The song first appeared as a bonus track on The Late Night Edition of Swift's 2022 studio album Midnights, released by Republic Records, in May 2023.

The edition was only on CD and available for in-person purchase at certain venues of the Eras Tour for a limited time, following which the song was widely shared and available on social media.

Critics and fans alike connected the lyrics to the end of Swift's six-year romance with the English actor Joe Alwyn in early 2023.

The Late Night Edition was only purchasable in-person at merchandise stands of the US leg of the Eras Tour starting in East Rutherford, New Jersey, on May 26–28, 2023.

[6][7] "You're Losing Me" became a "ravenously anticipated" track according to Variety, which reported that "fans were so eager to get their hands" on the CD, causing lines at the stadium a day before the opening of the merchandise store at 12:30 PM EDT on May 26.

[8] The Late Night Edition including "You're Losing Me" was subsequently sold as a digital album for limited-time download on Swift's webstore.

"[21] The main lyrical motif is a word play on the phrase "we're losing him/her", generally used in emergency departments depicted in medical drama shows.

[21] Critics as well as fans have interpreted the lyrics to be about the end of Swift's six-year romantic relationship with the English actor Joe Alwyn, which was a subject of widespread media coverage in April 2023.

In a rave review, Steffanee Wang of Nylon praised the portrayal of heartbreak and sorrow without involving "mic drop moments" or "accusations", the frank tone of its confessional lyrics, the song structure, and Swift's "palpable" restraint in details.

"[23] The Billboard journalist Ashley Iasimone called "You're Losing Me" an "emotionally-charged" ballad that illustrates the "painful, slow ending of a longterm relationship.

"[24] The Variety critic Chris Willman appreciated Swift's decision to release the song as a bonus track, arguing it would have barely fit with the upbeat, sensual production of the standard Midnights.

[8] Callie Ahlgrim of Business Insider christened "You're Losing Me" as the true closing track of Midnights, recontextualizing the album as a body of work "about agonizing and dissociating, not just reminiscing.