The first question I have to ask relates to your statement on how long it takes to retrieve the data.   Admittedly, there are a lot of pieces, but stop and...

Whether or not someone works multiple shifts isn't the biggest problem, but having data that represents multiple consecutive "clock punches" of the same type (either IN or OUT), seems illogical. ...

You might be able to use the command window (cmd.exe) to run the command:

          echo thisismypassphrase | C:\YourPath\gpg.exe --option1 --option2 ...