Systems and methods are provided for facilitating guided entry of a passcode. The exemplary guided passcode entry system provides additional security to traditional secret PIN or passcode entry systems by generating a randomized input sequence (order of entry) and prompting the user to input the passcode according to the randomized input sequence. The system also causes a test of the user's input data against a database of passcodes associated with the particular user for an exact match. The testing step can include comparing the characters of the input data to a particular passcode associated with the user which is stored in a database in accordance with the randomized input sequence in regard to the order that the input data was received. Based on the comparison of the received pin to the stored pin, the system can advance the transaction with the user.