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A Christian may receive the Anointing of the Sick multiple times (CCC §1529) - Tolle Lege

Catechism

§1529

Sacraments › … › In Brief

Each time a Christian falls seriously ill, he may receive the Anointing of the Sick, and also when, after he has received it, the illness worsens.

Read in full at Vatican.va

Source: Catechism of the Catholic Church (Vatican.va)