I have files with both upper and lower case jpg/JPG extensions to the filesname. Both work for me. If you go to the Settings page on the LMS web page for your server, select the Advanced tab and then Logging in the main dropdown a the top you can then select a "Log Set.." of "Media Scanner". Then Apply it (bottom right). Then do a full rescan and you should see debug messages in the service log file in /var/svc/log/application-lmsd\:default.log (unless you've set the logging output to go someplace else). Best to do this with a small library or you will get a lot of output. The info may give some clues as to what it's doing different for files that work or not.
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