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 an elderly person, a pregnant woman, or someone with a chronic illness to pay fidyah before Ramadan begins?
It is not permissible for an elderly person, a pregnant woman, or someone with a chronic illness to pay fidyah before Ramadan begins.
Additionally, it is not allowed to pay fidyah for more than one day in advance, because fidyah is a substitute for fasting, and fasting is not yet obligatory at that time.
However, it is permissible to pay fidyah for a single day in advance, by analogy with paying zakat up to one year in advance.
What is the ruling on someone who dies while having missed fasts?
● If a person dies before having the opportunity to make up the missed fasts—such as someone whose excuse (e.g., illness) persisted until their death—then no makeup fast (qada), fidyah, or sin applies to them.
● However, if they had the ability to make up the fasts but did not do so before passing away, the missed fasts must be compensated by giving a mudd of food for each missed day from their estate.
The Prophet ﷺ said: "Whoever dies while having a month’s fast due, one needy person should be fed per day on their behalf." [Narrated by At-Tirmidhi]
Additionally, a guardian (wali) may fast on their behalf, as the Prophet ﷺ said: "Whoever dies while having missed fasts, their guardian should fast on their behalf." [Narrated by Al-Bukhari and Muslim]
In another narration: "If they wish." This indicates that both feeding the needy and fasting on behalf of the deceased are permissible options.
What is the ruling on someone who eats or drinks while uncertain about the arrival of dawn, then later finds out that dawn had not yet broken?
If a person does this, their fast remains valid, as it is confirmed that they ate during the night. Similarly, if someone eats while uncertain and remains unsure whether they ate before or after dawn, their fast is still valid. This is based on the maxim of Sharia Law, which states: "Certainty is not removed by doubt." Certainty, here, is the presence of night, and the doubt concerns the arrival of dawn. Therefore, one relies on certainty and disregards doubt.