How will we reconcile the current Pasuk ("va'Yeired ha'Amaleki ve'ha'Cana'ani ha'Yoshev ba'Har") with Pasuk 25, ?ve?ha?Amaleki ve?ha?Cana'ani Yoshev ba?Eimek??
Da'as Zekenim #1, Moshav Zekenim (in 13:29) and Chizkuni (in Pasuk 45) #1: Perhaps the current Pasuk means that Amalek came in order to make war with Yisrael (because the word "Yoshev" applies to someone who waits in ambush - Da'as Zekenim).
Da'as Zekenim: "ba'Eimek" refers to Hashem's deep counsel 1 - that they turn to the desert and not fight, since they will not succeed, because, even though they were Resha'im, Hashem does not want their downfall.
Chizkuni (in Pasuk 45) #2 and Oznayim la'Torah: Basically, they lived in the valley, between the mountains and Eretz Yisrael. Only some of them went to live in the mountains. 2
As in Vayeishev. Refer to Bereishis, 37:14:2:1.
Chizkuni: "ha'Yoshev ba'Har" (in Pasuk 45) implies that most of them dwelt elsewhere (in the valley). Oznayim la'Torah: And the Torah mentions it here to point out that, since Hashem was not with the Ma'apilim, the few Amalekim and Cana'anim who lived in the mountains were able to defeat them without asking additional Amaleikim and Cana'anim for assistance.
Why does the Pasuk use the double expression "Vayakum Vayaksum"?
Rashi: To teach us that they smote them again and again. 1
Rashi: "Va'yaksum" is from the word "va'Ekos oso Tachon" (and I ground it finely) in Devarim 9:21.
What is the significance of "Chormah", which has not been mentioned until now?
Rashi: They called the place 'Chormah' 1 as a result of this episode.
Targum Yonasan: "Ad Chormah" means 'until they destroyed them'.
An expression of ''Cherem' (which has connotations of destruction).
How will we reconcile the current Pasuk "va'Yered ha'Amaleki ve'ha'Cana'ani ha'Yoshev ba'Har" with the Pasuk in 13:29, where "Amalek Yoshev ve'Eretz ha'Negev ... ve'ha'Cana'ani Yosheval ha'Yam"?
Refer to 14:25:152:2 and note.
How will we reconcile the current Pasuk "va'Yeired ha'Amaleki ... ha'Yoshev ba'Har" with the Pasuk in Devarim, 1:44 "va'Yeitzei ha'Emori ? va'Yaksu eschem be'Se'ir"?
Moshav Zekenim (citing R. Yehudah ha'Chasid): The Emori chased them down the mountain and they fled to Se'ir. They thought that since they (the B'nei Se'ir) are [descended from] their brother (Eisav), they will surely help us. But immediately, the Amaleki (who were also descended from Eisav) and who were in Se'ir, attacked them and chased them until Chormah.
