Founders are falling out of love with Postmark, a popular transactional email service

Transactional email service Postmark has long been a stalwart of the indie hacker starter pack. It offers a special package for bootstrappers and even brands itself as "the best email provider for bootstrapped startups."

But after a series of recent missteps — including a near-10-hour outage over an expired SSL certificate — founders have started to question the company. Are grumblings in Telegram chats and rants on social media signs that founders are falling out of love with Postmark? That's what experiences bootstrappers have shared with me suggest.

Launched by small startup Wildbit in 2009, Postmark lets businesses automatically respond to customer actions via email. Think sign up confirmations, password resets and delivery updates.

It's since grown its platform and now offers everything from notifications by webhook to analytics.

Postmark grew so valuable that in 2022, mega marketing service company ActiveCampaign snapped it up and brought the Wildbit team under its umbrella. For the most part, it seemed to retain its favor among indie hackers after the sale.

In January, superstar indie hacker Pieter Levels waxed lyrical about Postmark on Twitter (now X), having just switched over from rival SendGrid.

"I love everything about Postmark," he wrote, praising the sign up process, login, design, and interface. "It all works so well."

But a few months down the line and things weren't quite so rosy.

Nearly 10 hours of downtime

In September, a crucial Postmark service went down for nearly 10 hours. Emails that used the company's Simple Mail Transfer Protocol (STMP) service simply weren't sent.

The reason? An expired SSL certificate.

This file verifies the identity of a website and facilitates encryption. You can tell a website has one if it uses the "https" URL prefix. It's a basic but fundamental part of any online security set-up.

According to its service logs, Postmark's service went down when an SSL certificate expired at 7 p.m. EDT on September 15. An engineer saw an alert a few minutes later, but thought it was a false alarm.

It went unactioned until other engineers noticed the issue at around 1 a.m. It took them until 4.02 to identify the problem and almost another hour and 45 minutes to fix it.

After the incident, Postmark said it was performing "An audit of all certificates... to ensure automatic renewal."

But for may indie hackers, this simply wasn't enough.

Some founders blamed the outage on Postmark's 2022 acquisition and pledged to leave the service, questioning how much of its original team was even still in place.

Fathom Analytics founder Jack Ellis said he was moving his company off the service, writing on X:

"Postmark was acquired two years ago by ActiveCampaign, a company with ~1000 employees. The only changes I've seen since then are price hikes, extra cost for adjusted email retention period & now an SMTP SSL certificate expiring. What's your favourite change that they've made?"

In a comment he said the situation was "so unbelievably sad because ex-ownership was solid and they had built a beautiful product."

More bad press

A few weeks later, Pieter leveled another blow on the service, posting an image of a malicious link block message from Microsoft Defender to X.

If you use Postmark, he claimed, "Microsoft Office now classifies your links as malicious."

The issue, he claimed, was that Postmark wasn't keeping its email links clean enough to get through Microsoft's security measures.

Postmark disagrees with the Nomads founder. A spokesperson told me the issue didn't affect everyone using its service.

"We confirmed that it was isolated to the customer. Postmark’s link tracking does not generally cause a link to be classified as malicious, and we were unable to replicate his issue," a spokesperson said.

"That said, when algorithms change in products like Microsoft Defender, sometimes legitimate services offering transactional email delivery, domain click-tracking, or link shortening may get temporarily flagged."

Nonetheless, founders keep getting hit with bugs — some of which are critical.

Five days' wait for a critical fix

Razvan Ilin's Notion-to-newsletter platform Notocat relies on Postmark for pretty much everything. "Custom domains, metrics, tracking, senders, broadcasting emails," he told me.

Just before Thanksgiving, his app became unusable. The company had mistakenly deactivated his account without any warning.

It took five days for Postmark's customer support to get back to him and confirm he had done nothing wrong — a period during which Razvan, who also runs Chartbrew, simply considered giving up.

When a customer service agent finally responded on December 3, they promised they'd reactivate his account. But they didn't.

It took another frantic email and several more hours to get Razvan's account going again. And even then, he still couldn't access parts of the API.

Dissatisfied as he was with the response, Razvan told me it would take "a lot of work" to switch to another provider because Notocat is so deeply integrated with Postmark. His own users would need to change their domain settings to continue using his product.

Postmark didn't respond when I sent follow-up questions about Razvan's experience. But a spokesperson insisted the "growing" service was still a great option for indie hackers.

The firm was "committed to supporting the community of bootstrapped companies," they said, adding that "it offers rewards to those who have achieved revenue traction without external investment, helping them grow sustainably while managing email expenses."

Do you know anything else about changes at Postmark? Have you experienced issues with the service? I would love to hear from you. Send me an email at [email protected].