Bring a pot of water to a boil. Add a generous pinch of sea salt to the boiling water. Add pasta and cook according to package directions until al dente, then drain water and place the pasta in a large mixing bowl and let cool.
While the pasta is cooking, dice the pepperoni (or chicken), olives, and cucumber and add to the pasta in the mixing bowl.
Add ¾ bottle of Italian dressing and thoroughly mix all the ingredients together. Add salt and pepper. Cover and place in the refrigerator for 2-3 hours and then add the remaining ¼ bottle of the Italian dressing and mix thoroughly. Taste for seasoning and add more salt and pepper, if needed.