Two more sections prepare the faith community to anoint catechumens:
100. The anointing ordinarily takes place after the homily in a celebration of the word of God (see RCIA 89), and is conferred on each of the catechumens; this rite of anointing may be celebrated several times during the catechumenate. Further, for particular reasons, a priest or a deacon may confer the anointing privately on individual catechumens.
101. The oil used for this rite is to be blessed by the bishop at the chrism Mass, but for pastoral reasons a priest celebrant may bless oil for the rite immediately before the anointing.
Ordinary practice is to yoke this anointing with the proclamation of the Word of God. This is in keeping with the liturgical and scriptural formation of catechumens, and it underscores the link between divine revelation and the celebration of the sacraments.
Roman pragmatism is in evidence here: anoint when there will be benefit, and anoint catechumens in individual/private circumstances when there is need. My interpretation of this directive, along with the similar ones for blessings and exorcism prayers is that when an individual is in particular need, that conferral is not done publicly. When the entire group is anointed, blessed, or prayed over, that liturgy is a public expression of the Church’s liturgy, and representation of the baptized community is not only possible, but desirable.
Section 101 gives a useful option. I would assume that the priest is not to bless already-blessed oil, but use unblessed olive oil for the rite. My sense would be there is little pastoral benefit by not using the parish’s stock of holy oil, but that if it were to run out before the end of Lent, including the blessing would be of benefit.