A lot of people assume that sending prayers upon the Prophet is something to be looked down upon or left to the realms of those who commit religious innovations. Such a view is completely erroneous. The Prophet (peace be upon him) was no more than a man, but the best of mankind. He was no more than a Prophet, but the sayyid, leader and seal of all Prophets. He was no more than a messenger, but one who delivered the greatest and complete message.
The Prophet (peace be upon him) said: ‘Whoever sends a prayer upon me, Allah sends ten upon him.’
The Prophet (peace be upon him) said: ‘Do not take my grave as a place of habitual ceremony. Send prayers upon me, for verily your prayers reach me wherever you are.’
The Prophet (peace be upon him) said: ‘A miser is one whom when I am mentioned to him, fails to send prayers upon me.’
The Prophet (peace be upon him) said: ‘Among the most excellent of your days is Friday because on that day Adam was created, and on that day he died, and on that day the Trumpet will be sounded, and so on it shall come the Hour. So invoke blessings on me frequently on that day, for your blessings will be brought to me.’ He was asked, ‘Oh Messenger of Allah, how will our blessings be conveyed to you when your body has become part of the decaying earth?’ He replied, ‘Allah has prohibited the earth from destroying the bodies of the Prophets.’
The Prophet (peace be upon him) said: ‘When any Muslim sends greetings to me, Allah returns my soul to me so that I may respond to his greetings.’
Other instances when it is recommended to send Salah on the Prophet (peace be upon him) is on entering a masjid, leaving a masjid, and in the tashahhud of the daily prayers. Also when passing by the grave of the Prophet (peace be upon him).
Many of the ancient scholars opined that salah upon the Prophet means mercy. According to this opinion, when one prays to Allah, he is asking for Allah’s mercy, and if he prays upon the Prophet, he is asking Allah to have mercy on the Prophet (peace be upon him).Ibn al-Qayyim was of the view that for Allah to pray over His Prophet means Allah’s praise for the Prophet in the heavens. This is substantiated by a narration in al-Bukhari that Abu al-‘Aaliya said: ‘Allah’s prayer upon His Prophet is for Him to praise him amongst His angels.’
According to this view, for the angels or human beings to send prayers upon the Prophet, is asking Allah to praise the Prophet and exalt his status.
The word ‘Aal’ in the Arabic language refers to a person’s family as it also refers to his followers. Hence, the scholars have differed with respect to the word ‘Aal’ that occurs in the syntax of prayers upon the Prophet, as to what exactly it refers to.One view (favoured by the Shi’ite) is that ‘Aal’ refers to those of the Prophet’s family to whom it is forbidden to give Zakah. Another view (endorsed by the Hanbali school of law) is that ‘Aal’ refers to all those who follow the Prophet (peace be upon him) until the Day of Resurrection. This is also reportedly the view of the Companion, Jabir ibn ‘Abdullah. Some Hanbalis such as Ibn Qudama and al-Majd Ibn Taymiyya (the grandfather of shaikh’l-Islam Taqi’d-din ibn Taymiyyah) held that ‘Aal’ refers to God-fearing members of the ummah.
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 Narrated ’Abdur-Rahmaan bin Abee Laylah: Ka’b bin ’Ujrah met me and said, ‘Shall I not give you a present I got from the Prophet (sallallaahu ’alaiyhi wa sallam)?’ ’Abdur-Rahmaan said, ‘Yes, give it to me.’ He said, ‘We asked Allaah’s Messenger (sallallaahu ’alaiyhi wa sallam) saying, ‘Oh Allaah’s Messenger! How should one (ask Allaah to) send As-Salaah upon you and the Ahlul-Bayt (the members of the family), for Allaah has taught us how to greet you?’ He said, ‘Say, Allahumma salli ’alaa muhammadin wa ’alaa aali muhammadin, kamaa sallayta ’alaa ibraaheema wa ’alaa aali ibraaheema innaka hameedun majeed. Allahumma baarik ’alaa muhammadin wa ’alaa aali muhammadin, kamaa baarakta ’alaa ibraaheema wa ’alaa aali ibraaheema innaka hameedun majeed. Saheehul-Bukharee 4/589