SMB Sharing with legacy Windows application

I have recently upgraded a client's Xserve to 10.5.x (just applied 10.5.3) from 10.4.11. The environment is Windows & Mac with approximately 70 users.
Without going into all of the problems I had with this upgrade, which ultimately became a re-format/clean install from scratch, I have one outstanding issue I have no clue with.
The Engineers in this company use a legacy windows app which is required for its specific functions. The Shares on the Leopard Server are mapped as drive letters and the workstation running the app have full access and using Windows Explorer can see all the file in the share, but the legacy app cannot.
So for example the E:/sharename/userdata/job/ contains many files. Using Windows Explorer all of these files are visible and have the correct perms, but when opening the app and using its Open Dialogue Window to point to the directory, all of the many folders within the share are visible and we can navigate within them, but the app does not see any files. It gives us 3 choices when viewing the files, *.dat, *.txt and ., but none of these show any of the files.
We also have a Windows 2003 Server which is the primary domain controller and runs Exchange 2003. If we copy the directories in question to a share on it or locally to the C: drive, then the app sees all of the files and can function normally.
Other current apps like Auto Cad and Microsoft Word and Excel function normally.
Any thoughts would be appreciated and I will provide any further information regarding the SMB setup if required.
This by-the-way worked fine when the server was running 10.4.11
I hope someone can shed some light on this.

Is the legacey application's development under your control or is a canned app?
How legacey? are we talking Windows 1.0, 286, 386, WorkGroups, 95, 98, Me, NT 3.0, NT-4, NT-2000, XP?
Do you have your heart set on Screen-scraping? or would you like to throw it out for other suggestions? (maybe screen-scraping is the only answer)
Any way, would you care to elaborate a little more on what you're doing? (yes, I am one of the more curious sorts).
Java Robot in 1.3 and later will do a limited amount of what you want, but you'll definetely need something else for full screen scraping.

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