Flare your lips and lift the mid-front tongue close to the roof of your mouth. Blow air through without voicing.

Americans pronounce shouldn't as SHUU-duhnt (/ˈʃʊdənt/). In "shouldn't", the "t" between vowels sounds like a quick "d" — the tongue briefly taps the ridge behind the upper teeth. This is called the Flap T, and it's why Americans sound more relaxed than the textbook. So instead of SHUU·tuhnt, you get SHUU·duhnt. Stress falls on the first syllable — keep everything else short and quick. You'll hear it in sentences like "You shouldn't have waited so long" or "She shouldn't have sent that email" — more examples below.
Record yourself saying "shouldn't" and play it back. The mic stays on your device — nothing's uploaded.
2 syllables, 6 sounds. Tap a syllable to jump to its row, then explore each sound's mouth shape and how it's made.
Quickly bounce the front of your tongue against the roof of your mouth. Same as Flap T — a quick tap without stopping airflow.

Relax your lips, jaw, and tongue completely. Drop your jaw slightly and keep the tongue neutral.
The schwa before N disappears — N becomes the vowel of the syllable. Go straight from the previous consonant to N.

Touch the tip or front edge of your tongue to the roof of your mouth just behind your teeth. Keep your jaw relaxed. Stop the air, then release with a puff.

Click any sentence to see the full breakdown — every link, every reduction, every flap-T.
The textbook way isn't wrong — it's just not how anyone actually says it.
In "shouldn't", the "t" between vowels sounds like a quick "d" — the tongue briefly taps the ridge behind the upper teeth. /t/ or /d/ becomes a quick tap [ɾ] — sounds like a soft D. The tongue briefly taps the ridge behind the upper teeth.
In "shouldn't", the short unstressed vowel before "n" disappears — the schwa is absorbed and the "n" becomes the syllable nucleus on its own. Schwa is absorbed — consonant becomes the syllable nucleus.
Stress falls on the first syllable, not the others. Stretch SHUU — keep everything else short and quick.
Don't pronounce the first syllable too fully. The unstressed syllable reduces to a schwa — the lazy "uh" sound — in casual speech.