How to send repeated reminder emails

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“Not this again….”

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May 18, 2021

It’s Groundhog Day…again…

One of my favourite all time films is Groundhog Day. Maybe I’m a sucker for romantic comedies, or for the power of transformation…or maybe it’s just because Bill Murray is a comedy god! Whatever it is, I’ve watched the film too many times to count and my wife hates whenever we watch it as I’m forever saying the lines before they are actually used.

The concept is a simple one – someone reliving the same day over and over again (if you like that type of stuff, check out “Palm Springs” and “Edge of Tomorrow” both follow the same principle). Life fully “on repeat”.

Unlike these films however, setting up stuff to repeat constantly isn’t necessarily something to dread – we’ve all got those tasks that need to be done each week that keep the wheels turning in our businesses and ensure they move forward – and some of them might even involve your leads or customers.

We love a Mailchimp challenge

Sending repeated reminder emails to lots of people is actually not that easy to achieve in many systems. I’ve used several CRMs (Customer Relationship Management) and although you can set reminders for individuals, it’s hard to do it for groups of people, let alone send them an email every week/month.

And, up until recently, it was almost impossible to do it with Mailchimp…but here at Chimp Answers we like a challenge and so we spent a bit of time playing around with Mailchimp to work out how you can set up a repeating email that can be sent the same time each day/week/month.

Here are some circumstances you might need to use a repeating email for:
  • You need to send monthly reminders to people about a regular event/session they need to attend.
  • You need to send weekly reminders to ensure that key people attend an update meeting, or send you information – for example a client of ours needed to send reminder emails to all of their clients to receive updates from them on their movements for the week…
  • You might want to send quarterly reminders linked to an RSS feed with all your latest blog posts in.

In the past you could send “triggered” emails which connect to an RSS feed and then send whenever the blog is updated…but what happens if you just want to send a 28 day digest of things…but pull in the last 3 blog posts?

If you want to send a regular email that goes out on a specific time gap, then check out this video which explains how you can do it yourself using Mailchimp Customer Journeys (you’ll need to be on a Standard or Essentials plan to do this).

The fact is, Mailchimp isn’t really designed or optimised to do this type of thing, but that doesn’t mean you can’t use it to do it.

Just remember – the email WILL be the same each time, unless you use things like RSS or Merge Tags to make the text a bit varied each time.

If you’re not sure whether this will help, follow the steps in the video and test it yourself – and start thinking of all the circumstances where you might be able to benefit from the ability to repeatedly send emails over a period of time.

It’s like your Mailchimp Account having it’s own little Groundhog Day!

Robin Adams

Robin Adams

Robin Adams is a business owner who is passionate about helping businesses build effective marketing systems that work and don't waste money. Having a lifetime of Marketing experience (he's got a degree in Marketing before there were degrees in Marketing!) and having worked for big and small businesses and both client and agency side, he understands not only the theory, but the systems that are required to underpin everything.
51% marketer and 49% Chimp, Robin is the main man behind and the Mailchimp Answers Facebook Group - the world's biggest Mailchimp User Group. Connect with him on Linkedin.


  1. Helen Hares

    I take it this will not work with old automations, only on new journeys?

    • Robin Adams

      Helen, thanks for the comment – I’ve not tried it with old automations… they could work in the same way…

  2. Craig

    I wish I’d found this before I banged my head on the stupid monkey wall for a month. My last attempt was as you explained (remove then add the same tag inside the automation).

    Thanks so much for making sense of–and helping overcome–one of Mailchimp’s most glaring drawbacks.

  3. Chris Bell

    Thanks for the jumping off point! This is good information. I was racking my brain about how to set up upcoming payment reminders for my subscribers who pay with PayPal. Stripe has built-in payment reminders for the debit/credit customers, but PayPal does not. I wanted to have some kind of recurring email that goes out a week before the payment to remind them.

    In order to accomplish that for me, I had to take your approach, but add a third one-way loop to the mix. This is because the first reminder will happen only about 3 weeks after they join, but every reminder after that should be on a monthly schedule. Instead of a loop, I’ll call it an on-ramp, because it’s only used once. It starts when a new member subscribes with PayPal, they are given a “PayPal Initial” tag. They start the journey and there is a 23 day delay. Then the “PayPal Initial” tag is removed, and the “PayPal A” tag is added. At this point they enter the loop you describe in the video.

    Oh, the other thing I added was If/Then Splits. Obviously if someone cancels their membership during a billing cycle, I don’t want them receiving an erroneous email stating that we are about to charge them again. So in each loop of the cycle, I added an If/Then Split. If the contact is still tagged “Current Member” then they continue on in the loop. If not, then they exit the journey, and therefore the whole cycle.

    Thanks again!

    Founder – Scale Speed Garage


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