Hello @thebrandrich,
Thank you for sharing the logs ahead!
Could you please navigate to WooCommerce → Settings → Square and make sure the inventory sync is enabled?

Link to image: https://d.pr/i/Hhm5Xb
To get a better understanding of how the sync process works, please take a quick look at this guide: https://woocommerce.com/document/woocommerce-square/sync-settings/
Look forward to hearing back from you.
My view looks a little different but yes it is enabled. We have woocommerce as the system of record and Enable to push inventory changes to Square
Hi I’ve setup Woocommerce and connected it with Square. The initial and following (both automated and manual) synchs do not correctly match the quantity for products from Woo.
The stock is synced by matching SKUs so please make sure you’re testing with products using the same SKUs.
Also, it might be worth trying to increase your server’s PHP Time Limit.
Just to clarify, the PHP Time Limit is the maximum amount of time that PHP scripts are allowed to run. If any script runs longer than the set time, PHP will stop it and flag an error. For sync tasks, this can often be a limiting factor. You can adjust this by tweaking the max_execution_time in your PHP configuration file. Your hosting provider should be able to help you with this.
Once you update it, navigate to WooCommerce → Settings → Square → Update and try manually syncing products.

Link to image: https://d.pr/i/aH5Z67
Let us know how it goes!