Al-Mundhiri records in his book al-Targhib wal-Tarhib:

الترغيب في البكاء من خشية الله تعالى

Encouragement to weep from fear of Allah Almighty.

Source: al-Targhīb wal-Tarhīb 4/113

Abu Huraira reported: The Prophet, peace and blessings be upon him, said:

سَبْعَةٌ يُظِلُّهُمْ اللَّهُ فِي ظِلِّهِ يَوْمَ لَا ظِلَّ إِلَّا ظِلُّهُ الْإِمَامُ الْعَادِلُ وَشَابٌّ نَشَأَ بِعِبَادَةِ اللَّهِ وَرَجُلٌ قَلْبُهُ مُعَلَّقٌ فِي الْمَسَاجِدِ وَرَجُلَانِ تَحَابَّا فِي اللَّهِ اجْتَمَعَا عَلَيْهِ وَتَفَرَّقَا عَلَيْهِ وَرَجُلٌ دَعَتْهُ امْرَأَةٌ ذَاتُ مَنْصِبٍ وَجَمَالٍ فَقَالَ إِنِّي أَخَافُ اللَّهَ وَرَجُلٌ تَصَدَّقَ بِصَدَقَةٍ فَأَخْفَاهَا حَتَّى لَا تَعْلَمَ يَمِينُهُ مَا تُنْفِقُ شِمَالُهُ وَرَجُلٌ ذَكَرَ اللَّهَ خَالِيًا فَفَاضَتْ عَيْنَاهُ

There are seven whom Allah will shade on a day when there is no shade but His. They are a just ruler, a youth who grew up in the worship of Allah, one whose heart is attached to the mosques, two who love each other, meet each other, and depart from each other for the sake of Allah, a man who is tempted by a beautiful woman of high status but he rejects her, saying , ‘I fear Allah,’ and one spends in charity and conceals it such that his right hand does not know what his left hand has given, and one who remembered Allah in private and he wept.

Source: Ṣaḥīḥ al-Bukhārī 660, Grade: Muttafaqun Alayhi

Abu Rayhanah reported: The Messenger of Allah, peace and blessings be upon him, said:

حُرِّمَتِ النَّارُ عَلَى عَيْنٍ دَمَعَتْ مِنْ خَشْيَةِ اللهِ حُرِّمَتِ النَّارُ عَلَى عَيْنٍ سَهِرَتْ فِي سَبِيلِ اللهِ حُرِّمَتِ النَّارُ عَلَى عَيْنٍ غَضَّتْ عَنْ مَحَارِمِ اللهِ

The Hellfire is forbidden for the eye weeping from the fear of Allah. The Hellfire is forbidden for the eye vigilant in the way of Allah. The Hellfire is forbidden for the eye that lowers its gaze from what Allah has forbidden.

Source: al-Sunan al-Kubrá lil-Nasā’ī 8818, Grade: Hasan li ghayrihi

Ibn Abbas reported: The Messenger of Allah, peace and blessings be upon him, said:

عَيْنَانِ لاَ تَمَسُّهُمَا النَّارُ عَيْنٌ بَكَتْ مِنْ خَشْيَةِ اللهِ وَعَيْنٌ بَاتَتْ تَحْرُسُ فِي سَبِيلِ اللَّهِ

Two eyes will never touch the Hellfire: an eye weeping from the fear of Allah, and an eye standing guard in the way of Allah.

Source: Sunan al-Tirmidhī 1639, Grade: Sahih li ghayrihi

Abu Huraira reported: The Prophet, peace and blessings be upon him, said, “

حُرِّمَ عَلَى عَيْنَيْنِ أَنْ تَنَالَهُمَا النَّارُ عَيْنٌ بَكَتْ مِنْ خَشْيَةِ اللهِ وَعَيْنٌ بَاتَتْ تَحْرُسُ الْإِسْلَامَ وَأَهْلَهُ مِنْ أَهْلِ الْكُفْرِ

Two eyes are forbidden from being consumed by the Hellfire: an eye weeping from the fear of Allah, and an eye standing guard for Islam and its people against unbelief.

Source: Shu’ab al-Imān 3930, Grade: Sahih li ghayrihi

Abu Huraira reported: The Messenger of Allah, peace and blessings be upon him, said:

لاَ يَلِجُ النَّارَ رَجُلٌ بَكَى مِنْ خَشْيَةِ اللهِ حَتَّى يَعُودَ اللَّبَنُ فِي الضَّرْعِ وَلاَ يَجْتَمِعُ غُبَارٌ فِي سَبِيلِ اللهِ وَدُخَانُ جَهَنَّمَ

A man who weeps from the fear of Allah will never enter Hellfire, unless milk could return to its udder. The dust in the way of Allah will never combine with the smoke of Hell.

Source: Sunan al-Tirmidhī 1633, Grade: Sahih

Anas ibn Malik reported: The Messenger of Allah, peace and blessings be upon him, said:

عَيْنَانِ لَا تَمَسُّهُمَا النَّارُ أَبَدًا عَيْنٌ بَاتَتْ تَكْلُأُ الْمُسْلِمِينَ فِي سَبِيلِ اللَّهِ وَعَيْنٌ بَكَتْ مِنْ خَشْيَةِ اللَّهِ

Two eyes will never be touched by the Hellfire: an eye staying vigilant for the Muslims in the way of Allah, and an eye weeping from the fear of Allah.

