The album was recorded in 2008 but only released after the masters to her older music had changed ownership in a 2019 purchase of Big Machine by American media proprietor Scooter Braun.

[1] Swift denounced Live from Clear Channel on her social media accounts, calling it "shameless greed in the time of coronavirus" and asked fans not to buy or stream the album.

[7] Music critic Quinn Moreland from Pitchfork wrote that Live from Clear Channel is predictable, failing to match the standards of Swift's past work, and dubbed it a "cheap bootleg" and "a shameless cash-grab".

Moreland commented that the unapproved release looks "eerily similar" to occasions when fake or leaked music appears on streaming services without the concerned artists' authorization—releases where "scammers hold the reins and the real creator never sees a dime".

[8] Live from Clear Channel Stripped 2008 sold 33 copies in the United States and the YouTube audio videos of its eight tracks accumulated 6,000 views combined in its first three days.