How long was the period from Paul's missionary journeys to his imprisonment?
The period from the beginning of Paul's missionary journeys out of Palestine to his imprisonment was about 25 years. It began around 40 A.D. and ended when he went to prison, probably in 64 or 65 A.D. During this span he constantly appealed to the Jew on the basis of the Old Testament.
Les explains that the years from 40 A.D. until Paul goes to prison, probably in 64 or 65 A.D., cover a period of about 25 years. During that time, beginning with his missionary journeys out of Palestine or the land of Israel, up into Asia Minor, beginning about 40 A.D. and around the city of Antioch up in Syria, Paul was constantly appealing to the Jew on the basis of the Old Testament. Les also notes that I and II Thessalonians were written first, probably about 57 or 58 A.D., even though the Holy Spirit placed them at the end of the New Testament order. Understanding this historical setting helps explain where the Apostle is coming from and why the Holy Spirit does what He does.