Sheikh Saalih was asked about a person who commits a sin again & again repeatedly, will Allah forgive him if he makes tauba?
Sheikh answered that if a person makes tauba after doing sin, and the repentance is based on sincerity with the aim of leaving the sin then ALLAH will forgive him, inshAllah.
He quoted that how people become kafir during the era of Abu Bakr (May Allah Be Pleased With Him) and then they repented and Abu Bakr treated them as muslims. So who are we to discourage someone from repentance if is only a sinner and not a kafir.
He said it is not to encourage people to commit sin but rather it is to motivate people to make tauba. Hazrat Ali (May Allah Be Pleased With Him) was asked about a person who commits sin after tauba he said:
“He should ask Allah for forgiveness and repent.” It was said, “For how long?” He said, “Until the Shaytaan is defeated.”