thread Re: Best way for add on/session enhancements for online booking in Appointments & Bookings

Best way for add on/session enhancements for online booking

MMakris — Thu, 23 Jul 2026 18:09:53 GMT

Hi all,

I own a very busy massage practice. The vast majority of my clients book online. Other online booking systems that focus on massage have a screen that pops up after a client books a session asking if they want to add additional services (like a foot scrub, hot towel wrap, hot stones, etc).

In the past I’ve enabled clients to book multiple services, but enough of them messed things up where I had to quickly turn that feature back off.

I want to have a streamlined menu (for a clean look), but I hate leaving money on the table as clients will book these add-ons when given a choice.

What I would love is a client books a particular session length and then a drop down pops up with the variations available. I’ve tried doing the variations already but it shows them all on one loooong list that looks cluttered and does not fit my high-end brand.

So please help! What is the best way to do this? Or is Square just not able to handle this yet? Seems lately they’re focusing more on food service.

Thanks for any recommendations. Also, I don’t want to create a bunch of extra manual work for my staff. I know I might be asking for too much here.

Although if I’m leaving a bunch of money on the table, Square is too by not providing me a clean way to add service upgrades.

Thanks,

Melissa

Re: Best way for add on/session enhancements for online booking

kacey_k — Sat, 25 Jul 2026 00:19:54 GMT

Hi Melissa,

I completely understand what you’re trying to accomplish. A guided add-on flow after a client selects their primary service would create a much cleaner booking experience than displaying every possible variation in one long list.

At this time, I don’t believe Square Appointments supports a post-booking upsell or add-on selection screen like some massage-specific scheduling platforms. The closest options today are creating service variations or allowing clients to book multiple services, but as you’ve experienced, those approaches aren’t always ideal for businesses with a curated, high-end booking experience.

I think this would make an excellent feature request. A simple “Would you like to enhance your appointment?” step with optional add-ons would help businesses increase revenue while keeping the booking flow clean and easy for clients.

In the meantime, one workaround some sellers use is keeping the online booking menu streamlined and offering upgrades through appointment confirmations, reminder messages, or during check-in. It’s not as seamless as an integrated booking flow, but it can still encourage add-on sales without cluttering the service menu.

Hopefully the Product team sees the value in this. I can definitely see how it would benefit service-based businesses well beyond massage practices.

Re: Best way for add on/session enhancements for online booking

MMakris — Sat, 25 Jul 2026 19:51:08 GMT

Thanks, Kacey, for confirming my suspicions. I wanted to make sure I wasn’t missing anything!

Yes, lots of businesses do upselling, so many would stand to benefit. I love that Square keeps making improvements, and overall I’ve been quite happy with them these past eleven years. Hopefully sometime soon this feature will be available. It is badly needed.

Re: Best way for add on/session enhancements for online booking

TCSlaguna — Mon, 27 Jul 2026 15:24:14 GMT

I love the idea of an add-on flow. I would put it on the Feature Requests page so it can get kudos and catch the eyes of the team to work on.

Along the same lines as you, we have clients who go over on appointments. It would be nice to be able to streamline how these are done. I know one limitation is their card would have to be on file.

Re: Best way for add on/session enhancements for online booking

Getonthebus — Mon, 27 Jul 2026 19:16:41 GMT

Beautiful suggestions from @kacey_k here. The “Would you like to enhance your appointment?” would allow you to circle back around to your list of services/add-ons for additional purchase. And your reservation confirmation could make several suggestions for add-ons as well.

Re: Best way for add on/session enhancements for online booking

Doran — Tue, 28 Jul 2026 23:29:01 GMT

The way I work around the add-on is to use variations. So my Hydrafacial is Hydrafacial or Hydrafacial with booster or Hydrafacial with perk, etc. It is one drop-down menu under Hydrafacial. It is "cleaner" but you have to go in and do it for all of your services so a bit of work up front.

Re: Best way for add on/session enhancements for online booking

mitin — Wed, 29 Jul 2026 20:32:54 GMT

HI @MMakris That is a limitation on the square site.
If you can share your booking link, I would love to take a quick look.
I resolved all of my booking frustrations by just using custom website and booking flow.
It started with the pain of analytics but then got involved into customizing it for my business need etc and controlling the user experience to what worked best for me vs using square online.
Upselling and recommendations are great add-ons and help the bottom line

Re: Best way for add on/session enhancements for online booking

MMakris — Thu, 30 Jul 2026 01:33:20 GMT

Thanks, but I’m just going with the variations. It’s not ideal, but workable for now. I just wish Square would offer this feature.

Also, I thought the modifiers would work, but after I put them all I realized they don’t work with services. 😞

Re: Best way for add on/session enhancements for online booking

CurlyDoodle — Sat, 01 Aug 2026 13:38:02 GMT

I made a decision in my business to keep it simple and not line-item add-ons. So, another possibility for you is to create packages like "one hour massage with hot stones, etc." That way you only have a few options like basic, midlevel, and deluxe, rather than having the client choose multiple add-ons. Roll the additional services into one price.