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I have several external hard drives, most encrypted with FileVault. Some with a 3rd party software called 'Espionage' (FileVault is better).

My MacBook Pro's internal hard drive suddenly started clicking and I can never start it up now. Hardware problem. Always starts clicking when I tried to start my MacBook.

I replaced it with an SSD. However, the old keychain encryption is lost. I still have the passwords but they are useless without the keychain encryption password generated by the computer that is stored in the damaged internal HD.

So am I in ruins with all my data from my internal HD gone and all my external hard drives?

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  • Please replace your headline by a better question (e.g. How do I recover Espionage encrypted folders if the main (encrypted) keychain is lost,,,?). I don't own Espionage, so I don't really know which and how the keychain is encrypted and can't edit it myself.
    – klanomath
    Commented Dec 28, 2016 at 14:47

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Chances are fairly good that your data is still intact on your old internal drive. It depends on exactly what part failed.

Send your old drive to a data recovery company. Drivesavers is one, there are others. They will do things like replace the controller card, or remove the platters and put them in a working drive.

Expect a bill somewhere between US$1000 and $2000.

For comparison purposes, an external backup drive costs about $150, and restoring a Time Machine backup takes an hour.

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  • I like the last sentence most ;-)
    – klanomath
    Commented Dec 28, 2016 at 22:43
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Unfortunately, yes your data is lost if you are not able to retrieve the encryption password. You may have some luck if you can find a way to mount your Mac internal HD with the encryption stored on it; you might want to look into your data recovery options for that drive if you want access to your other drives.

Another possibility is if your Keychain passwords were stored to iCloud somehow, but it sounds like that was not set up.

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If it just started clicking, you could be lucky and still copy all data before the disk dies.

  1. You may try to put your old harddisk in a Docking Station or external Thunderbold/Firewire/USB case.

  2. Manually copy your Keychain from ~/Library/Keychains to your new SSD. Reboot your MacBook. Now you should be able to access your previous keychain including 3rd party software keychains.

  3. If possible, create a complete backup using TimeMachine, CCC, Superduper…

Good luck.

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As @peter said, there is a high percentage of chances that your data is still intact. What I recommend, is that you try to backup everything with a software called Disk Drill (the full version cost 79€) I had the same problem and it worked.

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After installing the trial of Espionage and investigating the behavior of the app by checking fs_events my conclusion is:

Espionage doesn't write at all to ~/Library/Keychains and the passwords are stored in a plist-like database somewhere else.

Everything (including the different independently computed sparsebundle passwords) is saved to the file ~/Library/Application Support/com.taoeffect.Espionage3/database3. Older database3 files can be found in the folder ~/Library/Application Support/com.taoeffect.Espionage3/backups.

If you don't have a backup of your old system drive, the only possibility you have is to recover one of these files with a data recovery tool from the broken drive. You have to put the broken drive in an external case. Then use appropriate tools to recover one of the database3 files.

If you don't know how to do it and which tools to use, mandate a data recovery service. If they bill dependent on recovered data amount it should be cheap, because you only need the database3 file with a size of ~200 kb.

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