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Bamidbar Rabbah 2:7 describes the symbol on Issachar's banner as the sun and the moon.
I have researched the topic of what it is permitted to draw, and it seems that drawing the sun, moon, stars, or planets is universally prohibited. The only exception is made in the Shulhan Aruh for pedagogical purposes.
How could Issachar fly such a banner? Was it a reference for Kiddush Levanah and Birkat Hachama, since they knew the times? (v.33)
Sources please!
Tzitz Eliezer 9:44:2 says he was asked regarding the flag of Yisaschar, however it is not a question as it was done Al Pi Hadibur - through the word of Hashem.
See the tur yoreh dea 141 for a larger discussion. Pedagogical purposes is not the only exception. For the Rif admittedly it is the only exception but according to the rosh if it is of the public, rather than that of an individual, it is OK. Yissachar's banner was of the public.
There is also a distinction between weaving and non-weaving, with weaving what happened by the flags. But this exclusion of weaving is understood by rabbenu tam and Ramban to not apply to sun, moon, etc., based on a diyuk in the Gemara that asked that Rabban Gamliel was an individual, and they don't give the answer there in the Gemara that his images didn't jut out. Perhaps on behalf of the Rif who holds only the pedagogic exclusion and not the public vs. individual exclusion, we could say he doesn't make the diyuk of Rabbenu Tam and so would permit it by virtue of it being woven.
Bamidbar Rabbah 2:3
Another matter, 'He brought me to the house of wine...' When Gd appeared on Sinai 22 ten thousands of angels descended with him, as it says (Psalms 68) 'The chariot of Gd is twice ten thousand, thousands of angels...' and all of them were made standards, as it says (Song 5) '...eminent (דגול) over ten thousands...' Once Israel saw them with standards they began to desire standards. They said 'if only we be made into standards like them... Gd said to them 'How you desire to make standards! By your lives that I will fulfill your request, as it says (Psalms 20) 'Gd will fulfill all of your requests...' Immediately Gd told them to Israel and said to Moses 'Go. Make them standards as they desire'.
2:6
... and not only that, he made them into standards for His name. Gd said to Moses 'Make them standard in My Name, insomuch as they are my children', as it says (Deuteronomy 14) 'You are children of Hashem your Gd...', 'and they are my legions', as it says (Exodus 7) 'And I shall bring forth My Legions, My nation the children of Israel, from the land of Egypt', and so it says 'The standard of the camp of Judah to the south of their legions', 'And since they are My legions I will make them in to standards for My name'.
So Gd commanded that the standards be made, and even told Israel what they were in 2:3, מיד הודיע הקב"ה אותם לישראל Immediately G-d told them to Israel, seems like he's telling them their standards.
Rabbeinu Becahya says that their banners were based on the Heavenly Banners that they saw at Sinai, which appeared as flames of varying shapes and colors. He also describes the layout and organization of the Tribes as being based on the 'Upper Tribes' of the Shehina. The Camp of Judah, of which Issachar and Zebulun were a part, Represented the Camp of Gabriel on high, which consisted of Gabriel Azrael and Shemayel , and also the face of the lion on the Merkabah chariot. So we see that they weren't making up these signs on their own, and they had a profound significance.
So it seems that since the banners were made at Gd's behest, and they represented real parallels between the Upper and Lower Camps (not just the human imagination) they superseded the general rule. We know the cherubs were exceptional as well, as they evidently contradicted the general principles which prohibitted sculpting such things.
