Until recently, putty was both manually and automatically grouping for me. However, automatic grouping seems to have broken around putty version 0.75. The release notes (https://www.chiark.greenend.org.uk/~sgtatham/putty/) mention the use of named pipes instead of window messages for communicating with pageant. I wonder if there was a broader change and groupy is no longer able to intercept / "grab" the putty window when it opens. I'm hoping the groupy programmers fix this, as grouping putty windows was my primary reason for purchasing the software.
Other programs (e.g., cmd.exe) still group correctly. And I can use the older version of putty on the same system and that still groups correctly. I've reproduced those differences in behavior between versions 0.74 and .076 of putty on the two systems where I run groupy. In fact, I named one putty74 and the other putty76. The first automatically groups, the second does not.
My two systems are both Win10 -- one is 20H2, the other 21H1. I have Groupy v1.49.1 installed on both.
