Windward Software long-term review - the good and bad

⭐ Review Discussion 👁️ 2,968 views 💬 15 replies 📅 Oct 16, 2025

Hey everyone,

Windward Software long-term review - the good and bad

I'm running a grocery store in San Jose, CA and looking for advice. We currently have been looking at different options. Any recommendations or experiences to share?

Thanks in advance!

Amanda Scott 👑 Master

1,245 points • Member since Jun 2025

💬 15 Replies

Eric Coleman

👑 Master

219 posts

Oct 26, 2025

Different perspective here - you might want to consider a different approach

👍 Helpful (13) 🔗 Share

James Mitchell

👑 Master

221 posts

Nov 4, 2025

This is why we switched to Thrive POS. No regrets.

👍 Helpful (4) 🔗 Share

Frances Russell

👑 Master

212 posts

Nov 6, 2025

I've been using Auto-Star for 7 months and it has been working well for us

👍 Helpful (4) 🔗 Share

Nancy Sanders

👑 Master

217 posts

Nov 7, 2025

Great question! In my experience with Clover Dining, it has been working well for us

👍 Helpful (0) 🔗 Share

Jerry Stewart

👑 Master

218 posts

Nov 9, 2025

Check out the scale integration setting, that might help.

👍 Helpful (5) 🔗 Share

James Sanders

👑 Master

218 posts

Nov 11, 2025

Agreed with the above. Also worth mentioning you should also check the settings

👍 Helpful (20) 🔗 Share

Carlos Hughes

👑 Master

235 posts

Nov 12, 2025

Check out the produce lookup setting, that might help.

👍 Helpful (6) 🔗 Share

Nancy Rogers

👑 Master

225 posts

Nov 12, 2025

Make sure you're on the latest version. That fixed it for us.

👍 Helpful (2) 🔗 Share

Karen Johnson

👑 Master

234 posts

Nov 13, 2025

We had the same issue. What worked for us was restarting the terminal

👍 Helpful (2) 🔗 Share

David Wright

👑 Master

198 posts

Nov 20, 2025

The WIC/EBT support is definitely worth the extra cost IMO.

👍 Helpful (20) 🔗 Share

Megan Foster

👑 Master

195 posts

Nov 20, 2025

Had the same problem, support was very helpful when I contacted them.

👍 Helpful (6) 🔗 Share

Raymond Chen

👑 Master

191 posts

Nov 20, 2025

Just went through this. Here's what I learned: take your time with the setup

👍 Helpful (12) 🔗 Share

Brenda Lewis

👑 Master

199 posts

Nov 22, 2025

Cost us about $80/month all in. Worth it.

👍 Helpful (5) 🔗 Share

Frances Russell

👑 Master

212 posts

Nov 28, 2025

Just went through this. Here's what I learned: take your time with the setup

👍 Helpful (2) 🔗 Share

Eugene Bennett

👑 Master

205 posts

Nov 28, 2025

Check out the scale integration setting, that might help.

👍 Helpful (17) 🔗 Share

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