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﴿ فَاسْأَلُوا أَهْلَ الذِّكْرِ إِن كُنتُمْ لَا تَعْلَمُونَ ﴾

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A man prays Witr before he sleeps and wakes up in the last part of the night to pray two rak'ahs; what is the ruling?

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Question:
I pray Witr before sleeping, but when I am free at night in the last third of the night, I pray two rak'ahs in the late night. What is the ruling on that? I may pray Witr and intend in my heart to pray two rak'ahs in the late night, because I turn to Allah, Glorified and Exalted is He, in this supplication at this time. Guide us, may Allah reward you with good. Is there a report from the Messenger of Allah (peace and blessings be upon him) regarding a specific supplication to be made at this time?

Answer:
The Prophet (peace and blessings be upon him) directed that Witr be prayed in the last part of the night, as that is the best time, provided it is possible. If a person is accustomed to waking up in the last part of the night, it is recommended that he pray his Witr in the last part of the night. However, if a person does not trust that he will wake up in the last part of the night except for the Fajr prayer, he should pray Witr before he sleeps, because the Prophet (peace and blessings be upon him) ordered some of his Companions to pray Witr before sleeping. He ordered Abu Hurayrah to pray Witr before sleeping because he was occupied with writing and narrating hadith at night, making it difficult for him to wake up in the last part of the night. If a person prays Witr in the early part of the night and then wakes up in the last part of the night, he should pray whatever is easy for him, and the first Witr is sufficient for him. He should not repeat Witr, because the Prophet (peace and blessings be upon him) forbade two Witr prayers in one night. He should be content with the first Witr and pray two rak'ahs or more in the last part of the night, as it is reported that the Prophet (peace and blessings be upon him) used to pray after the Witr as well. As for supplication in the last part of the night, there is no specific supplication prescribed. A person should strive to make comprehensive supplications that are beneficial for him, his parents, his brothers, and the Muslims in general. He should seek out supplications that contain good for him, his parents, and his Muslim brothers.
Source قناة «العلامة الدكتور صالح الفوزان»، رجل يصلي الوتر قبل أن ينام ويستيقظ في آخر الليل يصلي ركعتين فما الحكم؟ الشيخ صالح بن فوزان الفوزان — youtube.com

The Arabic text is a machine transcription of the audio recording.

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