When does the traveler begin to be permitted to shorten the prayer?
Chapter on the Traveler's Prayer
Al-Mughni
Book of Prayer
Primary text
Permission to shorten the prayer commences when the traveler exits the houses of his village and leaves them behind him. This view is held by Malik, Al-Shafi'i, Al-Awza'i, Ishaq, Abu Thawr, and several Tabi'in. The evidence for this is the verse: "And when you go forth [to travel] in the land, there is no blame upon you if you shorten the prayer" (Quran 4:101), meaning one must have physically departed. The Prophet, peace be upon him, began shortening the prayer immediately upon exiting Medina, as Anas reported praying four rak'ahs with him in Medina and two in Dhu al-Hulayfah. Therefore, shortening is permissible even when close to the houses if one has physically left them.
Supporting text
A view held by 'Ata' and Sulayman ibn Musa allows shortening the prayer within the town if the traveler intends to travel. Furthermore, some reports suggest that one should not shorten the prayer during the day of departure until nightfall, and similarly upon returning at night, one should not shorten until morning, though the primary evidence supports shortening upon physical departure.