The Messenger of Allah ﷺ performed two umrahs, one in Dhul Qadah and another in Shawwal.
أن رسول الله ﷺ اعتمر عمرتين: عمرة في ذي القعدة، وعمرة في شوال.
Abu Dawud (1991) narrated it from Abdul-Ala bin Hammad, who said, Dawud bin Abdul-Rahman told us, from Hisham bin Urwa, from his father, from Ayesha, and she related it. Except that her saying "Shawwal" needs to be interpreted, meaning at the end of Shawwal and the beginning of Dhul-Qaidah, as though she means that he ﷺ entered the state of ihram at the end of Shawwal, and his umrah took place in Dhul-Qaidah, as Anas and others said. This is because what is established in the sahih hadiths is that the Prophet ﷺ performed umrah in Dhul-Qaidah. Her saying "two umrahs" means two separate umrahs.Bayhaqi (4/346) narrated it through the hadith of Abdullah bin Muhammad bin Ishaq Fakihi in Makkah, who said, Abu Yahya bin Abu Maysara told us, Saeed bin Mansur told us, Abdul-Aziz bin Muhammad told us, Hisham bin Urwa informed us, from his father, from Ayesha, who said, "The Messenger of Allah ﷺ performed umrah three times, one umrah in Shawwal, and two umrahs in Dhul-Qaidah." She means apart from the umrah that was part of his Hajj.As for what Daraqutni (2293) narrated through the route of Ala bin Zuhayr, from Abdul-Rahman bin Aswad, from his father, from Ayesha, who said, "I went out with the Messenger of Allah ﷺ on an umrah in Ramadan. The Messenger of Allah ﷺ broke his fast while I fasted, and he shortened the prayer while I performed it in full. I said, 'O Messenger of Allah, by my father and mother, you broke your fast while I fasted, and you shortened the prayer while I performed it in full?' He said, "You have done well, Ayesha."This is a mistaken hadith, and some have even claimed it is fabricated, because the Prophet ﷺ never performed umrah in Ramadan at all, and because Ayesha would not have contradicted the Messenger of Allah ﷺ, especially in matters of worship, which are matters of strict textual precedent. Ibn Qayyim mentioned in Zad that the hadith is not sound, and he quoted Sheikh Islam bin Taymiya as saying, "This is a lie attributed to the Messenger of Allah ﷺ."Daraqutni's own ruling on it varied. In the Sunan he said, "Its chain is hasan." But in Ilal (14/258), after pointing out the disagreement over it regarding Ala bin Zuhayr, whether it was transmitted as connected or as mursal, he said, "The mursal version is closer to being correct."However, Hafiz attempted in Fath al-Bari (3/603) to interpret it by saying that her words "in Ramadan" are connected to her words "I went out," meaning that what is intended is the journey for the conquest of Makkah, which did indeed take place in Ramadan, and the Prophet ﷺ did perform umrah that year from Jirana, but it was in Dhul-Qaidah.Daraqutni also narrated it (2294) through another chain leading to Ala bin Zuhayr, but in that chain he did not say "from his father," nor did he mention "Ramadan."