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Hacking auto-responders for fun and profit

Are you wondering if your email campaigns are in the spam folder?

My worst nightmare isn’t that my emails aren’t being opened (have you ever read my email subjects?) My absolute worst nightmare as a marketer is my emails are ending up in the spam folder.

There are some really awesome (free) tools to check if your domain is healthy, and what the deliverability of your emails are. But I always have a sneaking suspicion these tools aren’t 100% accurate.

Now to the “hack”

Schedule an email to go to a decent sized segment of your email list. I would say minimum of 100 people to get a good sample size.

Now this is going to go against everything in your soul, trust me it hurt for me to do it too. Schedule the email to be delivered on a national holiday like Christmas, or New Years day.

auto-reply soul crushing pain

Don’t send a holiday email(those are the worst), treat it like it’s part of a normal campaign. Just in case someone actually opens it.

Where is the hack? The hack is testing your deliverability and if your emails are going to spam.

If they are going to spam the auto-responder is likely to still respond. And TELL you it’s in spam!

are your emails going in the spam folder

Oh no, I’m in the spam folder!

Don’t despair, it happens to us all eventually. If you’re seeing less than 5% in the spam folder as responses, don’t sweat it. Here’s a few tips I try to stick to when setting up email campaigns.

  1. Check your subject lines!
  2. Don’t send HTML emails!
  3. Keep your emails short, sweet.
  4. Don’t send HTML emails, text only!
  5. Use a service like mailshake that actually sends through your g-suite account. If you’re using an email service like active campaign, or mailchimp make sure you verify your domain.


The bonus effect of this test, from everything I can tell an auto-reply is treated by exchange and even gmail(g-suite) as a response, increasing the likeliness your email will go to the inbox the next few emails you send.

We’ll talk about that theory in a post later.