How to add SSH key to PuTTY Agent at startup in Windows Server?

You can provide a path to the key on the Target command line in the shortcut

Create a shortcut to put in startup.
Right click -> properties
Modify the Target: section to add the key

C:\Program Files\putty\pageant.exe C:\Program Files\putty\keys\iain.ppk

When your system starts pageant will load the key and if it requires a pass phrase to unlock it it will ask for it.

You can add multiple keys on the pageant command line too e.g.

C:\Program Files\putty\pageant.exe C:\keys\iain.ppk c:\keys\user1.ppk

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