Muddle basil leaves in olive oil and let sit for at least two hours.
Using a sieve, remove the basil leaves. (You've just made basil-infused olive oil. It's so good and so easy that you will want to make it all of the time.)
In the bowl of a stand mixer with paddle, combine the flour, milk, yeast, salt, and eggs. Mix at low speed until incorporated. The dough will be stiff at this point.
Replace the mixer paddle with a dough hook. At medium speed, gradually add the sugar in 5 or 6 increments, mixing for about two minutes between each addition.
Continue mixing at medium speed until the dough starts to come together around the hook.
Change back to the mixer paddle. Add 1/2 cup of the basil-infused olive oil and mix at low speed until it is incorporated. This will take a while.
Transfer the dough to a lightly oiled container. Cover and let sit for 2 hours in a warm location.
Roll the dough out to a 1/4" thick oval.
Spread the jelly on the dough, leaving about a 1/2" empty on all sides.
Starting with the long side of the oval, roll the dough over the jam to form a log.
Cut the log into 12 even pieces.
Shove the pieces into the cupcake wrappers however you want. Notice from the photo at the top of this post that I did this lots of different ways. They all look different and they all look pretty.
Cover the cupcake tin and let rise in a warm place for another two hours.
Bake at 400 F for 20 minutes.
If desired, drizzle with olive oil and spread watermelon jelly on top.