Did the Prophet (peace and blessings be upon him) ever pray with his head uncovered?

Abu Ishaq: Regarding the Prophet (peace and blessings be upon him), did he ever pray with his head uncovered?

The Shaykh : I cannot say that he did or did not, but I can say that he prayed often. I cannot say that he did or did not because your question is absolute in its wording, but the intention of the speaker is qualified. If you intend...
Abu Ishaq: It is like that, meaning...

The Shaykh : I understand, and therefore I say the wording is such and the intention is such. The intention of the question is: Did he ever pray with his head uncovered while not in the state of ihram? That is, in the normal state. With this qualification, I cannot say that he did or did not, because we have no text that affirms or denies it, except for a hadith narrated by Abu...The Shaykh : ...in the book on the character of the Prophet (peace and blessings be upon him), with a very weak chain of narration. So if this text were authentic, we could say that he sometimes prayed with his head uncovered, covered by his cap. But this hadith is very weak in its chain, so it is considered non-existent. In fact, a hadith with a weak chain is, according to what Imam al-Hafiz Ibn Hibban explicitly stated, considered non-existent. How much more so when its weakness is severe? In that case, we say, as you have heard, that we cannot say he did or did not. However, in the case of ihram for Hajj or 'Umrah, this is a known and clear matter.
But here is something unclear: Many supporters of the Sunnah among you, and supporters of innovation in some of the Maghreb countries—Glory be to my Lord—argue that it is at least not recommended to cover the head in prayer, by analogy with the one in ihram for Hajj or 'Umrah. It is not strange for such logic to come from some innovators, especially that Ghumari who has a small booklet in which he titled a treatise "Unveiling the Confusion Regarding Praying with the Head Uncovered." It is a very small treatise in which he responds to some educated youth—as he claims—who told him that it is a matter of etiquette for a Muslim to pray with his head covered. He gave the Shaykh an example: if one of us wants to meet one of these leaders, does he enter with his head uncovered, or does he show etiquette and adorn himself with the best adornment? The man’s answer was that this issue varies according to customs. In some countries, it is etiquette to uncover the head, and in some countries, to cover the head. So the issue does not have a fixed rule, but rather it is according to custom. That is what he says.
Then he mentioned that those who hold that it is etiquette to cover the head argue with the previous hadith—the hadith of Ibn Abbas— If it were etiquette to cover, he would not have uncovered it. He overlooks explaining the severe weakness, or perhaps he is unaware of his intention, that there is this severe weakness which does not justify mentioning it without explaining this weakness. Then he does not stop there but mentions this strange and odd analogy: if it were etiquette to cover the head in prayer, Allah would have made it clear to the Messenger in Hajj—Glory be to Allah—a strange and exposed fallacy. I am pleased, on this occasion, with what I had read in the treatise on the hijab of women by Shaykh al-Islam Ibn Taymiyyah. He mentioned there a report that, to this day, I have not found with a chain of narration, stating that Ibn Umar (may Allah be pleased with him): meaning: the rulers—.
This is like a report between Nafi' and his master Ibn Umar, which he mentioned but did not attribute, and I have not found it. But I traced a hadith in the authentic Sunan of Abu Dawud—I think it is in the Sunan of al-Bayhaqi with a sound chain to the Prophet (peace and blessings be upon him)—he said:
This elevated phrase in the hadith of Ibn Umar (may Allah be pleased with him) can be considered a corroborating narration for the report of Ibn Umar that Ibn Taymiyyah (may Allah have mercy on him) mentioned in that treatise. His saying (peace and blessings be upon him): undoubtedly, by its generality, implies that when a Muslim stands to converse with his Lord, he should be in the best state, as in the noble verse: Although it was revealed on the occasion that some of the Arabs in the pre-Islamic age of ignorance used to circumambulate naked, including some of the women, so Allah revealed this verse: meaning, cover your private parts. But as you know from the scholars' rule that "the consideration is for the generality of the wording, not the specificity of the cause," especially when the generality comes in an elevated hadith, then it is recommended that the Muslim enter prayer with his head covered, not uncovered. Because this uncovering is a recent phenomenon in the Islamic world; it entered them when the colonizing disbeliever entered them, bringing with him many of his customs and traditions. Those who have no knowledge or no eagerness to adhere to Islamic etiquette adopted and imitated them in this, until uncovering became dominant over covering in some countries. But there are still other Islamic countries—especially the non-Arabs, those whom some nationalists influence—who still preserve these etiquettes.
And therefore, it should not be said, as that man said,The Shaykh : that the issue varies according to customs. The issue varies according to custom only if this custom—meaning the custom of uncovering—were an Islamic custom. But since it is a Western custom, we must fight it and keep people away from it, even outside of prayer. How much more so in prayer?

The questioner : If you please, O honorable...The Shaykh : ...Imam Ahmad—I do not know, I mean—I have not come across his opinion because I have not read that he dislikes leading...

The Shaykh : My lord, the issue really returns to what we mentioned earlier, that there are general Islamic customs and etiquettes such that if a Muslim neglects them, he is considered to have lost his dignity. If he has lost his dignity, his testimony is not accepted. From this perspective, some scholars say what I mentioned earlier. It is not necessary, because I am looking now at the 'awrah of the Muslim, from the navel to the knee. But if one of them—especially if he is a pious Shaykh—goes out just to show people that the 'awrah is only from here to here.

The questioner : A bad appearance.

The Shaykh : So people call him crazy, and this is undoubtedly a loss of dignity. And this is not permissible, even though the original ruling is permissibility. Therefore, the loss of dignity does not occur merely by committing a forbidden act, no, not even by doing something unusual in appearance in front of people. From this angle, they considered the one who walks with his head uncovered to be—as the Turks say—lacking in etiquette, meaning lacking in manners. So he is lacking in manners, so he has lost his dignity, so his testimony is invalid.

The questioner : And the reality is that it is a confirmation of what you graciously mentioned, meaning a truth that is felt in the hearts. When I enter a mosque and see some of the students of Shari'ah who lead the prayer, leading it with their heads uncovered, the soul does not feel at ease praying behind them.

The Shaykh : Allah is the helper. Well, please go ahead.

The questioner : I traced the report

The Shaykh : The cap.

The questioner : The cap in Tamam al-Mana to Ibn Asakir. Does this mean it is from the same path?

The Shaykh : Yes, from the same path.