Sad to say, it DOES NOT REMEMBER ANYTHING! Build 220.127.116.11 installed. Open SSMS. First time customizing the buttons, I saw every RG Toolbar option AND the SQL Prompt menu options. Exit SSMS, having changed nothing.
Start SSMS. Re-position toolbar. Customize: at least it only showed the four installed add-in icons this time around. Re-sequenced icons and changed all of them to "Default" (Icon only). Close SSMS.
Restart and it's as if I never changed a thing! WHAT A DISAPPOINTMENT!
I can really feel your pain. I've had a look at the code, and even made an attempt to fix it. Unfortunately it will take more time and effort to sort out than I have available. There's growing awareness within Red Gate about how badly the toolbar works. Sorry, that's all the comfort I can offer at the moment.
This is exactly why I would never give Redgate a nickle. They can't even do toolbars right. In 2015. They are literally the only add-in maker on earth that can't get simple menu persistence down. DO they realize how utterly incompetent and stupid this makes them look?