Answer
Wa `alaykum as-salamu wa rahmatullahi wa barakatuh.
In the Name of Allah, Most Gracious, Most Merciful.
All praise and thanks are due to Allah, and peace and blessings be upon His Messenger.
Dear brother, thanks for your question. May Allah bless those who seek knowledge to dispel the clouds of ignorance.
When a person performs `Umrah during the months of Hajj and then performs Hajj in the same year, thus enjoying the state of removing the ritual consecration in between, this practice is called Tamattu`. But the point here is that one should assume ihram for `Umrah during the specified months of Hajj, not before them.
Answering this question, the Standing Committee for Islamic Research and Ifta’, stated,
First, if a person assumes ihram for `Umrah at the end of Ramadan; performs Tawaf and Sa`i only on the first night of Shawwal; performs Tahallul (removal of the state of ihram) after finishing the `Umrah; and afterwards performs Hajj in the same year, this is not considered Tamattu` because this person’s ihram for `Umrah was not assumed during the months of Hajj.
Second, as for the person who assumes ihram for `Umrah after bypassing the Miqat and then performs `Umrah and travels to Madina and then assumes ihram again at the Miqat for another `Umrah and performs it, this second `Umrah does not cancel the first required damm he or she had to offer to expiate assuming ihram beyond the Miqat for the first `Umrah.
May Allah grant us success, and may peace and blessings be upon our Prophet, Muhammad, and his family and Companions.
Allah Almighty knows best.