After selling more than 5,000 copies of their self-recorded, self-produced 1997 EP, The Union Underground gained the attention of Columbia A&R executive John Weakland.

Six tracks from the band's self-released EP – "Bitter", "Natural High", "The Friend Song", "Drivel", "Until You Crack", and "Trip With Jesus" (originally titled "Supersonic") – were included on An Education in Rebellion.

[5] A large amount of demo material had been recorded prior to their major label debut, which allowed the band to choose the "cream of the crop" for its inclusion.

[6] In promoting ...An Education in Rebellion, The Union Underground began headlining the Road Rage tour, with opening acts Linkin Park and Systematic, prior to the album's release.

AllMusic's Tim Sheridan gave the album 3 out of 5 stars and commented, "While their sonic punch is undeniable, blending guitar skronk with Bryan Scott's snarled vocals, the rebellious posing of songs like 'Revolution Man' comes off as a calculated marketing ploy rather than true agitation.

Scott dryly mocks the allure of the former: 'Dilate, dilate, what’s my drug of choice?/ It’s okay when they pay, they say I got the voice/ Look at this, the motherfucker is a millionaire/ Realize it’s a mask that you wear' and 'Never forget your lies/ Hypocrisize, five million might change your mind.'

He sneers at the latter and romanticizes drug abuse in rock just as much: 'It’s such a shame that it is this way/ I’m a junkie, god is gay/ Hate to bleed but it heals my pain' and 'Say that you never wanna get high, man/ There’s nothing better, give it a try, man'.