Does the angels' guarding of Medina and Mecca from the Dajjal include the current expansions, or is it limited to the area during the time of the Prophet, peace and blessings be upon him, or is it limited to the Two Holy Mosques?

The narrations indicate that the prohibition of the Dajjal from entering Mecca and Medina is specific to the boundaries of their sacred precincts (Harams). Angels will stand on the approaches to Mecca and Medina to guard them. The prohibition is not limited to the Sacred Mosque (Masjid al-Haram (definition)) and the Prophet's Mosque (Masjid an-Nabawi) only, but rather includes everything within the boundaries of the two Harams. It does not relate to the places where people lived during the time of prophethood, but rather to the boundaries of the two Harams.