Just installed a SBS 2008 server and have a old DOS app (clipper) that reside on it. Xp boxes have no issue connect to servers share to run the app but HOW do I get a couple of old win 98 boes to connect to share and run app?
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Windows 98 bah get these older systems upgraded to something near the current time or leave them isolated off the domain for legacy reasons but don't spend days messing around with it.

You technically should be able to do it but I've never tried and wouldn't support those old OS for less than double my current rate.

How to enable Windows 98/ME/NT clients to logon to Windows 2003 based Domains

Client computers may not work correctly when you add a Windows Server 2008-based domain controller to an existing pre-Windows Server 2008 domain

This appears to be a SMB 2.0 issue with SBS 2008 that it supports by default that version of SMB. This occurs when using a network share on SBS 2008.
Without going into a lot of techincal details and having to disable the current version of SMB and who knows what other problems this would create, I would highly recommend upgrading the 98 machines to at least XP.
I know this is probably not what you want to hear, but it beats banging your head against the wall:-).
Thanks for the blast from the past of dos(clipper) haven't seen that one in a while.
Here is an excerpt from a post I found on how to solve this issue on Server 2008, in no way do I endorse this or would I recommend it on a SBS 2008 server, this is just for reference on what you are up against.
The specific issue was copying files on a network share and I think this would apply with a dos program on 98.

i solved it with following configuration.

On Windows 98 Client:

Install IE6 SP1 on Win98.

Install DSClient on Win98.
On Windows Server 2008:

SET SMB2 to "0"

SET EnableRaw to "0"

Check local Policy or if configured Domain Policy:
Microsoft network client: Digitally sign communications (if server agrees) to "enabled"
Microsoft network client: Digitally sign communications (always) to "disabled"
Microsoft network server: Digitally sign communications (if server agrees) to "enabled"
Microsoft network server: Digitally sign communications (always) to "disabled"

Check the LMcompatibilitylevel on the Windows Server 2008. I set it to "2" --> only NTLM Response and everything is fine.
 Here is the full link, 
You other option would be setup a terminal server and have the 98 machines connect to the app that way.

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