Source: Musnad Abī Ya’lá 4346, Grade: Sahih

Mu’awiyah ibn Jaydah reported: The Messenger of Allah, peace and blessings be upon him, said:

ثَلَاثَةٌ لَا تَرَى أَعْيُنُهُمُ النَّارَ عَيْنٌ حَرَسَتْ فِي سَبِيلِ اللهِ وَعَيْنٌ بَكَتْ مِنْ خَشْيَةِ اللهِ وَعَيْنٌ غَضَّتْ عَنْ مَحَارِمِ اللهِ

Three eyes will never see the Hellfire, an eye standing guard in the way of Allah, an eye weeping from the fear of Allah, and an eye lowering its gaze from what Allah has forbidden.

Source: al-Mu’jam al-Kabīr 1003, Grade: Hasan li ghayrihi

Abu Umamah reported: The Prophet, peace and blessings be upon him, said:

لَيْسَ شَيْءٌ أَحَبَّ إِلَى اللهِ مِنْ قَطْرَتَيْنِ وَأَثَرَيْنِ قَطْرَةٌ مِنْ دُمُوعٍ فِي خَشْيَةِ اللهِ وَقَطْرَةُ دَمٍ تُهَرَاقُ فِي سَبِيلِ اللهِ وَأَمَّا الأَثَرَانِ فَأَثَرٌ فِي سَبِيلِ اللهِ وَأَثَرٌ فِي فَرِيضَةٍ مِنْ فَرَائِضِ اللَّهِ

Nothing is more beloved to Allah than two drops and two footsteps: a teardrop from fear of Allah and a drop of blood shed in the way of Allah. As for two footsteps, a footstep in the way of Allah and a footstep in one of the obligations of Allah.

Source: Sunan al-Tirmidhī 1669, Grade: Hasan

Ibn Abi Mulaykah reported: I was sitting with Abdullah ibn Amr, may Allah be pleased with him, by the stone of the Ka’bah and he mentioned a prophetic tradition, then he said:

ابْكُوا فَإِنْ لَمْ تَجِدُوا بُكَاءً فَتَبَاكَوْا وَالَّذِي نَفْسِي بِيَدِهِ لَوْ أَنَّكُمْ تَعْلَمُونَ الْعِلْمَ لَصَرَخَ أَحَدُكُمْ حَتَّى يَنْقَطِعَ صَوْتُهُ وَصَلَّى حَتَّى يَنْكَسِرَ صُلْبُهُ

Weep! If you do not find yourself weeping, then feign weeping. By the one in whose hand is my soul, if you truly knew, one of you would cry out until his voice is hoarse and pray until his back is broken.

Source: al-Zuhd wal-Raqā’iq 1007, Grade: Sahih

Abu Mutarrif reported:

رَأَيْتُ رَسُولَ اللَّهِ صَلَّى اللَّهُ عَلَيْهِ وَسَلَّمَ يُصَلِّي وَفِي صَدْرِهِ أَزِيزٌ كَأَزِيزِ الرَّحَى مِنْ الْبُكَاءِ صَلَّى اللَّهُ عَلَيْهِ وَسَلَّمَ

I saw the Messenger of Allah, peace and blessings be upon him, while he was praying. His chest made a sound like a boiling water pot from his crying.

Source: Sunan Abī Dāwūd 904, Grade: Sahih

Ali reported:

مَا كَانَ فِينَا فَارِسٌ يَوْمَ بَدْرٍ غَيْرَ الْمِقْدَادِ وَلَقَدْ رَأَيْتُنَا وَمَا فِينَا إِلَّا نَائِمٌ إِلَّا رَسُولُ اللَّهِ صَلَّى اللهُ عَلَيْهِ وَسَلَّمَ تَحْتَ شَجَرَةٍ يُصَلِّي، وَيَبْكِي، حَتَّى أَصْبَحَ

None among us was upon a horse on the day of Badr other than Al-Miqdad. We saw, though everyone else was sleeping, the Messenger of Allah, peace and blessings be upon him, under a tree praying and weeping until dawn.

Source: Ṣaḥīḥ Ibn Khuzaymah 899, Grade: Sahih

‘Uqbah ibn ‘Amir reported: I said, “O Messenger of Allah, what will save us?” The Messenger of Allah, peace and blessings be upon him, said:

أَمْسِكْ عَلَيْكَ لِسَانَكَ وَلْيَسَعْكَ بَيْتُكَ وَابْكِ عَلَى خَطِيئَتِكَ

Restrain your tongue, let your house be enough for you, and weep for your sins.

Source: Sunan al-Tirmidhī 2406, Grade: Sahih

Thawban reported: The Prophet, peace and blessings be upon him, said:

طُوبَى لِمَنْ مَلَكَ لِسَانَهُ وَوَسِعَهُ بَيْتُهُ وَبَكَى عَلَى خَطِيئَتِهِ

Blessed is one who controls his tongue, whose house is spacious enough, and who weeps for his sins.

Source: al-Mu’jam al-Awsaṭ 2398, Grade: Hasan