Early in A.D. 628, the Holy Prophet decided to proceed to Mecca to perform the pilgrimage. He was accompanied by companions about fourteen hundred in number. Hadhrat Umar RA  also accompanied the Holy Prophet PBUH. In order to convince the Quraish that the Muslims had no war-like intentions against them, the Holy Prophet PBUH decided that they would carry no arms.

When the Muslims halted at Zul Hulaifah six miles from Madina, Hadhrat Umar RA waited on the Holy Prophet PBUH and submitted that no reliance could be placed on the Quraish and accordingly, it was unsafe to proceed to Mecca without arms. Hadhrat Umar RA urged that for self-defense the Muslims should be armed. The Holy Prophet PBUH  accepted the advice of Hadhrat Umar RA, and some persons were sent to Madina to bring in arms.

When the Quraish of Mecca came to know that the Muslims were coming to Mecca they sent Khalid bin Walid and Ikramah bin Abu Jahl with two hundred horsemen to intercept the Muslims, and prevent their advance to Mecca. Finding the way to Mecca barred the Holy Prophet PBUH consulted his companions as to what course of action they should adopt. The consensus of opinion was that they should go ahead. If they were stopped they would fight; otherwise not.

The Holy Prophet PBUH enquired of his companions whether anyone out of them could lead the Muslims to Mecca by a path other than the main route barred by the enemy. One of the companions volunteered to show an alternative way. He led the Muslims on the way full of rough rocks through the ravines of Mudniya. After a weary march, the Muslims reached Hudaibiya on the lower side of Mecca and within the sacred territory.

The Muslims encamped at Hudaibiya, and here Urwa bin Masud came to see the Holy Prophet PBUH on behalf of the Quraish. He talked in diplomatic language and tried to impress that the Quraish were strong and would not allow the Muslims to visit Mecca. He also insinuated that at the time of crisis, the followers of the Holy Prophet PBUH were likely to leave him. Thereupon the companions of the Holy Prophet PBUH said, “May God curse you; how dare you think that we will abandon the Holy Prophet PBUH. Rest assured we will fight to the last for him”. When Urwa returned to the Quraish, he gave his impressions about the Holy Prophet PBUH and the Muslims in the following terms:

“O people of the Quraish! I have seen kings but by God, I have never seen a king as I have seen Muhammad PBUH amongst his companions. If he makes his ablutions they would not let the water fall on the ground; if a hair of his body falls they pick it up. They will not surrender him for anything in any case, do what you may.”

As among the Quraish, the Adis specialized in diplomatic skill the Holy Prophet PBUH wanted Hadhrat Umar RA to go to the Quraish to negotiate. Hadhrat Umar submitted that he was a person non grata with the Quraish, and his mission was not likely to be successful. He advised that Hadhrat Usman RA who was soft-spoken and was popular with the Quraish should be sent on the mission. The advice was accepted and Usman was accordingly sent to the Quraish to negotiate regarding the Muslim’s entry into Mecca and performing the pilgrimage.

When three days passed away, and Hadhrat Usman RA did not return from Mecca a rumor got afloat that he had been killed by the Quraish. Hadhrat Umar RA donned his arms and accouterments and waited on the Holy Prophet PBUH. He submitted that if the Quraish had killed Hadhrat Usman RA, the Muslims should fight the Meccans to the bitter end. The Holy Prophet PBUH asked all his Companions about 1,400 in number to assemble and take a vow binding themselves to Jihad against the infidels. The Holy Prophet PBUH sat under a tree, and all the Companions took the oath turn by turn. God approved of this measure, and the following verse was revealed to the Holy Prophet: “Verily Allah was pleased with the faithful that they swore allegiance to thee under the tree.”

In view of the pleasure of God, this oath later came to be called ‘the Bait-ul-Rizwan’- the oath that pleased God. A little later Hadhrat Usman RA returned from Mecca along with some emissaries from the Quraish. After some further negotiations, the terms of a pact between the Muslims and the Quraish were hammered out. These terms were:
There was to be a truce between the Muslims and the Quraish for ten years.

1. If any tribe wanted to enter into a treaty with the Muslims it could do so, and whoever wished to enter a covenant with the Quraish was likewise free to do so.

2. If anyone from the Quraish came to the Muslims without the permission of his guardian, he was to be returned to the Quraish. On the other hand, if a Muslim sought refuge with the Quraish, he was not to be delivered to the Muslims.

3. The Muslims were to withdraw that year without performing the pilgrimage. They were free to perform the Hajj the following year when they could stay in Mecca for three days. Prima facie these terms favored the Quraish and Hadhrat Umar RA felt very bitter about them. He waited on the Holy Prophet PBUH and submitted: “O Prophet of God! Are you not the Messenger of God?” “Certainly I am”, said the Holy Prophet PBUH.
“Are not our enemies idolatrous polytheists?” asked Umar RA.
“Undoubtedly they are”, rejoined the Holy Prophet PBUH.
“Why should then we disgrace our religion?” added Umar RA.
The Holy Prophet  said, “I am the Messenger of God, and I do not act in contravention of His commandments.”

