I have found that the image search tool does not always function the way that you would expect it to. I do not know what image names that you are trying to find, but I will give a few pointers from my experience.
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If I upload an image directly to a product page, that image does not show up in Settings->Files when I search for it.
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No matter how I upload an image, direct to a product page or via the Settings->Files->Upload files page, all spaces, and special characters (except _ underscores and - hyphens) are converted to _ underscores. For example “CAT#486-2 front silo.jpg” is converted to “CAT_486-2_front_silo.jpg”.
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If I upload a file that already exists, a random string of characters and numbers is appended before the file extension and after the original file name. I learned this the hard way after bulk uploading 3000 images 12 times. I am still removing all of the duplicates months later.
My workarounds:
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My first step when uploading images is to make sure that all spaces and excluded special characters are changed to _ underscores before the upload.
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I search for the image file name that I want to upload and delete all versions with the auto appended string of numbers and characters mentioned in #3 above.
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I now only upload the file through Settings->Files->Upload files first and then add the image to the product via Excelify, or CSV push, for non-critical updates, or manually with the “Add media from URL” dropdown on the product page for critical updates.
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When searching for files, I try to put in the exact file name that I am looking for first.
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I put in the words that I believe are in the file name separated by spaces listed from general to specific. It seems to find the image even if I just put any combination of words that are in the filename.
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I have noticed that the special characters are not used in the search tool at all, including the _ and - allowed in the file names.
Hope that this helped. It was and is a frustrating problem for new users like myself.