Albert Barnes Commentary Isaiah 27:8

"In measure, when thou sendest them away, thou dost contend with them; he hath removed [them] with his rough blast in the day of the east wind." — Isaiah 27:8 (ASV)

In measure ... - This verse in our translation is extremely obscure, and indeed almost unintelligible. It is not much more intelligible in Lowth, or in Noyes, in the Vulgate, or the Septuagint. The various meanings that have been given to the verse can be seen in detail in Vitringa and Rosenmuller. The idea, which I suppose to be the true one, without examining others that have been proposed, is the following, which is as close as possible to a literal translation:

In moderation in sending her (the vineyard)
Away you judged her,
Though carrying her away with a rough tempest
In the time of the east wind.

The word rendered ‘measure’ (סאסאה sa's^e'âh) occurs nowhere else in the Scriptures. It is probably derived from סאה s^e'âh — “a measure;” usually denoting a measure of grain, containing, according to the rabbis, a third part of an ephah, that is, about “a peck.” The word used here is probably a contraction of סאה סאה s^e'âh s^e'âh literally, “measure by measure,” that is, “moderately,” or in moderation. So the rabbis generally understand it.

The idea is ‘small measure by small measure,’ not a large measure at a time; or, in other words, moderately, or in moderation. It refers, I suppose, to the fact that in inflicting judgment on His people, it was not done with intolerable severity. The calamity had not been so overwhelming as to cut them off entirely, but had been tempered with mercy.

When it shooteth forth - This expression does not convey a clear idea. The Hebrew, בשׁלחה b^eshall^echâh - literally, “in sending her forth,” from שׁלח shâlach “to send,” or “to put forth” - refers, I suppose, to the fact that God had sent her, that is, His vineyard, His people, forth to Babylon; He had cast them out of their own land into a distant country, but when it was done, it was tempered with mercy and kindness. In this expression there is indeed a blending of a metaphor with a literal statement, since it appears somewhat incongruous to speak of sending forth a “vineyard;” but such changes in expressions are not uncommon in the Hebrew poets.

Thou wilt debate with it - Or, rather, you have “judged” it; or have punished it. The word ריב riyb means sometimes to debate, contend, or strive; but it means also to take vengeance (1 Samuel 25:39), or to punish; to contend with anyone so as to overcome or punish him. Here it refers to the fact that God “had” had a contention with His people, and had punished them by removing them to Babylon.

He stayeth - (הגה hâgâh). This word means in one form “to meditate,” to think, to speak; in another, “to separate,” as dross from silver, to remove, to take away (Proverbs 25:4–5). Here it means that He “had” removed, or separated His people from their land as with the sweepings of a tempest. The word ‘stayeth’ does not express the true meaning of the passage. It is better expressed in the margin, ‘when He removeth it.’

His rough wind - A tempestuous, boisterous wind, which God sends. Winds are emblematic of judgment, as they sweep away everything before them. Here the word is emblematic of the calamities that came upon Judea by which the nation was removed to Babylon; and the meaning is, that they were removed as in a tempest; they were carried away as if a violent storm had swept over the land.

In the day of the east wind - The east wind in the climate of Judea was usually tempestuous and violent (Job 27:21):
The east wind carrieth him away and he departeth;
And, as a storm, hurleth them out of his place.

(Jeremiah 18:17):
I will scatter them as with an east wind before the enemy.

(Exodus 10:13; Exodus 14:21; Job 38:24; Psalms 78:26; Habakkuk 1:6). This wind was usually hot, noxious, blasting and scorching (Taylor).