A bulk IN endpoint should be set to return NAK at all times except when there is new data ready to go out in the endpoint's buffer. On receiving NAK, the host will try again, multiple times if needed.
So yes, if the host sends a SCSI command to request data, the device should accept the command and prepare the IN endpoint to send the data. Typically, the device triggers an interrupt AFTER the IN endpoint sends data so it can prepare to refill the buffer if needed.