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Need advice on doing upgrade from 2003 to server 2008 details in question

Posted on 2008-10-27
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Ok, if you need any more info of course just ask. We are currently running three servers,

1. file server (MS 2003)

2. exchange server (ms 2000 server and exchange 2003)

3. Print and intranet server (windows 2000 server)

We would like to install server 2008 on the file server. There are a number of issues. The current file server is 2003 enterprise. We only have purchased 2008 standard, so we can NOT do an in place upgrade, but from what I gather that is probably not the best move anyway.

So my question really boils down to what is the best set of steps one should take when doing a full bare metal install of 2008 server, when that server is currently running DHCP, DNS, hosting ALL the user accounts, accounting records..etc..etc..

I have a total back up of the drive. I have no problem with just blowing away everything there and then recreating it as needed. But I am sure there must be some sort of issues to be aware of that will cause me intense pain. :-)

The other two machines are both stand alone servers... so I am a little confused on how when installing the new server where will all the AD info be picked up from? I obviously can't have to recreate all the user accounts again... so how does one do that?

Setting up the dhcp scope and dns settings are pretty straight forward unless someone tells me otherwise...

I have looked all over the net and I have found reams and reams of info on this subject but quite honestly a lot of it contradicts other stuff, so I am not really clear on the best steps to take, both in doing the upgrade and preparing to do the upgrade so it's easier on the other side...

I am ready to learn... anyone have any suggestions on a worthwhile plan of action??

thanks in advance.

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Question by:LimestoneData
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Darius Ghassem earned 500 total points
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The link below will show you the actual steps to upgrade. Is the current file server you domain controller?

http://www.experts-exchange.com/OS/Microsoft_Operating_Systems/Server/Windows_Server_2008/Q_23665224.html
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by:LimestoneData
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yes the current file server is the DC

I am curious why I can't do an in place upgrade.. I mean I literally can't I get an error msg every time I try and not the standard uninstall FPE, it basically says the upgrade file is missing which is odd as the disk is actually from MS...
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by:Darius Ghassem
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If you have a 2003 Enterprise Server you can't upgrade to a 2008 Standard server. You must upgrade to a 2008 Enterprise server. Also, you must do adprep on the domain to configure the schema for AD.
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by:LimestoneData
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Sorry my bad, the server in place IS an enterprise and we did TRY to upgrade to 2008 enterprise that is where we got the error...

all adpreps were run all ready....

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by:LimestoneData
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I don't have the error in front of me as I am not at that location today... yes we have 2003 R2, Service Pack 2

It was (the error) something to the effect that upgrade file was missing, I will see if I can get someone to put the DVD in the drive and I'll fire it up via VNC and post the error.

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by:LimestoneData
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here is a screen cap of the install where it stalls... it just shows the upgrade option grayed out. I have attempted to install the right versions, enterprise to enterprise, I do have sp2 installed on the box and of course I have done all the prep that needs to be done to the AD I just don't get why this will not offer me an upgrade option and this is an ISO that MS suggested I download... right from their site... baffling...
upgrade-error.JPG
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by:Darius Ghassem
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So, you try to install Enterprise to Enterprise but you get this screen still? There was issue that I found with Vista but the solution was to reformat. Let's recap really quick.

You are trying to upgrade an 2003 Enterprise R2 32-bit with a 2008 Enterprise edition 32-bit, right?

I think this might be an OEM to full verison or vice versa issue.

Do you have another machine to install 2008 on? You can then allow replication to take place. Do you have more then one DC?
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by:LimestoneData
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Yes, enterprise to enterprise.

Both copies are full retail, which MS told me would provide an upgrade path.

Yes both are 32 bit.

I do not have another server to install 2008 to as the 2003 box is our main Dc and houses AD, DNS and DHCP...

So as this seems to be a dead issue I am more than willing to do a fresh install of 2008, but am really unsure about how to make sure AD will do what it needs to do on the new machine. As in the other two stand alone servers in the domain have copies of AD replicated to them.. but could I just do a bare metal install of 2008, then promote it and allow it be DC?

Does that mean I have to demote the current 2003 first and promote one of the 2000 boxes? But can that be done now that I have run all adprep stuff on all the machines?

