Hi @CC_ArdMoor 

Thank you for posting your question in the community. 

With a winback flow your goal is to try and get a lapsed or even possibly a churning customer to give your business another chance and make another purchase. Depending on your product/service, it might make sense to send another winback email after a purchase if the purpose of the product is meant to be replenished relatively often. 

One thing to keep in mind is when customers catch on to discount flows and they start gaming the system to only purchase when they know they will get an offer/discount. But again, if your product replenishment rate suggests that a 4-month window after a purchase denotes a lapsing customer and you have an enticing offer to keep them coming back, I don’t think it hurts.

But, you could also set additional logic on the flow to only allow users into the flow once every 6 months, or only receive the email twice. 

I do think if its likely your customers could receive the winback email more than twice, it does make sense to schedule refreshing the email/offer/messaging once or twice a year and differentiating the offer. Both of those will help keep customers from seeing the same email/offer but might also keep them more engaged.

You could also think about sending a softer winback email without a discount earlier after their last purchase. These email can be effective in showcasing new products, highlight social proof (testimonials), or asking for feedback on how you are doing to meet their needs.

I hope this helps!

@In the Inbox