My experience with Windows is that it typically uses WMI (Windows Management Instrumentation) to read the SMART (self-monitoring and reporting technology) attributes of hard drives and solid state disks (SSDs). So unless one of those SMART attributes signals a failure condition, Windows can be somewhat oblivious to a problem. And by the SMART specification, once an attribute signals failure, the disk can fail completely in 24 hours. So by the time Windows reports a failure condition, it may be too late to do anything.

Good backups are essential! I don't think this can be stressed enough. Back up, back up, back up.

While there is no good excuse for not backing up, there are some good tools out there that do a better job than Windows when it comes to monitoring your disks. My favorite tool is called WindowSMART 2012. WindowSMART works with every desktop and laptop I have (10 total computers), running Windows XP right up through Windows 8, and it supports all of my external USB disks too. Hard drives and solid state disks alike are continuously monitored and reported, and it's got a nice UI for viewing and exporting results. The best feature is its remote notification capability--WindowSMART will send you an alert by email if a problem shows up, but it gets better than that. If you have an iPhone or Android phone, WindowSMART will send you an alert to that! WindowSMART's developer, Dojo North Software, is responsive to emails and bug reports. A friend of mine has a Windows Phone and emailed them asking about Windows Phone, and he got a response back the next day that Windows Phone integration was planned in the next release. There is a fee for WindowSMART but you can run it for a full 30 days before you have to decide, and upgrades after that are free. Check out WindowSMART 2012 if you want to have a peek at how your drives are doing.

If you have a hardware RAID array, and some of you high-end gamers might, then WindowSMART won't help you. It doesn't do hardware RAID, which is a bummer. There's another tool, HD Sentinel, which works with some RAIDs, but I think that one's a bit more expensive.