Hadith 527

عن أبي هريرة رضي الله عنه قال : قال رسول الله صلى الله عليه وآله وسلم :« لا تقدموا رمضان بصوم يوم ولا يومين ،‏‏‏‏ إلا رجل كان يصوم صوما فليصمه». متفق عليه.
Abu Hurairah (RAA) narrated that The Messenger of Allah (ﷺ) said: "None of you should fast a day or two before the (beginning of the) mouth of Ramadan, unless it is a day on which one is in the habit of fasting (i.e. voluntary fasting that coincides with that day).” Agreed upon.
Hadith Reference بلوغ المرام / 527
Hadith Grading محدثین: صحيح
Hadith Takhrij «أخرجه البخاري، الصوم، باب لا يتقدم رمضان بصوم يوم ولا يومين، حديث:1914، ومسلم، الصيام، باب لا تقدموا رمضان بصوم يوم ولا يومين، حديث:1082.»
Related hadith on this topic
Explanation & Benefits
Shaykh Safi ur-Rahman Mubarakpuri
Lexical Explanation 527:
Kitab al-Siyam: The literal meaning of "al-siyam" is "al-imsak," that is, to abstain. In the legal (shar‘i) sense, it means to abstain, according to the prescribed method, from eating, drinking, and sexual intercourse from the break of dawn (fajr) until sunset (maghrib). Additionally, refraining from vain talk, idle speech, and disliked or forbidden words is also included in this. Fasting (sawm) was made obligatory in the 2nd year of Hijrah.

La taqaddamu: This was originally "la tataqaddamu," meaning: Do not fast one or two days before Ramadan in anticipation of Ramadan.

Kana yasumu sawman: That is, as per his usual practice, he would fast on certain specific days, and those days happened to fall in the last days of Sha‘ban. For example, a person habitually fasts every Monday, and this Monday falls at the end of Sha‘ban; then there is no objection for this person to fast on that day—he may fast as per his usual practice.

Falyasumhu: In this, the "lam" is for command, indicating permissibility; that is, such a person may fast one or two days before Ramadan as per his usual practice.

Benefit 527:
From the mentioned hadith, it is understood that it is not permissible to fast before the commencement of Ramadan, except for a person whose regular practice, according to the Sunnah, is to fast on Mondays and Thursdays, and if Monday or Thursday falls on the 29th or 30th of Sha‘ban, or someone who is making up missed fasts (qada) and these are completed on the 29th or 30th of Sha‘ban. In these cases, or in any other similar coincidental situation, there is no harm in fasting. And Allah knows best.
Source: Bulugh al-Maram: Commentary by Safiur Rahman Mubarakpuri, Page: 527
Maulana Dawood Raz
Hadith Commentary:

For example, if someone habitually fasts on Mondays or Thursdays each month, or on any other specific day each week, and by coincidence that day falls in the last dates of Sha’ban, then he may observe that fast. The prohibition of fasting after the middle of Sha’ban has also been mentioned so that one’s strength remains preserved for Ramadan and weakness does not befall him.

In short, at every step, keeping the commands and prohibitions of the Shari’ah in view is itself the religion, this is worship, this is Islam, and this is faith (iman). One must never, ever allow one’s own intellect to interfere at any point.
Source: Sahih Bukhari: Commentary by Maulana Dawood Raz, Page: 1914
Shaykh Abdul Sattar al-Hammad
Hadith Commentary:
(1)
In anticipation of Ramadan, it is not permissible to fast one or two days before this blessed month. However, due to specific circumstances, fasting on these days is allowed, the details of which are as follows:
٭ If a person habitually fasts on Mondays or Thursdays, and coincidentally the last day of Sha'ban falls on a Monday or Thursday, then it is permissible to fast on that day.
٭ If someone has missed obligatory fasts (qada) to make up, he may observe them one or two days before Ramadan.
٭ Expiatory (kaffarah) and vowed (nadhar) fasts may also be observed on these days. However, it is not correct to fast one or two days before Ramadan with the intention of welcoming Ramadan, because the Messenger of Allah (sallallahu alayhi wa sallam) has made the fasts of Ramadan conditional upon the sighting of the crescent moon (ru’yat hilal).
Thus, the sighting of the crescent moon is the cause (‘illah) for the fasts of Ramadan, and whoever fasts one or two days before Ramadan as a form of anticipation has cast aspersion upon this cause and has deemed it defective.

(2)
Hafiz Ibn Hajar (rahimahullah) writes that, as a precaution, it is prohibited to fast a welcoming fast one or two days before Ramadan. Imam Tirmidhi (rahimahullah) has also stated the same meaning for this hadith. (Fath al-Bari: 4/165)
The reason for this prohibition is so that one may have strength and vigor for the upcoming fasts of Ramadan, and also so that a voluntary (nafl) fast, when joined with the obligatory (fard) fasts, does not create doubt among the people.
Source: Hidayat al-Qari: Commentary on Sahih Bukhari, Urdu, Page: 1914
Hafiz Muhammad Ameen
The disagreement among the students of Abu Salamah is that Yahya ibn Abi Kathir has attributed this hadith to the narration of Abu Hurairah radi Allahu anhu, whereas Muhammad ibn Amr has attributed it to Abdullah ibn Abbas radi Allahu anhu. Muhammad ibn Amr has made a mistake. The evidence for this is that Muhammad ibn Amr has also narrated in accordance with the narration of Yahya ibn Abi Kathir. See (Dhakheerat al-‘Uqba: 21/5)
Source: Sunan Nasa'i: Translation and Benefits by Shaykh Hafiz Muhammad Amin Hafizullah, Page: 2175