Supplies for 40,000 people were allowed into the towns of Kafra Batna and Saqba on Monday, according to the UN.
It comes days after the UN human rights chief said the plight of civilians trapped there was "an outrage" that might constitute a war crime.
Some 350,000 people have been besieged by pro-government forces since 2013.
The convoy of 49 trucks was carrying "8,000 food parcels and a similar number of bags of flour, medicine, medical supplies, and other nutritional materials", Mona Kurdi, a Syrian Arab Red Crescent spokeswoman, told AFP news agencies.
The last UN aid convoy, carrying aid for 25,000 people, reached the area on 23 September.

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