Ask Ada: Why Aren’t Emails From Tryst Reaching my Inbox?

Ever been waiting by your inbox for an email to arrive and it doesn't? No trace of it in the spam folder either, so what gives? Where did the email go?  You may have just encountered the unfortunately common practice of silent delivery failure.

Email might seem simple at face value - send a message to user @ thisserver.com, but thanks to an unholy amount of spam, mail servers have rules that decide if that message should end up arriving in a user's precious inbox. We all hate spam so it makes sense we have these rules in place to avoid the obvious stuff not getting through, but things get frustrating when a message is on the fringes of what the mail server operator thinks is spam.

There's a plethora of conditions a mail server checks against incoming email before allowing it through. Common ones include:

• Does the email come from an address flagged for sending spam in the past
• Have other users of the same email server reported issues with this sender or the sending mail server?
• Do recipients of this email open them or send them to the trash right away?
• Does the email allow users to unsubscribe easily?
• Are there "trigger" words in the subject or body?
• Is the sender on any other spam lists?
• Plus many more that are not made public.

These non-public rules are what damage legitimate email senders like Tryst, which already struggles due to being adult content which spam filters are aggressively biased towards deleting. Most incoming mail servers are polite enough to respond with a reason why a message was denied, so the administrator (ie. Tryst) of the sending server can try again. Unfortunately, the biggest mail servers in the world - Google's Gmail and Microsoft's Outlook - don't do this.

With Microsoft in particular, it's a guessing game as to why an email doesn't reach an inbox or a spam folder as they simply respond with a vague error message and no information for a server administrator to act on. These companies are so massive that it's virtually impossible to reach a human for support and if you do, they often don't know why an email didn't arrive as their spam filters are automated systems that few people have access to.

Some providers, primarily ISP provided email addresses, have built-in, enabled by default, "family" and "child" filters that reject any email alluding to sex and sex work. These filters often delete the message prior to reaching an inbox or spam folder. So if they're in operation and a message is blocked, you wouldn't even know it was happening.

As much as we need spam filters to protect us from the deluge of junk that would inundate our inboxes without them, sometimes those spam filters go too far and there's often nothing anybody can do about it. It sucks, but that's the state of the internet in 2023.

Not all hope is lost. Here's a few tips that can help improve email deliverability from businesses like Tryst. None of them are foolproof but every little bit helps:

• Add "hello@tryst.link" as a contact in your email platform's contact list. Here’s instructions on how to do that.
• Open emails from Tryst instead of deleting them right away.
• Disable any "family" or "content safe" filters your email provider may have turned on by default.
• If you don't want emails from Tryst, unsubscribe instead of marking it as spam.
• Use an email provider such as Fastmail, Hushmail or Proton, that do not silently reject legitimate emails.

Got a tech question for Ada? She wants to hear from you!

Ada answers all your questions about tech, the online world, and staying safe in it. No question is too silly, no hypothetical is too far-fetched! Learn to leverage devices, systems, and platforms to your benefit.