This silenced Hadhrat Umar RA, but he felt these terms to be humiliating to the Muslims. He saw Hadhrat Abu Bakr RA and wanted him to persuade the Holy Prophet PBUH to revise the terms. Hadhrat Abu Bakr RA said: “The Holy Prophet knows things better than we do. What the Holy Prophet PBUH has done is in the interests of the Muslims. Have faith in God. Do not be critical and hold fast to the stirrup of the Holy Prophet  PBUH.” Thereafter the pact which came to be known as the Hudaibiya pact was duly signed between the Muslims and the Meccans. On behalf of the Muslims, the pact was among others signed by Hadhrat Umar RA.

After the pact had been signed Suhail’s son Abu Janda RAl who had accepted Islam and was a captive with the Meccans escaped from the captivity and came to seek refuge in the Muslim camp. Suhail followed his son and demanded that by the Hudaibiya pact, his son should be returned to him. Umar advocated that as Abu Jandal did not want to return, it was unfair to force him to return. The Holy Prophet PBUH said that they had entered into a pact with the Meccans and as Muslims, they could not go back upon their word. He allowed Suhail to take away his son. Turning to Abu Jandal the Holy Prophet PBUH said, “Abu Jandal be patient. God in His bounty will Himself devise some way to facilitate your return to the Muslims”. Hadhrat Umar RA went some distance with Abu Jandal and Suhail. He kept goading Abu Jandal with his sword, and the idea was that he should take the sword and kill his father. Abu Jandal was too depressed and confused to follow the clue. When Suhail and his son rode off to Mecca, Hadhrat Umar RA returned to the Muslim camp crestfallen.

The Muslims struck camp and started on the return journey to Madina. Hadhrat Umar RA felt unhappy. He was bitter that in this deal the Quraish had had the upper hand. In this way, Surah Al-Fath was revealed to the Holy Prophet PBUH. “Verily, We have opened wide for thee the gates of victory.” The Holy Prophet PBUH called for Hadhrat Umar RA and told him that God had that day revealed to him that the Hudaibiya pact would lead to the victory of the Muslims. That made Hadhrat Umar RA rejoice. Hadhrat Abu Bakr RA assessed the Treaty of Hudaibiya in the following terms: “No victory of Islam has more importance than the treaty of Hudaibiya. Men are always for hurrying things on, but God lets them ripen. Previously there had subsisted a wall of partition between the Muslims and the rest of the men; they never spoke to each other, and wherever they met they began to fight. Subsequently, hostility died down, and security and mutual confidence took its place. Every man of even moderate intelligence who heard of Islam joined it, and in the twenty-two months in which the truce subsisted the number of conversions was greater than throughout the whole of the previous period, and the faith of Islam diffused itself in all directions among the people.”

Hudaibiya Pact Developments
In the wake of the Hudaibiya pact there took place developments which affected Umar RA personally. At the time of the Hudaibiya pact, it was undertaken that if any person from the Quraish accepted Islam such a person was to be returned to the Quraish. Some men from among the Quraish accepted Islam and sought shelter with the Muslims. Following the terms of the pact, these persons were returned to the Quraish.

Later a crisis developed when some Quraish women accepted Islam against the wishes of their parents and husbands and sought refuge with the Muslims. The Quraish wanted such women to be returned to them. The Holy Prophet PBUH refused to return such women to the Quraish as in the meantime God had revealed:

“Believers, when believing women came to you as refugees, examine them. Allah knows the state of their faith. If you find them to be true believers do not return them to the unbelievers. They are not lawful to the unbelievers, nor are the unbelievers lawful to them. You shall, however, give to their former husbands what they have spent on them. And you will be doing nothing unlawful after you have given them dowries.” [60: 10]

Another verse on the same subject is provided: “Do not marry idolatresses until they embrace the faith. And do not marry your women to idolaters.”

Hadrat Umar RA had three wives, namely:
1. Zainab bint Mazaun Jamiah;
2. Malaika bint Jarul Khuzai; and
3. Qariba bint Abi Umayya Makhzumi.

Out of these three, only Zainab bint Mazaun had accepted Islam and migrated to Madina. The other two ladies did not accept Islam and did not choose to migrate. After the Hudaibiya pact, Hadhrat Umar RA divorced Malaika as well as Qariba. After being divorced by Hadhrat Umar RA, Malaika married Abu Jahm bin Hazifa while Qariba married Abdur Rahman son of Abu Bakr who was still an infidel.

After the Hudaibiya pact, the first Muslim woman who fled from the Quraish and sought refuge with the Muslims was Sabiha bint al-Haris. Her husband did not accept Islam. When the Quraish came to demand the restoration of Sabiha, the Holy Prophet refused to return her to the Quraish saying that the condition in the pact applied to men only and not to women. The Holy Prophet PBUH had Sabiha married to Umar RA.

In Madina, Hadhrat Umar RA married an Ansar lady Asiah bint Sabat Ansari

.On marriage Hadhrat Umar changed her name to Jamila. Hadhrat Umar resided with her at Quba. It is reported that for some years she was Hadhrat Umar’s favorite wife. A few years later, Hadhrat Umar divorced her and shifted to Madina. The reason why Hadhrat Umar divorced her is not known.