If someone regularly fasts the six days of Shawwal, are they obligated to fast them every year?
A person is not obligated to fast the six days of Shawwal every year, even if they have made it a habit. However, someone who regularly performs a good deed should not abandon it as long as they are able.
What is the ruling on fasting the six days of Shawwal?
Fasting the six days of Shawwal is Sunnah. The Prophet ﷺ said: "Whoever fasts Ramadan and then follows it with six days of Shawwal, it is as if they have fasted for a lifetime." [Narrated by Muslim]
This is because fasting one month of Ramadan is rewarded as fasting for ten months, and the six days are equivalent to sixty days, completing a full year of fasting.
What do you say about someone who stays up all night on Laylat al-Qadr but misses Fajr prayer?
Such a person has deprived themselves of a great reward. Performing obligatory acts is more beloved to Allah than voluntary acts. Fajr prayer is an obligation, and performing it in congregation is equivalent to worshiping for the entire night. So how can someone neglect it while striving for voluntary prayers?!
What is the wisdom behind the legislation of fasting?
Fasting is a divine school from which the believer learns much and trains in virtues that may be needed in life. Among these virtues is patience, as it is the month of patience. Fasting also teaches honesty and consciousness of Allah in both private and public, for there is no observer over the fasting person in abstaining from lawful pleasures except Allah alone.
Fasting strengthens willpower, sharpens determination, and nurtures mercy and compassion among the servants of Allah. It is a struggle against the self, a restraint of desires, a purification of the soul, and a cultivation of goodness.
The Prophetﷺ said: "Allah, the Almighty, said: ‘Every deed of the son of Adam is for him, except for fasting; it is for Me, and I shall reward for it. Fasting is a shield. So when one of you is fasting on a day, let him not engage in obscene speech or raise his voice in anger. If someone insults him or fights him, let him say: I am a fasting person. By Him in whose hand is the soul of Muhammad, the breath of the fasting person is more pleasant to Allah than the fragrance of musk.’" [Bukhari and Muslim]