Elif and if not working or me not understanding [duplicate]

by 
if passretry == 'yes' or 'Yes':

the above if statement is evaluated as: –

if (passretry == 'yes') or 'Yes':

Now, since 'Yes' is evaluated to True, so, your if statement is always True, and hence you always have to enter new password.

You need to change the condition to: –

if passretry in ('yes', 'Yes'):

likewise, the following elif should be changed to: –

elif passretry in ('no', 'No'):

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