That's strange. For the debugger, can you right click on the breakpoint column and try adding a conditional breakpoint there?
For the test explorer, what test framework are you using? You may want to try to go into the config and run the test manually. Also, since VS Code is an electron based application, you can pull up the debugger tools (similar to what is available in Chrome) and see any console outputs. There could be an issue and you'll get, hopefully, a more descriptive output.