Do Not Fast!
Although it is highly recommended to fast a great deal in the Month of Sha'ban but there are times in this month when scholars discourage fasting.
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Fasting at the end of Sha'ban
It was reported in al-Sahihayn from ‘Imran ibn Husayn, may Allah be pleased with him, that the Prophet (blessings and peace of Allah be upon him) said to a man:
“Have you fasted anything of the Sirar of this month?” He said: “No.” He said: “If you have not fasted, then fast two days.”
According to a report Reported by Al-Bukhari: I think he meant Ramadhan.
According to a report Reported by Muslim, (the Prophet, blessings and peace of Allah be upon him) said:
“Have you fasted anything of the Sirar of Sha'ban?”
(Reported by Al-Bukhari, 4/2000; Muslim, no. 1161).
There was some dispute as to the meaning of the word Sirar. The most well known view is that it refers to the end of the month. The end of the month is called Sirar because the moon is hidden (Istisrar) at that time. Someone may raise the point that it was reported in as-Sahihayn from Abu Hurayrah, may Allah be pleased with him, that the Prophet (blessings and peace of Allah be upon him) said: “Do not pre-empt Ramadhan by one or two days, except for those who have the habit of fasting regularly, in which case they may fast.” (Reported by Al-Bukhari, no 1983; Muslim, no. 1082).
How can we reconcile the Hadith which encourages fasting at this time with the Hadith which says not to fast at this time?
The answer is: many of the scholars and most of those who commented on this Hadith said: this man to whom the Prophet (blessings and peace of Allah be upon him) addressed this question was known to have the habit of fasting regularly, or else he had made a vow, so the Prophet (blessings and peace of Allah be upon him) commanded him to make up his fast. There are also other points of view on this issue.
3 Scenarios for fasting at the end of Sha'ban
In brief we may say that there are three scenarios for fasting at the end of Sha'ban:
The first scenario is when a person fasts at the end of Sha'ban with the intention of being on the safe side and not missing the first day of Ramadhan. This is forbidden.
The second scenario is when a person fasts with the intention of fulfilling a vow or of making up a day of Ramadhan that he missed or as an act of expiation (Kaffarah), etc. This is permissible according to the majority.
The third scenario is when this is purely a voluntary fast. This is regarded as Makruh by those who said that we should differentiate between Sha'ban and Ramadhan by not fasting for a while. Among those who said this was al-Hasan, may Allah have mercy on him. If it happens to coincide with a day when a person habitually fasts, Malik and those who agreed with him permitted this, but Ash-Shafi’i, al-‘Awza’i, Ahmad and others made a distinction between cases where it is a fast which a person habitually observes or otherwise.
In conclusion, the Hadith of Abu Hurayrah, may Allah be pleased with him, quoted above is what we should follow according to the majority of scholars. It is Makruh to observe a voluntary fast one or two days before Ramadhan for those who do not habitually fast on those days and who have not previously fasted until the end of Sha'ban.
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