Here's the current status on this:

udisks sanely mounts vfat filesystems by using the "showexec" parameter
which only makes .exe, .com and .bat files gain the execute bit.
Unfortunately, this mount option isn't available for iso9660
filesystems. Adding the execute bit by default for all files in the
iso9660 filesystems will result in nautilus querying the user what to do
with files, which is something we want to avoid.

Someone needs to implement an equivalent "showexec" mount option for
iso9660 filesystems, at which point udisks can be changed to use it by
default.

-- 
Windows executable on unwritable removable media cannot execute with Wine due 
to lack of executable bit
https://bugs.launchpad.net/bugs/561479
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