Oh goodness. Where to start? Yes. Windows will search in the metadata in fields it recognizes. Yes, Windows sees the metadata from Lightroom if it has been saved to the photo. I believe this is an automatic thing now for it to write with CC. If not, go to Catalog Settings → Metadata → and make sure that automatically write changes into XMP is checked. When that's checked, and LR writes the metadata this is the result: Anything in "tags" is the keywords that I write to photos. You can see Matthew, Our Family, etc. (I removed last names for privacy.) Anything in the Title is where I have written in the "Caption" field in Lightroom. I believe it will also show up in "Subject" in Windows too.