So you can always upload, but using serial monitor after that often fails?
If you use a 32U4 based board (e.g. Leonardo), you can program your cleanup to act as a HID and send some keystrokes M)to open the serial monitor.
For most other boards, the answer is no, you can't control the PC from the Arduino without additional software running on the PC.
But you should fix the root cause of the issue instead of using workarounds.