I have trouble with VS 2015 and Typescript compile on save. If I enable combine all outputs into one file that output file will not be updated on save. During build the file
It's an old question, but I had a different resolution:
Make sure your TypeScript version is installed/available. I'd opened an old project and it was set as 3.6 (unavailable). Updating the version to 3.8 (which was installed) fixed it.