option, but it's not a typical free solution. It's something that has limits. After a certain amount of traffic, I will be charged for the privilege to use mailgun. And my email would come from noreply @ mg.fifthdread.com... Neither solution is great.

Proton Mail is limiting

ProtonMail also doesn't allow Mail Plus users to setup other user accounts. With Skiff, I can provision other email addresses for friends and family- as far as I'm aware, there is no limit. Proton Mail think they can charge for this however, and you'll not only have to pay for a business package, but you have to pay PER USER. That's right. Each user that receives an email? That's increasing your cost by $12 per user. Absolutely discusting. Skiff just give that to you. Also, you're very limited in how many email addresses you can make.

What did we Learn?

That my web-hosted mail server was more capable than I thought. The fact that I had SMTP capability previously, and these other providers either don't offer it, or offer it at a cost premium- that's insanity. Of course, I was paying a high price for it previously. The real question is weither or not SMTP access is worth the extra price, and the answer is a large NO. I look forward to the day that Skiff offers SMTP access, but in the meantime I'll just route through Gmail or accept that my emails hit the spam box.