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Upgrading from 98SE to 2000 Pro

I am planning to upgrade my clients' pcs' from 98SE to 2000 Pro. What steps can I take to assure as smooth upgrade process? Is there any 'gotchas' that I should be looking for?

I did a couple, of which only 1 did, what I believe, a smooth transistion. One thing that I noticed was on the first upgrade, I followed someone steps and did not download the pack, whereas the second one I did. I also chose to convert to NTFS on the second system, whereas on the first system, I kept the FAT32 option.

Finally, I stopped the and removed items that were picked on the Upgrade report on the second system, whereas I chose just to proceed with the upgrade.

Also, the first system had an abundant more applications installed than the second system.

Does following the steps from the second upgrade make the difference when doing the upgrade?

Also, some applications did not show up on the Upgrade report as far as having incompatabilities, but I did have to reinstall the application just to correct any issue that I had. How can I avoid this, or better yet, how can I be sure that all the applications installed on a system functions correctly, without having run each and every application?

3 Solutions
mperez1216Author Commented:
Additional Comment:

Please include comments as far as what were your experiences were and your resolutions on problems. Also, are there any steps that I should take prior to commencing the upgrade.
Lee W, MVPTechnology and Business Process AdvisorCommented:
Personally, I don't think upgrading from 98 to 2000 (or XP) is a good idea.  I've seen many attempted upgrades fail, some minorly, some miserably.  I would strongly advise backing up (at best create ghost/drive image images of the 98 installs) and then do a fresh install.  It will clean up tons of crap likely in the registry and you can be sure that if you do have any problems in the future, they are not upgrade related.  (Keep in mind, 95, 98, Me are all of the same family of OS - which is significantly different from the other Microsoft OS family of NT/2000/XP/2003).
From my experience, do not do upgrades from 98 to anything.

I would do a fresh install.

I upgraded ~60 machines on my domain from 98 to 2000.  I did fresh installs.  There were a dozen or so done by person that worked here before me that were upgrades, and there were all kinds of flaky network problems and such.  Not so much programs and stuff the user would see.  But stuff I noticed when trying to administer the machines.  I'm trying to recall what these were, but it has been over 2 years ago.  I will try and remember.

I would definately recommend doing a fresh install, upgrading from 98 to 2000 is a very bumpy path at best.  You will be setting the stage for many issues and problems down the road.  The very best thing is to do fresh installs.  It may be a little more work up front but it will pay off for you and your users in the end.
mperez1216Author Commented:
Thank you for your thoughts. I split the points as to not to offend. Since I am only upgrading less than 20 out of 100, I think that I can manage. So far, I've upgraded 4 and replaced (with new installs) 3. I had to uninstall a couple of apps and reinstall them afterwards (including the av) and make a couple of software changes, but very minor stuff. Only significant problem that I came across was that a client was able to access a Windows 2000 share with no problem before the upgrade, but was unable to after the upgrade. I resolved this by adding the client as a user on the shared pc. Don't know if this is the right approach, but it works. Thoughts?

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