It is possible to show all records in your table and then use Import Records | Folder to import all the images in a selected folder. You can select the "import matching" option and specify that the filenames be the matching field.
And would the program be able to recognize that the image was going into the right file? With some of the folders, there are more images than there are files.
You'll have to explain that in more detail. What do you mean by "file"? do you mean "record" in the database table or something else?