When: the Greek clearly conveys uncertainty about whether Timothy will visit Corinth. Good News Bible‘s “If Timothy comes” expresses this correctly. There is no basis for Revised Standard Version‘s When.

Comes: Good News Bible‘s “your way” is implied. One can also say “If Timothy arrives in Corinth.” Paul speaks in very similar language in 2.3 of his own arrival in Corinth. Several translations therefore have “arrives.”

Put him at ease among you: this rendering seems to weaken the meaning (so also Good News Bible). New Jerusalem Bible has “make sure that he has nothing to fear from you,” and Translator’s New Testament “see that he has nothing to fear while he is with you.” These latter translations are closer to the meaning of the Greek.

The phrase as I am may be expanded to “as I work for the Lord.”

Quoted with permission from Ellingworth, Paul and Hatton, Howard A. A Handbook on Paul’s First Letter to the Corinthians, 2nd edition. (UBS Handbook Series). New York: UBS, 1985/1994. For this and other handbooks for translators see here .