The foundational pesukim establish that the cloud and fire accompanied Bnei Yisrael throughout the midbar: Bamidbar 9:15-17 describes the cloud covering the Mishkan by day and appearing as fire by night, determining when the people journeyed and when they encamped, while Devarim 31:15 records the pillar of cloud resting at the entrance of the Tent, and Tehillim 78:14 summarizes that God led them with a cloud by day and the light of fire all night.
On Shemot 13:21, Rashi (Shemot 13:21) explains that the pillar of cloud functioned as God's emissary to direct the path, not to provide light, while the Ramban (Shemot 13:21) adds that God Himself dwelled within the cloud by day and within the pillar of fire by night, drawing on the idea that 'Hashem' by day parallels His court by night. Ibn Ezra (Shemot 13:21) explains the two pillars were needed because the camp was so large that travel had to continue through parts of both day and night, and the Sforno (Shemot 13:21) locates the start of this divine accompaniment from Sukkot, just beyond Egypt's border. Or HaChaim (Shemot 13:21) distinguishes a protective daytime cloud shielding from heat from the separate guiding cloud that leveled the terrain, citing Sifrei Devarim 39:7's broader theme of clouds surrounding the land as support for the double-cloud image, and Rabbeinu Bahya, Shemot 13:21 and Rabbeinu Bachya similarly read the two pillars as signs of the Divine Name's constant presence, serving as both guide and protection against Egypt. Meiri likewise describes the cloud as long enough to serve partly as shelter and partly to show the way.
Rashi (Bamidbar 9:17) and Rashi (Bamidbar 9:18) detail the mechanics of the cloud's movement — its rising signaled departure, and it would hover over the camp of Yehuda like a canopy until Moshe declared 'Kumah Hashem,' at which point it would disperse to initiate travel — a sequence elaborated by Haamek Davar (Bamidbar 9:17), who describes the stages from the trumpet blasts through the folding of the cloud to the eventual departure, and echoed in Midrash Tanchuma, Bamidbar 12, where Moshe used the cloud's departure as the signal to recite the same verse.
Several Chazal sources describe the clouds of glory as plural and protective: Mekhilta DeRabbi Yishmael, Tractate Vayehi Beshalach 1:20-22 records Rabbi Akiva's view that 'sukkot' in the wilderness refers to clouds of glory, linking this to the ultimate canopy of glory in the end of days, and Sukkah 11b:14-15 preserves the machlokes between Rabbi Eliezer, who held the sukkot were clouds of glory, and Rabbi Akiva, who held they were actual booths. Mekhilta DeRabbi Shimon Ben Yochai 13:21 adds that the pillar of cloud and pillar of fire alternated so that one grew as the other receded, immune to sun or moon, and that seven clouds of glory were given to Israel as they had been given to Avraham. Tzitz Eliezer 14:61 describes these seven clouds as surrounding Israel on every side with the Shechinah among them for forty years, with a pillar of cloud going before them to level the terrain.
Two sources connect the pillars to the splitting of the sea: Malbim (Shemot 14:20) explains that the pillar of cloud darkened the Egyptian camp while the pillar of fire illuminated Israel's side, keeping the two camps apart all night, and Rashi (Shemot 14:24) records that the pillar of cloud turned the seabed to clay while the pillar of fire heated it, causing the Egyptian horses' hooves to come off. תורת חיים בשלח 8 likewise raises the sequence of the divine messenger, the cloud, and the east wind in that episode.
Other sources draw out the symbolic or theological dimension of the pillars: Ibn Ezra (Devarim 4:34) identifies the 'mighty hand' and 'outstretched arm' of the Shemot with the pillar of fire and the pillar of cloud, Mekhilta DeRabbi Shimon Ben Yochai 19:9 likens the cloud of the giving of the Torah to the cloud over Sinai, and Devarim Rabbah 7:10 cites Moshe's rebuke invoking God's guidance of Israel through the midbar. Sulam on Zohar, Beshalach 157 identifies the pillar of cloud with the angel Michael accompanying the Shechinah, and Birkat Asher on Torah, Shemot 13:21:1 likewise names the pillar of cloud and pillar of fire as paired phenomena, while Maamar HaChochmah, Chelek 1 10:3 develops the cloud as the garment through which higher light is revealed below.
Among page sources read in full, Chiddushei Aggadot, Shabbat 23 explains that the pillar of cloud appeared by day while the pillar of fire rose alongside it, cautioning against treating them as two separate authorities, and Beit Yaakov, Pekudei 24 and Beit Yaakov, Pekudei 25 both cite Shemot 40's description of the cloud by day and fire by night over the Mishkan, stressing that the cloud remained even when the Mishkan was dismantled and that this divine light must be awakened to be seen by all Israel.
Tzitz Eliezer 15:64 takes up the fate of these clouds after the sin of the Golden Calf, noting that although the clouds of glory are said to have departed at that point, the pillars themselves may nevertheless have remained with Israel.