Bnei Yisroel shall camp, each man at his own camp and each man at his own banner, according to their divisions.

Each man at his own banner, with the insignia of their fathers’ houses shall Bnei Yisroel encamp, at a distance around the Tent of Meeting they shall encamp.

...“he brought me to the banquet house,” when the Holy One blessed be He appeared upon Mount Sinai, twenty-two myriads of angels descended with him, as it is stated: “The chariots of God are myriad, thousands upon thousands of companies” (Psalms 68:18), and they were all arranged according to banners, as it is stated: “Preeminent [dagul] among a myriad” (Song of Songs 5:10). When Israel saw that they were all arranged according to banners, they began desiring banners. If only we could be arranged according to banners like them... Immediately, the Holy One blessed be He informed Israel and said to Moses: ‘Go and arrange them according to banners, as they desired.’

“With the insignias” – there were insignias for each and every prince: a banner with a color for each, and every banner like the color of the gems that were on Aaron’s heart, from which the empire learned to make a banner, with colors for each and every banner. For each and every tribe, the prince’s banner was like the color of his stone. Reuben, its stone was a ruby and its banner was dyed red, and mandrakes were depicted on it.

"and mandrakes were depicted on it." Bahya wrote that there was a human figure on the flag of Reuben, alluding to the mandrakes.

Dan, [its stone was] a jacinth, the color of its banner was like a sapphire, and a serpent was depicted on it, based on: “Dan will be a serpent” (Genesis 49:17).

On the flag of Dan was the figure of an eagle. And the chachomim have a tradition that the body was in the form of a serpent, as it is said, "Dan will be a serpent on the road" (Genesis 49:17). And the wings were the wings of an eagle, which signify compassion, as it is said, "Like an eagle who rouses his nest" (Deuteronomy 32:11)...

...and on the flag of Dan was the figure of an eagle, because Jacob compared him to a serpent: "a viper on the path." And it has wings to fly, and it is the most powerful of its kind, and it is the dragon....

He brought me to the banqueting-house, and his banner is raised over me in love.

...Rabbi Yehuda says: “He brought me to the banquet house,” to the great wine cellar, this is Sinai, and Moses taught me Torah that is expounded in forty-nine aspects; “and his banner [vediglo] of love is upon me.”

R. Judah says, “He brought me to the great wine cellar, namely Sinai; and from there He taught me Torah, which is expounded in forty-nine ways to render pure and in forty-nine ways to render impure. And the numerical count (gematria) of (ibid., cont.) “and His standard (wdglw)” is forty-nine.

...Rabbi Yisakhar says: “His banner [vediglo] of love is upon me” – even a person who sits and engages in Torah study and skips [umdaleg] from halakha to halakha and from verse to verse, the Holy One blessed be He says: ‘It is dear to Me,’ – “His banner [vediglo] of love is upon me,” – his skipping [dilugo] is beloved by Me...

[The word shalom ("peace")] also includes the letter Lamed, which is like a structure that floats in the air; its head is raised higher than all the other letters. and it resembles a raised flag, alluding to the fact that peace is a tower of strength and support, and those who uphold it raise a flag and have dominion over all.

And it seems that the matter of flags can be explained based on the concept of physical flags. When a soldier loses their way and searches high and low for a way to return to their camp, if their camp has a flag that can be seen from a distance, they are easily drawn straight back to their camp. Similarly, in the spiritual realm, as it is written, "I have strayed like a lost sheep" (Psalms 119:176), and "for a long time Yisroel has been without the true G-d, and without a teaching priest..." (II Chronicles 15:3). Nevertheless, Jews have the power to instantly circumvent all barriers and be drawn directly to their source, HaKadosh Baruch Hu, in a manner of jumping and leaping, rather than step by step. This is the meaning of the flags that Israel desired, for "degel" is connected to the word "dilug" (leaping), as it is said in the Midrash, " 'his banner is raised over me in love.' - "his skipping over me is love.'"

...And this is the level of a Baal Teshuvah