After a recent private tutoring session with a student, I confirmed just how difficult pronouncing contractions of will (‘ll) and will not (won’t) can be for English language learners (ELLs), and more specifically perhaps for Korean learners of English.
I thought about giving a quick resource here for pronouncing the pronoun + will contractions. This is by no way an official guide to pronunciation, but can prove helpful for those who are having some troubles as my student was. If you’re looking for a quick go to pronunciation reference that includes an auditory sample, check out Dictionary.com.
Contractions of Will with Pronunciation Key:
I + will —> I’ll [ahyl]
She + will —> She’ll [sheel; unstressed shil]
He + will —> He’ll [heel/heal; unstressed eel, hil]
We + will —> We’ll [weel; unstressed wil]
They + will —> They’ll [theyl]
It + will —> It’ll [ittle]
Jennifer + will —> Jennifer’ll [-ul]
Contractions of Will Not with Pronunciation Key:
I + will not —> I won’t [wohnt, wuhnt]
She + will not —> She won’t
He + will not —> He won’t
We + will not —> We won’t
They + will not —> They won’t
It + will not —> I won’t
SungBae + will not —> SungBae won’t
Using Contractions in Conversation: I also like to remind all of my students that when speaking in conversation, using contractions makes for more natural English. For example, “I’ll see you later” rather than “I will see you later.” Conversely, you shouldn’t use contractions when writing English unless you’re writing an informal communication to a close friend.
Jennifer Teacher 
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