Encountered bit of an issue with FreeProxy – it started to crash every few weeks. I suspect faulty hardware, some other service crashed as well.
Anyway I found it strange that it runs in service mode and doesn’t restart after crash. Later I remembered that services must be deliberately set to auto-restart mode if that wasn’t part of initial settings.
Services console
Windows console to manage services can be accessed by Control Panel > Administrative Tools > Services (may be unavailable, depends on user account) or by executing services.msc from command line.

services_console
Service recovery
Service properties have Recovery tab that defines behavior for when service is closed or crashed in inappropriate way.

services_properties_recovery
It allows to set different action for first, second and subsequent failures. Actions themselves are:
- restart service;
- restart computer;
- launch program of choice (with option to add fail count as parameter).
Overall
I know that there are some third party apps that monitor and restart services. As for me native Windows settings are quite robust and well integrated with event log as well.