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Islamic researcher, graduated from Al-Azhar University, Islamic Studies in the English language. I also studied at Temple University in the US.
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In a Nutshell:
Ibn Mas'ud (ra) encountered the Messenger (saw) whilst tending his sheep with the Messenger (saw) performing a miracle in front of ibn Mas'ud (ra). Later, ibn Mas'ud (ra) went to the Messenger (saw) and asked him about these words and accepted Islam.


Background

The Messenger's (saw) call from the outset, like previous Messengers, focused on calling his nation to accept Islam and organise their communty in accordance with it.

Allah asked him to focus on the tribal elites and leaders, those whom society trusted, happy to follow them even if they transitioned to a new collective way of life.

He thus did not proactively call individuals, who could personally agree with him, whilst society still continued with their existing trajectory. His mission was to change society, its structures and institutions, establish a civilisation, not change the faith of some individuals in a missionary sense, whilst society remained the same.

Early companions (ra) would hear rumours of his call and approach him enquiring about Islam and subsequently convert.

One of these was Abdullah ibn Mas'ud (ra).

Abdullah Ibn Mas'ud's (ra) Conversion

Abdullah ibn Mas'ud (ra) was a poor young man from Banu Makhzum who had not yet reached the age of puberty. One day, he was pasturing his sheep for the Meccan elite Uqbah ibn Abi Ma'eet when the Messenger (saw) and Abu Bakr (ra) passed by. He asked him for milk, but ibn Mas'ud refused because the sheep were not his.

The Messenger (saw) asked him to bring a sterile sheep previously unmilked and ibn Mas'ud accepted. The Messenger (saw) recited some prayers and verses and it brought forth a great amount of milk.

The narrations don't mention if the Messenger (saw) presented Islam to him or not, nor is any mention made of actions relating to a conversion. Rather after a while, ibn Mas'ud (ra) went to the Messenger (saw) and asked him to teach him these words and it is assumed after this he accepted Islam and learned the Qur'an from the Messenger (saw).

Ibn Mas'ud (ra) narrated what happened when he brought a sterile sheep to the Messenger (saw):

فَأَتَيْتُهُمَا بِهَا فَاعْتَقَلَهَا أَبُو بَكْرٍ وَأَخَذَ رَسُولُ اللَّهِ صَلَّى اللَّهُ عَلَيْهِ وَسَلَّمَ الضَّرْعَ وَدَعَا، فَحَفَلَ الضَّرْعُ، وَأَتَاهُ أَبُو بَكْرٍ بِصَخْرَةٍ مُتَقَعِّرَةٍ فَحَلَبَ فِيهَا، ثُمَّ شَرِبَ هُوَ وَأَبُو بَكْرٍ ثُمَّ سَقَيَانِي ثُمَّ قَالَ لِلضَّرْعِ: اقْلِصْ. فَقَلَصَ.
فَلَمَّا كَانَ بَعْدُ أَتَيْتُ رَسُولِ اللَّهِ صَلَّى اللَّهُ عَلَيْهِ وَسَلَّمَ فَقُلْتُ: عَلِّمْنِي مِنْ هَذَا الْقَوْلِ الطَّيِّبِ، يَعْنِي الْقُرْآنَ، فَقَالَ: " إِنَّكَ غُلَامٌ مُعَلَّمٌ " فَأَخَذْتُ مِنْ فِيهِ سَبْعِينَ سُورَةً مَا يُنَازِعُنِي فِيهَا أَحَدٌ.
"I brought it to them. Abu Bakr stopped it from moving and the Messenger (saw) touched the udder and prayed. The udder became filled with milk and Abu Bakr brought a bowl-shaped rock for milk.
They drank and gave me a drink then the Messenger (saw) said to the udder to constrict and it did.
After a while, I went to the Messenger (saw) and said: teach me these good words i.e. the Qur'an. He (the Messenger) said: you are a learned youth." (Ibn Kathir, as-Seera al-Nabawiyah, Vol. 1, pp. 444, Qurtubi, Jawami' al-Seera, Vol. 1, p. 38, Musnad Ahmed Vol. 1, p. 379, ibn Sa'd, al-Tabaqat, Vol. 3, pp. 150-151, Dhahabi, Siyar A'lam al-Nubalaa, Vol. 1, p. 465)

This adds further weight, along with all the known stories of each companon, that the Messenger (saw) at the beginning of the dawa did not proactively call non-influential individuals to Islam, rather he focused on the tribal leaders, elites and influentials who represented their societies.

This does not mean the Messenger (saw) neglected or rejected non-influential individuals who enquired about his message, or accepted the truth of his message - such companions spent time with him learning and practicing what had been revealed in Dar al-Arqam; rather his approach was to win over the influentials and elites of society, who could more readily ensure a transition for all of their followers.

Conclusion

The Messenger (saw) performed a miracle in front of ibn Mas'ud (ra) bringing forth a great amount of milk from a sterile sheep. Later, Abdullah ibn Mas'ud (ra) went to the Messenger (saw) and asked him about these words and subsequently accepted Islam.

References

Ibn Kathir, as-Seera al-Nabawiyah
Qurtubi, Jawami' al-Seera
Ibn Sa'd, al-Tabaqat
Dhahabi, Siyar A'lam al-Nubalaa


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