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I'm on Ubuntu 12.04. When I try to connect to our server

ssh user@server -p 1234 -i ~/path/to/my/private-key

it asks me 3 times for the private key's passphrase and finally fails, though I always enter the correct one. When I try it with Putty (converted the OpenSSH key to .ppk) it works without any problem. What could be the reason?

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What are the permissions of the key? I doubt that's the issuesince usually you'll get an error from other server, but worth checking. – nerdwaller Feb 16 '13 at 16:54
    
They are readable/writable by the user only. – Mike L. Feb 17 '13 at 7:21

Try adding -v (verbose) option to the ssh command line, it could give you a hint.

Also make sure you really have the correct passphrase: try changing it with ssh-keygen -p

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