Oh lord I"m more confused by the minute..

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by:Darius Ghassem
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If  your domain is 2003 forest level then you can't promote a 2000 machine to be a DC. Even if you have PC that has the requirements to load 2008 you can install 2008 on this machine then allow AD to replicate to it. Then once everything is good to go with AD you can move FSMO roles over to the temporary machine the demote the 2003 server format then install 2003 on the server then promote then transfer roles over to the new 2008 server. This will allow to fully remove 2003 then install.
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by:Darius Ghassem
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Sorry meant to say "then install 2008"

demote the 2003 server format "then install 2003" on the server
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by:LimestoneData
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Just so I can be clear I understand what you are saying....

"If  your domain is 2003 forest level then you can't promote a 2000 machine to be a DC. Even if you have PC that has the requirements to load 2008"

Yes it is 2003 forest level and both the secondary servers would be able to handle 2008 they are fairly new IBM boxes... but I see your point..

" you can install 2008 on this machine then allow AD to replicate to it. Then once everything is good to go with AD you can move FSMO roles over to the temporary machine the demote the 2003 server"

Hmmmm ok but then I would have two machines running 2008, right? This one on a temp basis, then the one you suggest to format below.

"format then install 2008 on the server then promote then transfer roles over to the new 2008 server. This will allow to fully remove 2003 then install."

But we only have ONE copy of 2008 to install...once I did the upgrade on the "temp" box to 2008, so I can format the 2003 to do a fresh install of 2008 I would need to remove the 2008 install as we don't have licenses for two installs... assuming I am understanding what you mean...

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by:Darius Ghassem
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Yes, that is correct but you will have time to use the 2008 license twice if you are just going to remove the temp 2008 server once you get the 2003 server rebuilt. You can make a 2000 verison of MS to be a DC if your forest level is 2003 you must install another 2003 server or 2008.

Even if you want to make the temp DC 2003 server that is fine but you need to create a temp DC so you can replicate AD over and have your network working while you rebuild the other server.
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by:LimestoneData
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Hmmmm ok now you have me thinking.... so then I could install 2003 on one of the 2000 boxes... use it as the temp DC, wait for everything to replicate... then once that is done and I do the fresh install of 2008 I don't need to remove the 2003 install as it is a full copy as well. I would just need to demote the temp DC (2003) and promote the 2008 install? Am I finally getting this hahaha
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by:Darius Ghassem
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You are right on. This will allow you migrate easier without downtime. You never know if you will have problems so having a server running while to build another gives you ability to be at ease knowing you have a DC running.
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Ok so how about this.. haha.. it never ends. We install 2003 on our current print server, which is a stand alone server running W2K SP4, we promote it to DC. Everyone is able to log into it, and they can still access their mail as the OTHER W2K box is the Exchange server.. all good so far.

We then take the orginal 2003 DC, wipe it clean do a bare metal install of 2008. BUT, they are now telling me they would like to install SBS 2008, my understanding is that is NOT a full fledged version of Server 2008 but is based on the same technologies... but the reasons they want it are the fact that Exchange 2007 is included... and sharepoint services are also included both things they would like and the price difference is very minimal...

So  my amended sorta related question is, how much of a monster would it be to install SBS 2008 make that the main DC etc..etc.. then migrate exchange from the current location into the new 2007 location? Plus I am always told having your DC, file server etc on the same box as exchange is not a wise thing, but SBS comes with it integrated...

Any thoughts, ya or nay?


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by:Darius Ghassem
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SBS is another beast. I haven't migrated from a 2003 domain into an SBS domain. SBS has it's quarks but if setup correctly it can be a good resource.
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by:LimestoneData
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Ok latest update.... my goodness..

What we know...

For whatever reason the Server 2008 discs will NOT allow an upgrade of our 2003 R2 installation.

My thought based on the advice given in this question was to upgrade one of my TWO remaining W2K servers, and promote it to a DC, then take our current DC (2003 R2) off line after demoting it. The doing a bare metal install of either 2008 server or SBS 2008.

FYI, I can't do an upgrade of 2003 R2 to SBS 2008 as SBS is ONLY x64 and of course the 2003 R1 is x32

So I popped in our discs to upgrade one of the W2K boxes and it too says we can NOT do an upgrade... WTF? I have no clue what is going on here...

