PuTTY is a terminal emulator application which can act as a client for the SSH, Telnet, rlogin, and raw TCP computing protocols. PuTTY is commonly used for logging in to the servers. Before Stone Soup 0.5, numpad doesn't seem to work on connections from Windows users using both teraterm and PuTTY. As a workaround in PuTTY, you can go to Settings->Terminal->Keyboard and set your numpad type to NetHack (theres a little radio button for this). This changes so that instead of outputting arrow movements from the numpad it outputs vi-keys. Or you could insert keycodes into your macros file. Note well: Since NetHack mode effectively changes what the keypad types, the numrow will produce a different password than the keypad (for logging in to play once connected to CAO, CDO, or other servers, not to connect in the first place)
If even these settings are insufficient for your preferred numeric-key-padding ways, under Terminal -> Features, try checking the box for "Disable application keypad mode". This will cause +-/*enter on the keypad to behave as expected, and possibly other things. Der slinkmeister knows no fix for making shift-keypad5 do a long rest as per local mode. Control+Numpad does not work in 0.58 release, upgrading to 0.60 fixes this, and keeps all your old configurations.
If you are tired of right-clicks entering everything in your clipboard as input, you can disable this feature in Window->Selection->Control uses of mouse. Set action of mouse buttons to Windows. You can also Ctrl-right-click to bring up the normal context menu if you don't want to disable this feature.