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For even in Thessalonica you sent gifts for my needs once and again. (Philippians 4:16)
Paul entered Thessalonica after leaving Philippi, and the Philippian believers’ gifts to him began immediately and continued consistently (several times). The Greek literally reads “and once and twice” (kai hapax kai dis).
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For even in Thessalonica. Paul had remained there long enough to set up a thriving church. He faced much opposition and persecution. Therefore, we can understand the necessity that others should have taken care of his needs.
Acts 17:1-3 Updated American Standard Version (UASV)
Paul and Silas in Thessalonica
17 Now when they had passed through Amphipolis and Apollonia, they came to Thessalonica, where there was a synagogue of the Jews. 2 And according to Paul’s custom, he went to them, and for three Sabbaths reasoned with them from the Scriptures, 3 explaining and proving that it was necessary that the Christ had to suffer and rise again from the dead, and saying, “This Jesus whom I am proclaiming to you is the Christ.”
Thessalonica. Albert Barnes writes, “This was a seaport of the second part of Macedonia. It is situated at the head of the Bay Thermaicus. It was made the capital of the second division of Macedonia by Æmilius Paulus, when he divided the country into four districts. It was formerly called Therma, but afterward received the name of Thessalonica, either from Cassander, in honour of his wife Thessalonica, the daughter of Philip, or in honour of a victory which Philip obtained over the armies of Thessaly. It was inhabited by Greeks, Romans, and Jews. It is now called Saloniki, and, from its situation, must always be a place of commercial importance. It is situated on the inner bend of the Thermaic Gulf, half-way between the Adriatic and the Hellespont, on the sea margin of a vast plain, watered by several rivers, and was evidently designed for a commercial emporium. It has a population at present of sixty or seventy thousand, about half of whom are Jews. They are said to have thirty-six synagogues, “none of them remarkable for their neatness or elegance of style.” In this place a church was collected, to which Paul afterward addressed the two epistles to the Thessalonians. Where was a synagogue. Greek, where was the synagogue (ἡ συναγωγὴ) of the Jews. It has been remarked by Grotius and Kuinoel that the article used here is emphatic and denotes that there was probably no synagague at Amphipolis and Apollonia. This was the reason why they passed through those places without making any delay.” John McRay, “When the Apostle Paul visited the city, it was larger than Philippi and reflected a predominantly Roman culture. Thessalonica was a free city, having no Roman garrison within its walls and maintaining the privilege of minting its own coins. Like Corinth, it had a cosmopolitan population due to the commercial prowess of the city. The recent discovery of a marble inscription, written partly in Greek and partly in a Samaritan form of Hebrew and Aramaic, testifies to the presence of Samaritans in Thessalonica. The book of Acts testifies to the presence of a Jewish synagogue there (17:1).”
“He … Reasoned with Them from the Scriptures” (Acts 17:1-3)
The above account tells us that Paul came to Thessalonica, where he preached in the synagogue for three Sabbaths. This does not mean that Paul only stayed in Thessalonica for three weeks. There is no information on how long Paul waited to go to the synagogue after he first arrived. We also know that Paul and his traveling companions worked to provide for themselves while there. (1 Thess. 2:9; 2 Thess. 3:7, 8) Then, we also know that Paul had received supplies two times from the brothers in Philippi. (Phil. 4:16) So Paul’s ministry in Thessalonica was likely a good bit longer than three weeks.
Paul, a man of boldness, preached to those assembled in the synagogue. According to his custom, “he went to them, and for three Sabbaths reasoned with them from the Scriptures, explaining and proving that it was necessary that the Christ had to suffer and rise again from the dead, and saying, ‘This Jesus whom I am proclaiming to you is the Christ.’” (Acts 17:2-3) We notice here that Paul was not causing emotional turmoil amongst his listeners. Rather, he challenged their minds. Paul’s audience in the synagogue was familiar with the Scriptures. What they were missing was insight into those Scriptures. Therefore, Paul reasoned, explained, and proved that Jesus Christ was the long-awaited Messiah from the Scriptures.
 Albert Barnes, Notes on the New Testament: Acts, ed. Robert Frew (London: Blackie & Son, 1884–1885), 251.
 John McRay, “Thessalonica,” ed. Chad Brand et al., Holman Illustrated Bible Dictionary (Nashville, TN: Holman Bible Publishers, 2003), 1591.