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.
When is supplication (du‘a) more likely to be accepted: before or after breaking the fast in Ramadan?
Du‘a is accepted at all times, and this is part of Allah’s mercy and generosity toward His servants.
The Prophet ﷺ said: "No Muslim makes a supplication that does not involve sin or severing family ties except that Allah grants them one of three things: either He grants their supplication immediately, or He stores it for them in the Hereafter, or He averts from them an equivalent harm." [Narrated by Ahmad]
However, in Ramadan, du‘a is especially likely to be accepted shortly before breaking the fast.
The Prophet ﷺ said: "Three supplications are never rejected: the supplication of a fasting person until they break their fast, the supplication of a just leader, and the supplication of an oppressed person. Allah raises it above the clouds, opens the gates of heaven for it, and says: ‘By My might, I will surely grant you victory, even if after a while.’" [Narrated by Al-Tirmidhi]
What is the ruling on performing Tahajjud after the Witr?
Praise be to Allah, and peace and blessings be upon our Master, the Messenger of Allah.
It is permissible for one who has prayed the Witr to perform voluntary (Nafl) prayers after it. However, it is preferable for the Witr to be the final prayer of the night. Therefore, if a person is confident that they will wake up during the night for Tahajjud, it is recommended for them to delay the Witr until after the Tahajjud. Conversely, if one fears they may not wake up, they should perform the Witr before sleeping.
Al-Khatib al-Shirbini (may Allah have mercy on him) stated: 'It is not disliked (Makruh) to perform Tahajjud after the Witr, but it is not recommended to do so intentionally.' [Mughni al-Muhtaj, Vol. 1/P.454]. And Allah the Exalted knows best."
What is the ruling on wiping the head during ablution from behind a barrier like a headscarf (hijab)?
The obligation in ablution is to wipe some of the head; it is not a condition to wipe all of it. As for one who has a turban or headscarf on their head, it is permissible for them to wipe over it after wiping a part of their head in any place. This is easily done at the front of the head. This means the woman begins by wiping the front of her head from under the headscarf, then completes the wiping to the back of the head from over the headscarf. If the woman wipes over the headscarf on her head and the moisture reaches the scalp or some hair within the boundaries of the head, it suffices for wiping the head. And Allah the Almighty knows best.