Yes, the Prophet ﷺ did pray Taraweh in Jamat for three nights and then stopped.
أَخْبَرَنِي عُرْوَةُ، أَنَّ عَائِشَةَ رَضِيَ اللَّهُ عَنْهَا، أَخْبَرَتْهُ: أَنَّ رَسُولَ اللَّهِ صَلَّى اللهُ عَلَيْهِ وَسَلَّمَ خَرَجَ لَيْلَةً مِنْ جَوْفِ اللَّيْلِ، فَصَلَّى فِي المَسْجِدِ، وَصَلَّى رِجَالٌ بِصَلاَتِهِ، فَأَصْبَحَ النَّاسُ فَتَحَدَّثُوا، فَاجْتَمَعَ أَكْثَرُ مِنْهُمْ فَصَلَّى فَصَلَّوْا مَعَهُ، فَأَصْبَحَ النَّاسُ فَتَحَدَّثُوا، فَكَثُرَ أَهْلُ المَسْجِدِ مِنَ اللَّيْلَةِ الثَّالِثَةِ، فَخَرَجَ رَسُولُ اللَّهِ صَلَّى اللهُ عَلَيْهِ وَسَلَّمَ فَصَلَّى فَصَلَّوْا بِصَلاَتِهِ، فَلَمَّا كَانَتِ اللَّيْلَةُ الرَّابِعَةُ عَجَزَ المَسْجِدُ عَنْ أَهْلِهِ، حَتَّى خَرَجَ لِصَلاَةِ الصُّبْحِ، فَلَمَّا قَضَى الفَجْرَ أَقْبَلَ عَلَى النَّاسِ، فَتَشَهَّدَ، ثُمَّ قَالَ: أَمَّا بَعْدُ، فَإِنَّهُ لَمْ يَخْفَ عَلَيَّ مَكَانُكُمْ، وَلَكِنِّي خَشِيتُ أَنْ تُفْتَرَضَ عَلَيْكُمْ، فَتَعْجِزُوا عَنْهَا»، فَتُوُفِّيَ رَسُولُ اللَّهِ صَلَّى اللهُ عَلَيْهِ وَسَلَّمَ وَالأَمْرُ عَلَى ذَلِكَ
Urwa narrated that (Sayidah) Aishah (May Allah Most High be pleased with her) informed him that one night the Messenger of Allah ﷺ went out in the middle of the night and prayed in the Masjid and some men prayed behind him . In the morning, people spoke about it. So a larger number of them gathered and prayed behind him (on the second night). The next morning the people spoke about it. So on the third night the Masjid was full of people. The Messenger of Allah ﷺ came out and the people prayed behind him ﷺ. When the fourth night arrived the Mosque was overwhelmed with people and could not accommodate them. However, he ﷺ came out for the Fajr prayer (and not for night prayer). When the Fajr prayer was complete he ﷺ recited Shahadah and said, ‘Now indeed your presence (in the Masjid) was not unknown to me. However, I was afraid that it may become obligatory upon you, and you may not be able to fulfil it.’ The Messenger of Allah ﷺ passed away and the situation remained like that’. (Sahih al-Bukhari, 2012).
We see in the Hadith above that the Prophet ﷺ did pray Taraweh in Jamat for three nights and then stopped. On the forth night the blessed Prophet ﷺ did not lead the people in Salah despite them waiting for him . The blessed Prophet ﷺ refrained from leading the Sahaabah in Jama’ah for Taraaweeh prayer on the fourth night even though he had done so for the previous three nights. This was done by the Prophet ﷺ as a mercy to his Ummah. He did not want the Taraaweeh prayer to become an obligation upon us, as explained in the Hadith above.
قَالَ الْقَاضِي أَبُو بَكْرٍ يَحْتَمِلُ أَنْ يَكُونَ اللَّهُ تَعَالَى أَوْحَى إلَيْهِ أَنَّهُ إنْ وَاصَلَ هَذِهِ الصَّلَاةَ مَعَهُمْ فَرَضَهَا عَلَيْهِمْ. (المنتقى شرح الموطإ)
Qadi Abu Bakr said, it is possible that Allah (Most High) had revealed to him , that if he continues this prayer with them then He (Most High) will make it obligatory upon them. (Imam al-Baaji, al-Muntaqaa Sharh al-Muwatta).
Since the final action of the Prophet ﷺ was to refrain from praying the Taraaweeh prayer in congregation (Jama’ah), that became the established Sunnah. So why do we pray it in Jama’ah now? This is due to Sayidina Umar (May Allah Most High be pleased with him) establishing Jama’ah for it. See the link below for details.
And Allah Most High Knows Best.
-Answered by Shaykh Noorud-deen Rashid (25.04.2022)
Is it Bidah to pray Taraweeh in Jamat?
What is Bidah?
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