Heidegger's Bible Handbook: Titus: Time of Writing
5. The time of writing investigated. The opinion of Cappel and Baronius unproven. It appears to have been written between the first and second imprisonment.
That this Epistle was not written in bonds, but with Paul free and released, is argued by the fact that he nowhere makes mention of bonds, and predicts that he is going to winter at Nicopolis, Titus 3:12, that is, as one free, and going here and there at will. And, that it was written before the prior bonds, toward the end of those two years that the Apostle spent in Ephesus, Louis Cappel assert. But Baronius maintains, on 57 and 58 AD, that Paul was carried by sea from Macedonia to Crete, and left Titus there; that thence he came into Grecia, and, since from there he was planning to preach the Gospel in Illyricum, he fetched Titus from Crete, by the Epistle written to him, and advised him, that he should come to him at Nicopolis. This opinion Cappel refutes at length, de Ordine Epistolarum, page 67. But to us both opinions are displeasing, judging that it was not written before the prior bonds. For in Acts Luke nowhere makes mention of the island of Crete, converted by Saint Paul, with Titus as a companion; neither would he pass it over in silence, who did not pass over lesser matters. Therefore, that it was written between the former and the latter bonds, when he as a free man traveled once again through the East, a little after the first Epistle to Timothy, to which it is obviously akin, the Most Learned Ussher more rightly judges, with whom we refer that Epistle to 65 AD.