I ran into an issue where cetain images served from a virtual directory, mapped to Network Attached Storage (NAS) via a UNC path would not display.  After quite a bit of detective work I noticed that the images failing to display where those of about 600KB in size.  If I resized the images under 200KB they dispalyed fine.  I found some information on MSDN that states that IIS caches the remote files for faster delivery.  Periodically, IIS poles the remote locations (UNC Paths) for file changes.  I believe the following registry entry to be the cause:

MaxCachedFileSize

Registry Path: HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Services\InetInfo\Parameters

Data Type: REG_DWORD

Default Value: 256 KB (262,144 bytes)

Controls the maximum size of cache files. The default is 256 KB if no value is present.