Midrasch zu Bereschit 49:14

"But with a lot, etc." (Numbers 26:55). This is [the meaning of] that which is stated (Proverbs 18:18), "The lot puts an end to strife." Since a sign was written for each and every tribe from Yaakov - "Zevulun will dwell on the shore of the seas" (Genesis 49:13); "Yissachar is a boney donkey, etc." (Genesis 49:14); "From Asher, his bread is fat" (Genesis 49:20) - you are only permitted to divide [the land] by the lot. And there were miraculous acts in the lottery: Elazar the Priest wears the Urim and Tumim. And the slips of the lottery were in front of Yehoshua, as stated (Joshua 18:6) "And I will cast the lot for you here in front of the Lord, our God." But before the lot went up, Elazar said with the holy spirit, "The lot of tribe x is coming up, to take place y." And Yehoshua would extend his hand and [it] would come up [into his hand. It was] as it is stated (Joshua 19:51), "These are the inheritances that Elazar the Priest and Yehoshua ben Nun apportioned." And this was [even] more; that the lot would yell out at the time that it went up, "I am the lot of tribe x; I have gone up to it in place y." And from where [do we know] that the lot speaks? As it is stated (Numbers 26:56), "By the mouth of (according to) the lot."

Issachar is a large-boned ass (Gen. 49:14). That is, he bears the yoke of the Torah like an ass that bears its load, while Zebulun brings his wares in ships. Crouching down between the sheepfolds (ibid.). This refers to his disciples, who spread the knowledge of the Torah before the wise throughout the land, as it is said: When ye lie among the sheepfolds, the wings of the dove are covered with silver (Ps. 68:14). For he saw a resting place that it was good (Gen. 49:15). This refers to the Torah, as it is said: I am weary with my groaning, and I find no rest (Jer. 45:3). That it was good alludes to the Torah, since it is said: For I give you good doctrine (Prov. 4:2). And he bowed his shoulders to bear (Gen. 49:15) the yoke of the Torah. And he became a servant under task-work (ibid.). Task-work refers to the law. Whenever the people erred in the law, they would seek a decision from him, as is said: And the princes of Issachar were with Deborah; as was Issachar, so was Barak; into the depth they rushed forth at his feet (Judg. 5:15); for he would search deeply into the law.

9 This is [the meaning of] that which is stated (Proverbs 18:18), "The lot puts an end to strife." Since a sign was written for each and every tribe from Yaakov - "Zevulun will dwell on the shore of the seas" (Genesis 49:13); "Yissachar is a boney donkey, etc." (Genesis 49:14); "From Asher, his bread is fat" (Genesis 49:20) – you are only permitted to divide [the land] by the lot. And there were miraculous acts in the lottery: Elazar the Priest wears the Urim and Tumim. And the slips of the lottery were in front of Yehoshua, as stated (Joshua 18:6) "And I will cast the lot for you here in front of the Lord." But before the lot went up, Elazar said with the holy spirit, “The lot of tribe x is coming up, to take place y.” And Yehoshua would extend his hand and [it] would come up [into his hand. It was] as it is stated (Joshua 19:51), "These are the inheritances that Elazar the Priest and Yehoshua ben Nun apportioned." And this was [even] more; that the lot would yell out at the time that it went up, "I am the lot of tribe x; I have gone up to it in place y." And from where [do we know] that the lot speaks? As it is stated (Numbers 26:56), "By the mouth of (according to) the lot."