With them, that is, with Titus (8.17) and the unnamed brother (8.18). In some languages it may be better to say “with these two men….” Contemporary English Version goes even further, making a separate sentence of this: “we are also sending someone else with Titus and the other follower.”

We are sending is literally “we sent” (see comments on the verb tense in 8.17).

Our brother is not to be taken in the literal, biological sense. This brother apparently is a Christian who has worked with Paul, so the pronoun our probably does not include the readers. The individual is not identified. Translators need to be clear that this brother is not the same as the person mentioned in verses 18-19. Revised English Bible says “We are sending with them another of our company.” Parola Del Signore: La Bibbia in Lingua Corrente says “I am sending with them another of our brothers,” and Brazil’s Portuguese common language version (Nova Tradução na Linguagem de Hoje) says “With them we are sending another brother.” It may be advisable to add the word “another [brother].”

Though Paul does not state how the brother was tested, it was probably by having always done the tasks that were assigned to him.

Earnest: some languages may speak of “enthusiasm,” “eagerness” or “fervor.” See comments on 8.16.

In the specific context the brother’s great confidence probably refers primarily to his confidence that the Corinthians will contribute generously and willingly to the collection for the Christians in Jerusalem.

Quoted with permission from Omanson, Roger L. and Ellingworth, Paul. A Handbook on Paul’s Second Letter to the Corinthians. (UBS Handbook Series). New York: UBS, 1993. For this and other handbooks for translators see here .