The Kenwood TK290 software is DOS based. It will not run from Windows for programming ,because the Com port is not a true serial connection. The Windows version of a DOS prompt "polls" the port unlike DOS which has a solid connection to the com port.
There are several versions of the TK290 software. The latest I use is version 1.4.
It has a few more bells and whistles like a text at turn on that will say whatever you put in that window.