SMB shares work with a negotiation between the capabilities of the server and 
the capabilities of the client.
By default, it tries to enable as many features as possible. By default (case 
sensitive=auto, preserve case=yes), when using Linux clients to connect to 
Linux servers, you'll get full case support. If you want to emulate the limited 
capabilities of a Windows server, you should at least set the following:

case sensitive=no
preserve case=no

That should give you the intended (mis)behavior.

How a file is represented on the filesystem differs from how a file is
resolved on the filesystem. Recent windows all have case-sensitive file
names, but it resolves case-insensitively. "preserve case" is about how
Samba creates files in shares (representation) while "case insensitive"
is about how Samba resolves them. "case sensitive=no" doesn't make all
Samba magically case insensitive, as you seem to think it should do.
There are a few other options that affect cases sensitivity, as you'll
see by reading up man smb.conf (or
http://oreilly.com/catalog/samba/chapter/book/ch05_04.html)

Does setting "preserve case=no" solve your issues ?

** Changed in: samba (Ubuntu)
   Importance: Undecided => Low

** Changed in: samba (Ubuntu)
       Status: New => Incomplete

-- 
case sensitivity option (case sensitive=no) is not honored
https://bugs.launchpad.net/bugs/561281
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