Two full contractions get said as one continuous sound, and native speakers never slow down to separate them for you.

Most connected-speech lessons cover a single contraction at a time: "gonna," "wanna," one clean reduction with one clear shape. Real speech rarely stops there. When someone talks through a regret or a hypothetical out loud, two or even three modal contractions often pile up in a row, each one already reduced, then reduced again against its neighbor. The result barely resembles the words it's built from, which is exactly why it trips up even confident listeners.

1. 1

   Expect three words, not one sound

   "Would've should've" isn't a single unfamiliar word, even though it lands on the ear as one. It's two separate contractions, each already a compression of two words, said back to back with no gap between them.

2. 2

   Find the verb, not the sound

   Every stacked contraction is built around modal verbs (would, should, could, might) plus "have," reduced to "-'ve." Listening for the modal verb underneath the blur gives you an anchor the sound alone doesn't.

3. 3

   Let the stress guide you to the count

   Native speakers put slightly more weight on the first modal in a stack than the ones after it. That small stress difference is often the only clue that you're hearing two contractions, not one.

Stacked contractions cluster around a specific kind of sentence: looking back and second-guessing a decision. "I should've could've handled that differently." "You would've should've told me sooner." The grammar is genuinely a little unusual even for native speakers, which is part of why the sound compresses so heavily. Nobody's slowing down to enunciate a sentence they're already embarrassed about.

This is exactly what PopEar is for.

Real speakers stack contractions constantly in PopEar's clips, no textbook chart in sight, which is exactly the compression your ear needs a reference point for.

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A stacked contraction only sounds like a mystery word the first several times it goes by. Break a handful apart deliberately, on purpose, and the pattern starts announcing itself well before you consciously notice you've learned it.