What is "Masa Dumah"?
Radak citing Targum Yonasan: It is the Nevu'ah of the cursed cup [of punishment that it will drink].
What is "Dumah"?
Sanhedrin 94a: It is the angel appointed over Neshamos.
Rashi: It is Edom 1 - "Mi ch'Tzor k'Dumah b'Soch ha'Yam" (Yechezkel 27:32).
Radak: Dumah is from Bnei Yishmael - "u'Mishma v'Dumah u'Masa" (Bereishis 25:14).
Radak (12, according to R. Meir): It is Romi.
Malbim: It is about their fall. It is based on Ovadyah's prophecy (1:5-7. I explained there that scheming advisors enticed it to go [to war] outside its border. When it went out, the enemy came and killed the women and children, and took the property. They are captured to thieves and night plunderers, who enter when the owner is unaware. They plundered more than thieves, who take only what is revealed. They do not have time to search for hidden treasures. They searched also for hidden treasures; they plunder during the day and at night - "Eich Nechpesah Esav Niv'u Matzpunav" (ibid., 6).
What is the meaning of "Elai Korei mi'Se'ir"?
Rashi: Hashem says, the Navi or angel calls to me from the yoke of Malchus Se'ir.
Radak: The Navi says, the voice of Nevu'ah calls to me, for the destroyer of their land will come from Se'ir. He will come soon, and they will put guards on the walls of the city.
Radak (citing R. Yochanan, Yerushalmi Ta'anis 1:1): He calls to me due to Se'ir.
Radak (12, citing his father): In the future, Bnei Se'ir will destroy Dumah. He calls the Navi Shomer and Tzofeh. The Navi speaks as if Bnei Se'ir call him and ask him, what of the night? I.e. what is with the nights and days of Dumah - did the time of its end come, and we will go against them?
Malbim: The Shomer (refer to 21:11:4:5) says that they ask him what happened on the awesome night in Se'ir. "Amar Shomer" (verse 12) applies also to this.
What is the meaning of "Shomer Mah mi'Laylah"?
Sanhedrin 94a: All the Neshamos ask when the redemption will come, ending the night (Galus).
Rashi: Shomer Yisrael (Hashem) - what will be from this night and darkness?
Radak: Amidst great fear, people will rise and go around the city and ask the guards 'what will be of the night?'
Radak (12, citing his father): Refer to 21:11:3:4).
Malbim: This is a metaphor for the destruction of Edom (refer to 21:11:2:2*). They left a Shomer to guard their land. He tells how they ask him what happened in Se'ir. He answers, why do you seek the enemy outside your land? Return to your land, for he is there!
Why does it add "Shomer Mah mi'Leil"?
Radak: The matter is repeated, like people repeat questions. It says mi'Leil (the form when it is Samuch to another noun), even though it is not Samuch, like "El Melech Chizkiyah b'Cheil Kaved" (36:2. It says Cheil, and not Chayil, even though it is not Samuch.)
Radak (citing Yerushalmi Ta'anis 1:1): They asked Yeshayah, what will come to us from the night? He said, wait until I ask. After he asked, he returned to them. They said, Mah Milel (what did He say, the) Shomer [of the worlds, i.e. Hashem]? Yeshayah answered, morning is coming, and also night? They said, also night?! He said, not like you think - rather, morning for Tzadikim and night for Resha'im; morning for Yisrael and night for Kusim.
