Most of the time it's because the file has nothing to search. Silhouette files you import or design yourself arrive in your library with no category, no description, and often just a filename. Since search looks through those details, an untagged file is basically invisible. Adding keywords to your Silhouette Studio files fixes it. This free guide shows you exactly which keywords to use.
The fastest way is custom keywords. Silhouette Studio's built-in categories don't cover sublimation, stickers, DTF, or UV, so keywords are the only way to group your Silhouette library the way you actually think about it. Tag each design from several angles, occasion, subject, product type, and technique, and it will turn up no matter how you search. The starter guide gives you a copy-from keyword list to make it quick.
Select the file, open the Show Properties panel, and you'll find fields for the name, description, category, and keywords. Type your keywords into the keyword field and they become searchable, even if that word appears nowhere else in the file. You set them one file at a time, so the trick is to tag as you go rather than fixing your whole Silhouette Studio library at once.