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Windward Software long-term review - the good and bad

⭐ Review Discussion 👁️ 5,191 views 💬 10 replies 📅 Nov 11, 2025
Sharing my experience in case it helps others.

We recently made some changes to our setup

Has anyone else seen this?
Chris Wood 👑 Master
1,495 points • Member since Jun 2025

💬 10 Replies

Kevin Robinson
👑 Master
214 posts
Nov 11, 2025
Check out the retail integration setting, that might help.
Dorothy Scott
👑 Master
195 posts
Nov 12, 2025
We had the same issue. What worked for us was contacting support
Peter Stewart
👑 Master
228 posts
Nov 15, 2025
Had the same problem, support was excellent when I contacted them.
Brenda Park
👑 Master
231 posts
Nov 15, 2025
Check out the waitlist feature setting, that might help.
Carlos Jenkins
👑 Master
257 posts
Nov 16, 2025
Great question! In my experience with Square POS, it has been working well for us
Rebecca Perry
👑 Master
223 posts
Nov 18, 2025
+1 to this. We've seen similar results.
Sandra Taylor
👑 Master
237 posts
Nov 19, 2025
Agreed with the above. Also worth mentioning you should also check the settings
Scott Anderson
👑 Master
205 posts
Nov 25, 2025
This is why we switched to QuickBooks POS. No regrets.
Michelle Reed
👑 Master
251 posts
Nov 25, 2025
Great question! In my experience with Payanywhere, it has been working well for us
Lauren Butler
👑 Master
233 posts
Nov 28, 2025
This is why we switched to Homebase. No regrets.

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