Files/Folders get weird names and become inaccessible on Samba share

It's a file name mangling problem. Samba is converting filenames down to old style DOS 8.3 filenames.

Edit /etc/smb.conf (*) and add mangled names=no to the [global] section and restart the smb service.

Reference: http://oreilly.com/openbook/samba/book/ch05_04.html

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(*) if the file is not there, type locate smb.conf to find it. Type sudo updatedb if locate does not find it and try again.

Came across this while looking for visibly the same issue but unrelated to Samba or any other specific file sharing utility.

(It took me a bit of google work to find this page which is why I'm adding my new answer for anyone else who finds this like I did)

The problem was only affecting a single user's directories (when viewed by others) and every mangled directory name was in the format of six(6) uppercase characters or numbers, one(1) ~ (tilde), followed by a single uppercase character or number.

Examples:

G2X4IA~5
O2T3KH~K
SYJ2IT~R

Solution:

The MAC user(s) in question should stop using trailing spaces and/or special characters in directory names. That's it. Almost every one of the directories in question had a trailing space, and the rest had a trailing special character (one actually had both which was a good test case). Simply removing them immediately cleared things up.