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I have a failing hard drive on my current MacBook Pro (it is having a symptom that I previously had on a failing hard drive on a MacBook – clicking drive noises).

I'm backing up my hard drive quite regularly using Time Machine and syncing some crucial files to Dropbox, but I'm afraid about the integrity of the data, meaning that if the hard drive fails, and I restore my Mac installation using Time Machine onto a new hard drive installed to the MacBook Pro, I'm afraid that some/all recent backed up data will be corrupt.

Will this happen?

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You can and should test the integrity of the data on the backup disk. There are various tools for doing this which no doubt others will comment on (I don't know the best one) but once done and passed, replace the drive and restore with confidence. –  Richard Mar 10 '12 at 18:43
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@Richard Why don't you suggest at least one tool for the job? Personally, I would find this information quite useful. –  cksum Mar 10 '12 at 22:01
    
Techtool Pro is what many use. I used it years ago but don't own it anymore: micromat.com/techtoolpro. I'm not in a position to recommend it, that's why I felt others would be better suited to posting this stuff. –  Richard Mar 10 '12 at 22:54
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@Richard As far as I was aware, it is impossible to check for data corruption unless a user has made a MD5 checksum before hand. Because files can contain any arrangement of bytes and data, only by having a point of reference (the checksum) can one compare files. But this requires a proactive approach. But unless you know something I don't, I'm not aware of any retroactive approach to verifying data corruption. I suppose for system files, it can be done (as presumably they will all carry the same checksum), but not for personal files (say a word document). –  cksum Mar 11 '12 at 23:32
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