Probation Log-in Program?

[Gribouillis]

I'm just curious if this is achievable in Python

It is probably achievable in Python, because Python can for example open a web page in a web browser and also emulate mouse clicks and keyboard input at given positions on the screen, but if the site uses CAPTCHAS which purpose is precisely to discriminate robots from humans, it may be very difficult to achieve. Also if the site is modified someday or a captcha is added someday, the bot will be unable to login that day.