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Passphrase question


We have recently started using WinSCP and I have a specific destination that I have to enter a Passphrase for the key before it will connect. Once I enter the passphrase everything works and I can upload the files. I want to be able to use the " Keep directory up to date" option however it appears the connection doesn't connected. When the software tries to reconnect I get prompted for the passphrase again.
With all that being said is there a way to automate the Passphrase for the key? I have attached a few screen shots.

Version - 5-13-4 Build 8731
Microsoft version - server 2016 Version1607
Protocol - SFTP

Thank you for any advice.