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We have been trying to connect Win98 clients to Server 2008 without any luck. We've installed DSClient (client), setup NTLMv2 seemingly correctly (client/server), enabled WINS (client/server), disabled forced signing of communications (server), and still receive an Invalid Password error.

What's strange is that the Security event log shows the client logging in, obtaining user/group permissions, then immediately logging out. There are no errors on the server side. I inspected the packets (wireshark), and it appeared that the Win98 box was receiving the success notification, but then still showing the error.

Any insight on how to address this? Is there a way to debug the session from the Win98 side?

FYI: We currently cannot upgrade to XP/Vista/Win7 until our current DOS-based order processing system is replaced. At the same time, our company is growing so we need to upgrade beyond our old NT 4 servers currently used for file storage.

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Wow, Windows 98 to Windows Server 2008. Seems more that ten years, like 30 years... ;-) – splattne Jul 14 '09 at 6:52
up vote 1 down vote accepted

I haven't tried this yet, but perhaps I will (since I still have one Customer using Windows 98SE-based machines). Getting Windows 98 to play well with Windows Server 2003 took some doing. Getting logons to work was fairly straightforward, but there are some "creeping" issues in various versions of the DSClient code that pop up when you bring account lockout into the mix.

If you don't have the 323466 hotfix for DSClient then get it-- you want it. You'll want a VREDIR.VXD dated 8/6/2002 or later. That may be enough to solve your problem, but not having tried it myself I can't say. (That hotfix is no longer publicly available, but I might know where you can find a copy. You can read an archived version of the article text here:

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I couldn't find this hotfix anywhere ... let me know if you think of where a copy is available. – Beep beep Jul 14 '09 at 19:12

Could you virtualise a 98 box inside your system to do this. If required you could even virtualise a 98/ nt 4 DS for this app until it could be upgraded?

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For security reasons, we have the 98 sessions virtualized within XP. However, we need the virtual 98 sessions to access a network share on Server 2008 (actually, 10 shared drives) ... unless there's some type of backdoor option to map the drives on XP then leverage those drives in the 98 VMWare session. – Beep beep Jul 14 '09 at 6:56
Could you deploy a virtual linux box which can access the box, and then share them down using samba directly to the 98 boxes, but the whole thing is only accessible inside the VM network keeping it secure via encapsulation? – Spence Jul 14 '09 at 7:01
@Spence - can Samba re-share a drive like that? Do you know how I would find out more? – Beep beep Jul 14 '09 at 7:08
pretty much any modern linux would have access to the samba package, most times preinstalled. It should be much more tolerant of older connections than the server 2k8 box is. – Spence Jul 14 '09 at 9:33
@Spence - we use Samba currently, but the data resides on the Samba box (authenticating users on Win NT). I'm not sure how it would be leveraged as a go-between from the 2k8 Server to 98 ... are you suggesting there's some way to store data on 2k8, but have Samba share that to the Win98 sessions? – Beep beep Jul 14 '09 at 19:54

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