If you haven't guessed, I really wanted to finish the first Paul book by the 15th, tomorrow. But I keep processing not only the details of what I think but also how to present it. I wrote the piece on Philemon, switched the order of the chapters, did half of Colossians, and finally decided to put all that stuff in the second volume. I really think Philemon in itself fits very nicely from Ephesus early in Paul's stay there (except for that comment about being an old man). But it just seems impossible--at least in writing for a more popular audience--to split up Philemon, Colossians, and Ephesians.
So I am back to chapter 9 again! Now it's titled, "Joy in the Face of Death," and it's about Philippians. I was able, however, to use a modified version of my earlier introduction to the Prison Epistles. In the end, even if you have been suffering through all these posts, you will still have to buy the book to see how it all ended up being shuffled around (and of course for the sex chapter :-).
Ephesus at the End
We just quoted 2 Corinthians 1:8 above, where Paul says he had felt a "sentence of death" hanging over his head in his final days at Ephesus. Acts tells us about a silversmith named Demetrius who made shrines to the goddess Artemis (19:24). The temple of Artemis at Ephesus was one of the seven wonders of the ancient world, and you can still see a few of its pillars if you visit the ruins of the city. Acts says that Demetrius stirred up the guild of idol makers, who began to shout, "Great is Artemis of the Ephesians" until the city was all stirred up. They actually dragged some of Paul's coworkers into the theatre (which you can also still see today).
[insert picture of Ephesus theatre]
Although Acts says nothing of Demetrius bringing charges against Paul, it does mention that the city clerk brought up the possibility (19:38). We wonder if Acts is not in fact hinting at the fact that Demetrius did in fact bring up Paul on charges, and that Paul was imprisoned there at Ephesus awaiting trial for a significant amount of time. And we wonder if it was not during this time that Paul wrote Philippians, one of his most precious letters--and one in which he seems most humbled by his circumstances. Is it any surprise that, when Paul passed back through Asia, he did not stop at Ephesus, but met with its elders south of the city, in Miletus (Acts 20:16)? They come to him, and he avoids the city.
The tone of Philippians fits such an uncertain time. "For to me, living is Christ and dying is gain. If I am to live in the flesh, that means fruitful labor for me; and I do not know which I prefer. I am hard pressed between the two: my desire is to depart and be with Christ, for that is far better; but to remain in the flesh is more necessary for you" (1:21-24). Does this mood not fit what Paul says of his final days in Ephesus: "We do not want you to be unaware, brothers and sisters, of the affliction we experienced in Asia; for we were so utterly, unbearably crushed that we despaired of life itself. Indeed, we felt that we had received the sentence of death so that we would rely not on ourselves but on God who raises the dead" (2 Cor. 1:8-9)?
The logistics of Philippians also fit Ephesus better than Rome. For example, Philippians implies that news has gone back and forth between Rome and Ephesus at least four times between Paul's arrest and his writing of the letter. 1) News reached the Philippians of Paul's imprisonment. 2) They sent resources for him by way of a man named Epaphroditus. 3) Epaphroditus became ill and news of his sickness reached the Philippians. 4) News of the Philippians reaction at the illness of Epaphroditus travelled back to Paul. Certainly Paul was imprisoned long enough at Rome for news to travel back and forth this many times, even though each trip would take well over month, probably closer to two. But this back and forth would happen much more naturally between Philippi and Ephesus, perhaps only a little more than a week each way.
Paul also expresses confidence that he will ultimately be released (Phil. 1:25) and expects then to visit Philippi (2:24). He plans to send Timothy ahead with news of the outcome of his trial (2:23). Then when Timothy returns he hopes that he himself might come (2:19, 24). This is again quite a distance to wait for Timothy to get to Philippi and back from Rome. It makes much more sense from Ephesus.
Indeed, Acts does record Paul going to Philippi after leaving Ephesus. Meanwhile, Romans 15:23 tells us that Paul had no intention of ministering any more in the east when he left the region. He had his sights set on ministering even further west, in Spain (15:24). So if Paul was writing Philippians from Rome and thinking of going back east, he had changed his plans significantly from when he left the area. 
Mention of the imperial guard (1:13) and of Caesar's household (4:22) have easily given the impression that Paul was writing from Rome. But Ephesus was the capital of the Roman province of Asia and had a Roman proconsul seated there. He would also have imperial soldiers, and of course the entire administration of the Roman empire everywhere was part of Caesar's household, since a household included servants and all who served a "house."  So while these agents of Caesar would certainly be present in Rome, they were also present in Ephesus.
So while Paul could have written Philippians while imprisoned at Rome, Ephesus seems to fit the particulars of the letter as well or better. The main reason not to adopt this scenario remains one's sense of how much creativity and selection Acts employs. A quick comparison of Luke with Mark probably suffices to show Luke was not simply a passive chronographer. 
We thus suggest that at the end of Paul's stay at Ephesus, one of the metalworkers of the city likely brought charges against him, resulting in a prolonged imprisonment waiting to appear before the Roman proconsul. During that time he received support from the Philippian church by way of a man named Epaphroditus, who himself became deathly ill, but managed to recover. Paul writes Philippians in anticipation of his release, and promises to send Timothy with the news, as soon as Paul knows it.
 The same of course can be said of Philemon, where Paul tells Philemon to prepare a guest room for him (Phlm 22). If Philemon were written from Rome, it would also imply a significant change of trajectory for Paul.
 Thus we remember that Jesus was taken to the "praetorium" of Pilate in Jerusalem, the same word used in 1:13 is used in Mark 15:16.
 Or even a quick comparison of Luke 24 with Acts 1, which covers the same period.