Sky Ferreira fans are used to waiting, and they’ve become accustomed to every possible obstacle manifesting itself in their hero’s way. So despite a game performer with an abundance of awesome songs at her disposal, Ferreira’s set Friday at Pitchfork Music Festival was extremely on-brand for not-great reasons. What should have been a triumphant step back into the spotlight was marred by technical difficulties and an abrupt ending. Before it was all over, though, she managed to debut a new track that suggests her long-gestating Masochism will be amazing if it ever comes out.

At first, Ferreira actually seemed to have begun her performance early, but that turned out to be a sound check. Upon its completion, she and her band disappeared backstage around her set’s scheduled 4:15 start time and didn’t return for 20 minutes. When the show did finally kick off, she was beset with monitor and microphone issues: Either we couldn’t hear her, or she couldn’t hear herself, or both. Thus, she engaged in a lot of urgent back-and-forth with the sound people, be it between songs or while the band was blasting away on the power chords and strong backbeats that drive the head-rush revivalism of her 2013 debut Night Time, My Time.

Though well received on impact, Ferreira’s first album has since aged into nothing short of a modern classic — a collection of neon pop-rock tracks that could be the soundtrack to some forgotten ’80s blockbuster. Its tracks lived up to their sterling reputation Friday. Although the sound problems resulted in pitchy vocals on surging mall-pop opener “24 Hours,” she was soon nailing each breathy verse and forceful chorus melody. The crunching euphoria of “Boys,” the aggressively shimmering “Ain’t Your Right,” the sharply cut pop gem “I Blame Myself” — they all sounded superb, even if Ferreira consistently seemed flummoxed by the sound issues and oppressive heat at Chicago’s Union Park. (Just a thought, music festivals: Maybe book her to perform at night time… her time.)

The love for Ferreira’s old songs is such that anticipation for new ones intensifies with each passing year. She’s been teasing a sophomore LP called Masochism for half a decade, but for various reasons outlined in a Pitchfork feature earlier this year, thus far she’s only released one song from it, an eerie string-laden epic called “Downhill Lullaby.” So our collective interest was piqued when she introduced “I Blame Myself” by promising she’d be playing new material at this show — even more so when, after her cover of ‘Til Tuesday’s “Voices Carry” and an electrifying “You’re Not The One,” she announced we’d be treated to something brand new.

But not before the day’s most frustrating snafus yet! Ferreira tried once, twice, three times to perform “Descending,” a winsome new wave jam she says will be out “very soon.” But her mic failed several times, and at least once her band started before she was ready. “It’s like everything that could have possibly gone wrong today has,” she lamented after one of the false starts. Eventually she put the big unveiling on pause to instead perform her misty breakthrough blog hit “Everything Is Embarrassing,” a song she felt more capable of pulling off without a functional monitor.

And then they finally performed “Descending” in full, albeit without resolving the sound issues. It seemed like a winner anyhow, propulsive and jangly under its shiny sheen, with a chorus that evokes the Lemonheads. When it was finally over, she seemed relieved and ready to move on. So imagine her horror when her mic cut out — on purpose this time — and Earl Sweatshirt’s set began across the field. It’s unclear what else she had in store: A live debut for “Downhill Lullaby”? A searing run through “Nobody Asked Me (If I Was Okay)”? Whatever was supposed to happen, it didn’t happen. Instead, Ferreira just stood there stunned and silenced after an hour of chaos. I’d say it was just one of those days if it didn’t feel so much like a microcosm of her career so far.

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