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After weeks of trying both objectives mentioned above, I could never retrieve a key I uploaded to keychain (always got a Nil value). The best I could accomplish was to load an outside generated key to keychain. Similarly, the key I generated from iOS keychain could never be added to our remote Windows server due to repeated server locks and error messages reported by Windows server admin. Not sure if these keys should be "treated" in any way before handing it to Windows admin. One can only spend so much time trying these things (50 + hours already) in XCODE, which is typically done in minutes in command prompt by the rest of the world in other operating systems. They are many youtube videos and Google article for these things. The biggest challenge was to try and fail with multiple combinations of dictionary query parameters hoping to get my key back for use.Finally I was able to leverage NMSSH (GIT) and use its method (in-memory public key, private key, PW option) to get authenticated to my user name in SSH server. The important point here is that we should be setting public key parameter as nil and allow the code to generate public key using private key and PW parameters. I would still like to hear from anyone that succeeded in in retrieving an externally generated key stored in keychain. I will be glad to provide any log file or other means to diagnose the issue.