Unexpected system changes are made, how to know and stay ahead of it?

[fireworksking]

I have seen an issue with new features effecting the way my business functions.  A change was made to the way categories behave (more than 1 category per item is now allowed) and we calculate discounts based on category, which led to discounts being calculated not only wrong, but inconsistently.   The issue was very strange and difficult to detect.   I had dozens of customers charged in correctly due to a bug caused by an unannounced system change.

Support acknowledges the "issue" but insists I workaround it by making sure my items only relate to one category.   To do this, I need to first update all to blank (no category) then update all to the proper single category.    Otherwise, the new category gets added and I have 2 categories per item, and therefore the bug with inconsistent discounts.   

IMO the workaround is unacceptable and I / we should all have been notified of this change so we can test and work around it.   

I can only imagine what other changes have been made that I haven't detected.  Something like tax calculations could be difficult to detect and cost me $$$$.  

Is there an alert mechanism to know what changes were or will be made so that I can test and provide feedback?

[Lovewell]

@fireworksking I’m sorry you’re having some issues with an update. We use the square register and while I did notice there is not the option to be able to put an item into multiple categories, none of our items were automatically moved to multiple categories. If that is the case for you it sounds more like a bug with your account during the update. As I can’t see why square would have an update automatically remove items into multiple categories. 
unless I am misunderstanding which is entirely possible.