This is another post in my series, Reader’s Guide to Amos. It works(or at least, I’d like it to) as something between a commentary and a Bible Study. Go read the text. Keep that window open. Read through it once to get a broad view of what is happening. Then come back and read through my notes. I’d suggest going back to the text one more time, read through it and when you get to a word or idea you are unsure of, come back and see if there is something in my Reader’s Guide that helps. You can read my original series introduction and the original posts that cover the text up to this point.

5:1-17
There is a distinct pattern here in the structure and arrangement of these verses (WBC.)
5:1-3 – Lamentation
5:4-6 – Exhortation
5:7 – Accusation
5:8-9 – Hymn
5:10-13 – Accusation & Judgment
5:14-15 – Exhortation
5:16-17 – Lamentation

1 – Lament is a funeral song, sung over the dead
2 – Fallen, as in on the field of battle and no one is there to help (WBC). Virgin here connotes youth and purity (NAC).
3 – ‘went out’ as in marching out, as in sent out an army. Few will return. Those sent out, are marching to their deaths.
4-6 – Bethal (mentioned thrice), Gilgal (mentioned twice) and Beersheba (once) are all centers of false worship. Only Jerusalem is the center for worship. The frequency of mention, is connected/related/corralled with their familiarity/importance to the audience (NAC)
7 – Wormwood – a bitter tasting plant used proverbially as poison
Thrown down – thrown away, thrown out
You have the two pillars of the covenant requirement here with Justice and Righteousness. The sweet words and deeds of justice are being turned to bitterness (Tyndale). Righteousness is being tossed out with the trash.
8-9 Another hymn, similar to 4:13. Pleiades and Orion are well known constellations in the ANE.
10-13 ‘Him who reproves’ is either the Judge or the Elder on the Jury whom renders the verdict.
‘At the gate – where court was held/lawsuits were handled
As punishment, those who exploit the poor to become rich will not enjoy their material wealth.
Prudent – has the meaning of insight or understanding (NAC), so it is likely the judges/elders at the court who oppress the poor.
‘In such a time’ in the future exile, which is the ‘evil time’.
Verse 13, despite starting with ‘therefore’, which usually indicated judgment is likely a proverb, can be understood as – in time, those who silenced the poor, will themselves be silenced.
14-15 – Seeking is more than looking for, but actively working so that good prevails over evil (NAC)
Establish is to set up justice (contrasted with casting down righteousness in v7 (Tyndale)) in the court
Do these things and Yahweh may save a few, the remnant of Israel
16-17 – ‘skilled in lamentation’ – Israel had professional mourners, so the mourning, wailing (the woe) will be so great that even the famers and those in the vineyards will lament and wail and mourn.
‘I will pass through’ recalls Exodus. The lord will pass through, he is there for judgement and as with Egypt, he will also be the cause of the mourning (due to the judgement).

5:18-27
This is a woe oracle with two parts. First, the misunderstanding of the day of the Lord, and second, the rejection of Israel’s worship. See here for notes on Day of the Lord
18 – They are expected the Day of Lord to be a victory for them, but as God brings his judgment for their breaking of the covenant, the Day, will be a victory against them.
19 – There will be no escaping the destruction (NAC). It would be like fleeing from a lion, only to run into a bear, which ever direction you turn, you will die. Or, entering your house, expecting you are safe, but to be bitten and die.
20 – The Day will bring darkness, not light. Only darkness, not even a hint of light. “The Northern Kingdom was awaiting devastation, no deliverance” – WBC
21-24 – The site of this oracle is likely Bethel, where there were cultic festivals. They practiced much religiousty, following the practice of religion, but they did not have justice or righteousness. So, they had actions, but not right hearts and minds. This is why they are judged. You really need to take time and ponder the strength in which this woe comes. The amount of rejection and admonition should be crushing.
25- Rhetorical question. The time in the wilderness was also considered the apex of Israelites devotion and worship of Yahweh (WBC). There weren’t many sacrifices then, there wasn’t religiosusity and false devotion
26 – Assyrian deities. In contrast to the wilderness era of devotion, they take up other gods and idolatry.
27 – Punishment for the idolatry. You will be sent out past Damascus. Damascus was north, northeast of Israel. Following this path, leads to the roads of Assyria. Decades later, the Assyrians would conquer Israel and exile them.

Commentary Sources:
Amos, Obadiah, Jonah: An Exegetical and Theological Exposition of Holy Scripture (The New American Commentary)
Joel and Amos (Tyndale Old Testament Commentaries)
Hosea-Jonah, Volume 31 (Word Biblical Commentary)