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Question

Session-based triggers – do they work with smart files?

  • September 2, 2025
  • 6 replies
  • 26 views

The Enloe Creative

Hey wonderful community. I am struggling with a number of my 2.0 automations not working as they should. The chatbot has explained to me that if a client schedules a session using a smart file or lead form, that session-based triggers will not work within an automation. Is this true? 

Example – I send my automatic Family Session Booking File. They schedule a session and pay me. I have an automation that says, “10 days before family sessions start, send email X.” Is that a no go?

 

Thanks!

6 replies

Alicia Bauer
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  • Newcomer
  • September 3, 2025

@The Enloe Creative - Hey there! Great question, and yes, what the chatbot told you is unfortunately true (for now).

When a client schedules a session within a Smart File or through a lead form, that session date doesn’t connect to the automation’s session-based triggers like “10 days before session start.” Currently, those triggers only work if the session is scheduled through the scheduler tool that's directly embedded in an automation step—not inside a Smart File.

So in your example, even though your client scheduled and paid via the Smart File, the automation won’t recognize that session date to trigger the "10 days before" email.

This is a known limitation, and many of us have run into the same thing. A workaround right now is to manually trigger the next step or use project date-based triggers instead (if that makes sense for your workflow).

I’d also encourage you to submit a Feature Request or find the existing thread and upvote it—this is a popular ask, and the more voices behind it, the better!


The Enloe Creative

@Alicia Bauer one more question – you mentioned directly embedding a scheduling in an automation. How do I do that? I can’t quite figure out what you mean!? Thanks


Alyssa Nance
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  • Newcomer
  • September 10, 2025

@The Enloe Creative I’m assuming she means if you’ve added the scheduler link into an email that is sent in your automation. That is the only other way I know of to be able to share a scheduler link at this time.


The Enloe Creative

Thanks ​@Alyssa Nance. This seems like a real roadblock after Honeybook has pushed smart files with service selection + booking. That’s what I use exclusively these days. Anyway, I appreciate your feedback!


Alicia Bauer
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  • Newcomer
  • September 12, 2025

@The Enloe Creative - I understand the frustration and I agree with you it is a roadblock. I know it isn’t ideal but please be sure to reach out to support and/or leave a feature request so the HB team knows the struggle and can take it into consideration for updates. 


Alyssa Nance
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  • Newcomer
  • September 12, 2025

@The Enloe Creative Yes, a huge roadblock that is highly confusing. I’ve had to make this super clear to a couple of my clients recently, because they couldn’t figure out what they were doing wrong with their automations. 

I’ll look if there’s already a feature request for this and can link it here for all of us to upvote (they really are listening to what we’re voting on). This may also be in the works for something they include as they continue to improve the new builder, anyways. There’s already been several things added over the last few months that were severely lacking from the first couple iterations.