Is you client set receive that particular file? Check the file extension. Then check the following:
File>Options>DCC>Folders...
Click on the blank drop down menu...Is that file type listed? If not just add the file type by typing:
Example: *.exe
Then click the "ADD" button.
If it is already added, make note that this is just a suggestion. Not guaranteeing that it is the problem. Hope its useful.