The Greek syntax is broken in this verse, and scribes made various attempts to improve the grammar of this verse, but the meaning is clear: Paul had second thoughts about having written the letter, when he learned that it caused the Corinthians some temporary grief, but now he was glad that he wrote it.

The logical sequence of thoughts may be explained as follows: For in the Greek does not express reason but introduces a further statement of the previous clause “I rejoiced still more,” that is, I do not regret [writing the letter]. Then he introduces his own mixed feelings on the subject, for in fact I did regret it, since, after all, the letter made the people in Corinth feel sad for a while, and he didn’t really feel happy about that. But in general, even if I made you sorry … I do not regret it. Most translators may have to rearrange this sequence of thoughts in a logical order that will be clear to those who hear it read in the receptor language.

Even if: some interpreters do not think that there is any doubt about whether or not Paul had grieved the Corinthians by his previous letter. For this reason New Jerusalem Bible translates “though I did distress you…,” and Contemporary English Version has “even though my letter hurt your feelings” (and similarly Anchor Bible).

Made you sorry may be translated as “hurt your feelings” (Contemporary English Version), although it may be unwise or even impossible to render this English idiom directly in other languages. Other models are “upset you” (Phillips) or “caused you distress.”

With my letter is literally “with the letter.” King James Version incorrectly says “with a letter.” Since the Greek has the definite article, it is clear that Paul is referring to a specific letter that he wrote (see 2.3). So Revised Standard Version appropriately adds the word my, and Good News Translation correctly says “that letter of mine.” Revised English Bible makes explicit that this letter was “sent” to the Corinthians: “by the letter I sent.”

The verb translated made … sorry at the beginning of this verse and grieved toward the end are actually the same in Greek and are thus translated identically in Good News Translation, “made you sad.” The verb rendered regret (positively and negatively) in Revised Standard Version has to do with a general feeling of remorse and is clearly distinguished from the stronger verb translated “repent” in the following verse. It involves sorrow for having committed some act. In Matt 27.3 Judas is said to feel regret (using this verb) but not repentance.

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 .