Can someone who begins a voluntary fast break it?
It is preferable for someone who begins an act of worship not to break it.
Allah the Exalted has said {what means}: "and let not your [good] deeds come to nought!" [Muhammad/33].
However, if a person starts a voluntary fast (nafl) and needs to break it, they are going against what is preferable, but there is no sin upon them.
Is it permissible for a woman to wear underwear while performing Umrah?
Yes, it is permissible for a woman to wear underwear while performing Umrah. This is because she should keep her regular clothes that cover all her body while being in a state of Ihram (ritual consecration) for Hajj, or Umrah. However, she should uncover her face and hands, but it is permissible for her to let her head-covering garment drape from her head down over her face when non-Mahram (i.e., marriageable) men pass by her. And Allah Knows Best.
What is the ruling on deliberately breaking the fast while being capable of fasting?
Whoever intentionally breaks their fast in Ramadan without a valid excuse has committed a major sin and bears great guilt. They must repent, seek forgiveness, refrain from eating and drinking for the rest of the day, and make up for that day after Ramadan.
They have lost an immense reward, which cannot be compensated even by fasting an entire lifetime as a voluntary act, because an obligatory fast cannot be equaled by voluntary fasting.
If the fast was broken through sexual intercourse, the person must:
● Make up for the missed fast (qada), and
● Perform kaffarah by fasting two consecutive months.
● If they are unable to do so, they must feed sixty needy people.
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.