'Imran bin Husain (RA) reported that the Apostle of Allah (ﷺ) said to him (or he said to another person and he was listening to it): O, so and so, did you observe fast in the middle of the month? He said: No. Thereupon he (the Messenger of Allah) (ﷺ) said: When you break it, then observe fast for two days.
'Imran bin Husain (RA) reported Allah's Messenger (may peace he upon him) having said to him or to someone else: Did you fast in the middle of Sha'ban? He said: No. Thereupon he (the Holy Prophet) said: If you did not observe fast, then you should observe fast for two days.
Imran bin Husain (RA) reported that Allah's Apostle (ﷺ) (may peace heupon him) said to a person: Did you observe any fast in the middle of this month (Sha'ban)? He said: No. Thereupon the Messenger of Allah (ﷺ) said: Fast for two days instead of (one fast) when you have completed (fasts of) Ramadan.
Explanation & Benefits
Shaykh Maulana Abdul Aziz Alvi
Hadith Commentary: Benefits and Issues: According to the majority of linguists and scholars of hadith, (sararu) refers to the last days of the month, because during these days the moon becomes hidden. According to some, it refers to the initial days of the month, and according to others, it is derived from (surrat al-shahr) (its middle and center), and the "white days" (ayyam al-beed) are meant.
Source: Tuhfat al-Muslim: Commentary on Sahih Muslim, Page: 2745
Shaykh Abdul Sattar al-Hammad
Hadith Commentary:
Imam Bukhari rahimahullah has mentioned in the chapter heading, in an absolute sense, the fasting at the end of the month, whereas in the hadith, the mention is specifically of the end of the month of Sha'ban. From this, it is understood that according to Imam Bukhari rahimahullah, fasting at the end of any month in general is legislated, so that a person becomes accustomed to it.
Whereas, in another hadith, it is stated that fasting one or two days before Ramadan is prohibited.
This applies in the case when the fasts are observed with the intention of welcoming (istiqbal) Ramadan. If there is no such intention, but rather it is a person's habit, then there is no objection to fasting at the end of Sha'ban.
Source: Hidayat al-Qari: Commentary on Sahih Bukhari, Urdu, Page: 1983
Shaykh Umar Farooq Saeedi
Benefits and Issues:
➊ This hadith apparently contradicts the previous hadith in which it is stated that one should not fast a day or two before the start of Ramadan. However, the reconciliation between them is that this concession and emphasis is for the person who has made a vow (nadhar) to fast, or who is accustomed to fasting on specific days from before; such a person should continue to fast as usual. But if someone, without any prior habit or vow, wishes to fast voluntarily as a way of welcoming Ramadan, then it is not permitted.
➋ The person whom the Prophet sallallahu alayhi wa sallam instructed to fast one or two days after Ramadan was someone who used to fast at the end of the month, but he had left off fasting at the end of Sha'ban out of fear that it might fall under the category of welcoming Ramadan, which is prohibited.
➌ The various meanings of the word (sarara) are mentioned after the following narration.
Source: Sunan Abu Dawood – Commentary by Shaykh Umar Farooq Saeedi, Page: 2328