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When I boot up or restart my computer, I sometimes get the countdown timer for running chkdsk and I usually bypass this and boot on into Windows. Is there a good frequency at which to allow your machine to run chkdsk or only when it's seriously needed to check the drive(s) for errors? Let me know if the specs of my machine are needed or if that is something that's not applicable to this question, thanks!

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Even sometimes is way to often. You should really elaborate why you get these chkdsk prompts. Since that there isn't an optmimal frequency for chkdsk. – nixda Dec 31 '12 at 1:52
Check this thread for causes of chkdsk: – Simon Verbeke Dec 31 '12 at 2:53
If CHKDSK is coming up every time then something might be wrong with your hard drive. Let it run and then restart your computer. Does it still appear? If so, check SMART and see if there are issues with your HDD. Are you running Windows XP? In addition to that, do you shut down your computer properly or hold the power button in? Windows sometimes runs CHKDSK if you shut off the computer incorrectly. – Sam Dec 31 '12 at 4:39
I must ask, why did this question get downvoted? – Sam Dec 31 '12 at 4:40
@nixda Thanks for the advice, true it is a case by case basis. – Christopher Chipps Dec 31 '12 at 4:45
up vote 1 down vote accepted

I'd ALWAYS do a chkdsk when a Windows system advises it be done....wait out the countdown and DO IT.

What this is telling you is that some file system structural error is likely on one of your disks (most likely C: if it is at reboot time) and that you CAN continue but you might further ruin your disk to the point where recovery efforts might not be possible.

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