Is it prescribed in Islam to make oneself weep during prayer?
Question

If you cannot weep during prayer, should you make yourself weep?
Praise be to Allah.Weeping during prayer is one of the outcomes of humble submission (khushu‘) in prayer, and Allah, may He be exalted, praises those who are humbly submissive in their prayer, as He says (interpretation of the meaning):
{Certainly will the believers have succeeded,
They who are during their prayer humbly submissive} [Al-Mu’minun 23:1-2].
Ibn Juzayy (may Allah have mercy on him) said: Humble submission (khushu‘) is a state of heart, which results from fear of Allah, awareness that Allah is watching and humility before the greatness of the Lord, may He be glorified and exalted. The impact of that is seen in the limbs, which become still, and also includes focusing on the prayer, not looking around, weeping, and beseeching."(Tafsir ibn Juzayy  2/48).
Hence weeping during prayer stems from fear of Allah, which is something prescribed and required. Allah, may He be exalted, says (interpretation of the meaning):
{And they fall upon their faces weeping, and the Qur’an increases them in humble submission} [Al-Isra’ 17:109].
Al-Qurtubi (may Allah have mercy on him) said: The word {weeping} indicates that it is permissible to weep during prayer out of fear of Allah, may He be exalted, or because of having disobeyed Allah, and that does not interrupt the prayer or detract from it."(Tafsir al-Qurtubi  10/342).
It is soundly narrated from the Prophet (blessings and peace of Allah be upon him) and his companions that they used to weep during prayer out of fear of Allah.
It was narrated that ‘Abdullah ibn ash-Shikhkhir (m ay Allah be pleased with him) said: I came to the Prophet (blessings and peace of Allah be upon him) when he was praying and his sobbing sounded like water boiling in a pot – meaning that he was weeping. Narrated by an-Nasa’i (1214); classed as sahih by al-Albani.
It was narrated from ‘A’ishah, the Mother of the Believers, that the Messenger of Allah (blessings and peace of Allah be upon him) said during his final sickness: “Tell Abu Bakr to lead the people in prayer.” ‘A’ishah said: If Abu Bakr stands in your place, he will not be able to make the people hear him because of his weeping, so tell ‘Umar to lead the people in prayer… Narrated by al-Bukhari (716).
This weeping is one of the outcomes of humble submission (khushu‘), but not weeping does not mean that one has not attained humble submission. Many of the Sahabah (may Allah be pleased with them) described the Prophet’s prayer without mentioning that he wept during it, and he is the foremost of those who fear Allah and submit humbly to Him.
At-Tabari narrated that Ibn ‘Abbas (may Allah be pleased with him) said regarding the verse {They who are during their prayer humbly submissive} [al-Mu’minun 23:2]: They are filled with fear of Allah and are calm. Tafsir at-Tabari (17/10).
Shaykh al-Amin ash-Shinqiti (may Allah have mercy on him) said: The root meaning of the word khushu‘ (translated here as humble submission) is stillness and calmness, and a physical posture that is indicative of humility.
In Islamic terminology, it refers to fear of Allah in the heart, the impact of which is seen in the limbs and physical posture."(Adwa’ al-Bayan  5/825).
Secondly:
The type of weeping that is praiseworthy is that which overcomes a person because of his softheartedness and his humble submission in his prayer, and when he hears the verses of Allah being recited to him.
The one who is not able to weep should not miss out on reflecting [on the meaning of the verses recited] or on humble submission in his heart resulting in stillness of his limbs, because there is no connection between the two. The heart may be humbly submissive, without there being tears in the eyes, or there may be tears in the eyes, but no humble submission in the heart, which is the worst of states, Allah forbid.
Regarding the hadith, “This Qur’an was sent down with sorrow, so when you read it, then weep, and if you do not weep, make yourself weep” (narrated by Ibn Majah, 1337), it is a da‘if (weak) hadith and is not sahih (sound). Al-Busayri said: This isnad includes Abu Rafi‘, whose name is Isma‘il ibn Rafi‘; he is da‘if (weak) and matruk (his hadith is to be rejected). Misbah az-Zujajah fi Zawa’id Ibn Majah (1/157). It was also classed as da‘if by al-Albani.
If we assume that the hadith is sahih, what is meant by making oneself weep is having focus in the heart and making oneself feel sorrow; it does not mean making artificial sounds to resemble weeping. That is a kind of effort that is not allowed; rather some of the scholars have stated that deliberately making sounds that resemble weeping invalidates the prayer.
Al-Fayyumi (may Allah have mercy on him) said: Ibn ‘Abbas said: If a person recites the verse in al-Isra’ in which there is a sajdah (v. 109), do not hasten to prostrate unless you are weeping, and if the eyes of one of you are not weeping, then let him make his heart weep. The way to make oneself weep is to bring sorrow into one’s heart."(Fath al-Qarib al-Mujib ‘ala at-Targhib wa’t-Tarhib 7/121).
Shaykh ‘Abd al-‘Aziz ibn Baz (may Allah have mercy on him) was asked: What is the ruling on making oneself weep? And how sound are the reports that were narrated concerning that?
He replied: In some hadiths it says that if you do not weep, then make yourself weep, but I do not know how sound that is… What appears to be the case is that one should not put effort into making oneself weep; rather if a person finds himself weeping, he should try hard not to disturb others, and his weeping should be quiet; he should avoid disturbing others as much as possible."(Majmu‘ Fatawa wa Maqalat  11/347).
Shaykh Ibn ‘Uthaymin (may Allah have mercy on him) was asked:  What is the ruling on making oneself weep loudly during congregational prayers in the mosque in order to create an atmosphere of humble submission (khushu‘)?
He replied: Making oneself cry artificially – as some people do – is not prescribed in Islamic teachings.
As for that weeping which stems from humble submission in the heart, bringing to mind the greatness of the Lord and fearing Him, this is something that is prescribed, and if a person makes a sound involuntarily, without making himself do that, there is nothing wrong with that.
But pretending to weep is something that is not prescribed and is not appropriate; rather what is required is to reflect on the words of Allah, may He be glorified and exalted, with sincerity and understanding the meaning. Then if a person’s heart softens as a result of that and becomes humbly submissive, and he weeps when punishment is mentioned out of fear of it, and when reward is mentioned out of hope for it, and when the Lord is mentioned out of reverence towards Him, and when the Messenger (blessings and peace of Allah be upon him) and his story are mentioned out of love towards him and longing to meet him, that is a good thing."(Al-Liqa’ ash-Shahri  5/8).
And Allah knows best.