The Italian language doesn't have many homophones words. When they do sound similar, they're usually pronounced with different accents (e|è (and/is) > ˈe/ˈɛ, or pésca|pèsca (to fish/peach) > ˈpeska/ˈpɛska.

In specific cases, we have words like a|ha (preposition 'to'/verb 'has') or da|dà|da' (preposition 'from'/verb 'gives'/imperative 'give') and a bunch of other similar prepositions that are pronounced exactly the same. You can only guess the right spelling by the context.

While dictating, though, I realized that sometimes several words next to each other could sound like another single word. In this case, we can only guess judging by the context, but apparently this speech-to-text technology is unable to do so.

Here's the examples I've found: