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﴿ فَاسْأَلُوا أَهْلَ الذِّكْرِ إِن كُنتُمْ لَا تَعْلَمُونَ ﴾

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The reason the Prophet (peace and blessings be upon him) supplicated for those who shaved their heads three times and for those who shortened their hair once

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The questioner : Yes. May Allah reward him. Ibn Kathir (may Allah have mercy on him) mentioned in the story of the Treaty of Hudaybiyyah that when the Prophet (peace and blessings be upon him) supplicated for the shavers for forgiveness three times and for the shorteners once, they said, “Why, O Messenger of Allah?” He said, “Because they did not complain.” So he made the reason for the supplication the lack of complaint, because those who shortened their hair seemed to have complained when they came out from Umm Salim.

The Shaykh : By Allah, I do not know about the authenticity of this hadith. I say I do not know about its authenticity, because those who shortened their hair had already exited the state of ihram, so they no longer had any complaint. However, the shavers were better because they shaved all the hair, and hair in that era was an adornment, an adornment that it was difficult for some people to shave. So the one who shaved it all would be more emphatic in his worship.
Source قناة «فضيلة الشيخ محمد بن صالح العثيمين»، [3561] سبب دعاء النبي ﷺ للمحلقين ثلاثاً والمقصرين مرة واحدة - تعليقات على الكافي لابن عثيمين — youtube.com

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

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