Do the Angels Look Down from Heaven upon Those Who Pray Tahajjud?
Question

If I pray Witr with `Isha’, will I be one of those who pray Qiyam Al-Layl [voluntary prayers at night], and will my house be known to the angels? As Ibn Rajab  al-Hanbali said: Ka`b said: The angels look down from heaven upon those who pray tahajjud at night as you look at the stars of the sky. Ibn al-Haj said in al-Madkhal: There are many benefits in praying Qiyam Al-Layl, so the seeker of knowledge should not miss out on any of that. Those benefits include:… 5. The angels see his place from heaven as the shining stars appear to us in the sky.
Praise be to Allah.Virtues of Qiyam Al-Layl
Qiyam Al-Layl is one of the best acts of worship that raise a person in status, increases good deeds, absolves his bad deeds, and brings him closer to the Lord of all creation. Praying Qiyam Al-Layl is encouraged in the book of Allah, may He be exalted, and in the Sunnah of His Prophet (blessings and peace of Allah be upon him).
Do the Angels look down from heaven upon those who pray Tahajjud?
We do not know of anything in the texts of the Quran or Sunnah to indicate that the angels look down from heaven on those who pray tahajjud at night, and could see them in their places on earth as the stars of the sky appear to the people of earth.
What is narrated from Ka`b Al-Ahbar about him saying that “The angels look down from heaven upon those who pray tahajjud at night as you look at the stars of the sky” was mentioned by Al-Hafiz Ibn Rajab in his book Ikhtiyar Al-Awla fi Sharh Hadith Ikhtisam al-Mala’ Al-A`la (p. 91), where he said:
“Karaz ibn Wabirah said: I heard that Ka`b said: The angels look down from heaven upon those who pray tahajjud at night as you look at the stars of the sky.”
This is not soundly narrated from Ka`b, because the chain of narration is munqati` (interrupted); Karaz ibn Wabirah did not state who narrated that to him from Ka`b; rather he conveyed it from Ka`b (without mentioning the narrator in between).
Nothing is known about the status of Karaz ibn Wabirah as a narrator.
Even if we assume that the report is proven to be from Ka`b, it does not prove anything, because Ka`b was one of the Successors, one of the People of the Book who became Muslim, and he often quoted from the scriptures of the People of the Book, and that does not constitute proof.
Similarly, the words of Ibn Al-Haj in Al-Madkhal (2/137): ‘The angels see his place from heaven as the shining stars appear to us in the sky’ do not count as evidence. The most that can be said concerning this is that he was narrating the meaning from Ka`b.
Rather what counts as proof and evidence is the texts of the Quran and Sunnah .
Reciting Quran is light for a person, especially if he recites it in prayer. Imam Ahmad (11774) narrated from Abu Sa`id Al-Khudri that a man came to him and said: Advise me. He said: I asked the Messenger of Allah (blessings and peace of Allah be upon him) for the same thing before you that you have asked me for, and he said: “I advise you to fear Allah, for that is the foundation of everything. And you should strive in jihad, for it is the monasticism of Islam. You should remember Allah and recite the Quran, for it is your comfort in heaven, and will bring renown for you on earth.” (Classed as hasan by Al-Albani in Sahih Al-Jami` (2543)
Ibn Hibban narrated in his Sahih (361) from Abu Dharr that the Prophet (blessings and peace of Allah be upon him) said: “You should recite the Quran and remember Allah, for that will be light for you on earth and will be stored up for you in heaven.” (Classed as hasan by Al-Albani in Sahih At-Targhib (1422)
Al-Bayhaqi narrated in his Sunan (162) that `Ali (may Allah be pleased with him) said: We were instructed to use the siwak and he [the Prophet (blessings and peace of Allah be upon him)] said: “When a person stands to pray, the angel comes to him and stands behind him, listening to the Quran and drawing closer, and he continues to listen and draw closer until he puts his mouth to his mouth, so he does not recite any verse but it goes inside the angel.” (Classed as sahih by Al-Albani in As-Sahihah (1213)
So prayer at night is light, and it is attended by the angels of mercy. This is proven. As for what is mentioned of the words of Ka`b, there is no proof of that.
 Tahhajjud prayer time
The time for praying Qiyam Al-Layl begins after `Isha’ prayer and lasts until the break of dawn. The best of it is the last third of the night.
The scholars of the Permanent Committee said:
“The time for praying Qiyam Al-Layl and Witr is from after `Isha’ prayer until the break of dawn.” (Fatawa al-Lajnah Ad-Da’imah (7/225)
Ibn Baz (may Allah have mercy on him) said:
“The time for tahajjud begins after `Isha’ and ends with the break of dawn. When the people have prayed `Isha’, the time for tahajjud begins and lasts until the break of dawn. The Sunnah is to pray Qiyam Al-Layl between the end of `Isha’ prayer and the break of dawn, even if it is one rak`ah of Witr.” (Fatawa Nur `ala Ad-Darb (10/70)
Whatever prayer you offer after `Isha’ prayer comes under the heading of Qiyam Al-Layl. People vary in status in that regard, and their reward will vary according to how long they spend in Qiyam Al-Layl and other righteous deeds. Whoever prays two rak`ahs after `Isha’, they are regarded as coming under the heading of Qiyam Al-Layl, but the one who prays two rak`ahs and Witr after `Isha’ is not like one who gets up at night and prays as much as Allah wills that he should pray.
The reward and the virtue are commensurate with the level of the deed.
And Allah knows best.