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.
Is it permissible to pay the expiation of an oath to a charitable party as it feeds the poor and needy such as Tkiyet Um Ali?
There is no harm on authorizing someone to handle the expiation of another to the poor and needy, since Shafiee's jurists stated that authorizing someone for the purpose of distributing Zakah, expiation and vow is permissible as stated in [Mughni Al-Muhtajj,vol.3/pp.237]. At last, the intention of the person who intends to authorize someone else suffices in this regard. And Allah Knows Best.
What type of illness that permits breaking the fast in Ramadan?
It is an illness that, if one fasts, there is a fear it may lead to their death or cause unbearable hardship.
What is the ruling on a woman who takes medication to delay menstruation for fasting?
If a woman takes medication (to delay menstrual period) and does not experience menstruation, her fast is valid. However, she is not advised to do so unless there is a necessity.
If the medication harms her, even potentially, it is forbidden (haram) for her to take it.