So my next question to get this ungodly upgrade done is this,

Can I simply PROMOTE one of the W2K boxes back to DC status, then demote the 2003 R1 box?

Once everything is replicated and working, take the 2003 R1 offline and do the bare metal upgrade to whatever flavor 2008?

Is there an issue with that idea??

Thanks in advance
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by:Darius Ghassem
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Is your domain is 2003 forest level, right? So, since you have it at this level you can't install a 2000 domain controller.
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by:LimestoneData
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Yes it is... so basically I am screwed hahaha... I need to upgrade at least the DC box right now running 2003 R2 so does this mean I need a FOURTH server to put into the domain for the time being, in other words to make it a 2003 DC, then I can take the current one off line and do the bare metal install?

Boy this just gets more and more involved... and annoying...

So my current opinion of what needs to be done is....

Do fresh install of a NEW box with 2003 R2 on it. Add it to the network promote it and more all services to it. DHCP, DNS, etc, etc.. all the stuff the current one is running.

Once finished propagating (how long should that take?) demote the original 2003 box.

Format and do a clean full install of SBS or whatever flavor of 2008.

Once that is done, promote it and move all the services back from the temp box.

Once that has propagated, I can demote and remove my temp server from the domain leaving the original three boxes..

Am I missing anything or doing anything more than I need to do??


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by:Darius Ghassem
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No, everything seems in order. That is what you need to do.

I would wait at least a day to make sure all information has replicated and network services are running correctly. A way to test is to shutdown the server you will be formatting. Make sure you move over the FSMO roles. Make the new DC a GC.
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by:LimestoneData
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Make sure you move over the FSMO roles. Make the new DC a GC.

Meaning, once the new server is up and running as a DC the two items above have to be moved back?


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by:Darius Ghassem
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Yes & when you bring up the temp DC make sure you move these roles over before formatting the server you are going to install 2008 on.
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by:LimestoneData
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yeah makes good sense.. thanks... ok well time to install my temp server yikes...
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Good luck!
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by:LimestoneData
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Ok so far no major issues.

I have installed the tempserver, it has DNS, DHCP and GC running. I have not moved over the roles yet as I wanted to read up a little more on that and it was getting late tonight and didn't want to muck about too much.

So early Thursday morning (it's late Tuesday night here now) I will shut down the current server I want to format.. and as long as everyone can keep logging in, seeing their files (being moved to the temp box in the morning) and so forth I can assume all is well enough to install the new box?

Anything obvious you can think of I might be missing?

Once I have the NEW server up and in place I should wait a day or so for it fully propagate as well before I take down the temp server, correct?


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by:LimestoneData
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Well ya knew it couldn't be totally smooth sailing...

So  I started moving over the FSMO tonight.. and all went well except ONE

When I try to move the Infrastructure role it tells me the new server is a GC and that role should NOT be moved to a GC server...

Thoughts?


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by:Darius Ghassem
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That is fine just move the infrastructure master role over. Don't worry about that.
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by:LimestoneData
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Sweet thanks, consider it done... I assumed it would be ok, but you know when MS pops up those DO NOT do it windows I like to double check


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Ok this might be a dumb question (like all my others haha) but do I have to demote the original server using dcpromo before I take it off line to do the fresh install?

I actually turned it off today and everybody logged in with no issues... for about four hours.. but before I do the reinstall just curious if it makes any difference or should I log back in and demote it??

Thanks,
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by:Darius Ghassem
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Yes, you need to demote the server before doing a fresh install. You always want to demote a DC if you can.
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Well I think we are at the end of the line here. I actually formated and did a bare metal of install of my NEW server after almost 48 hours of the temp server up and handling all the logins and all network services. The last 12 with the original DC turned off.

I demoted the 2003 DC, did the install and it is now up and running in the domain as a DC, I have both running right now the new one and the temp one.. all is going very well.. which means I know I am headed for some trouble soon nothing can be this smooth

So  I am going to give it one more day to make sure everything is cool on the new box, then demote and remove the temp box.

Was wondering if you might have good resources to point me to for login scripts.. I would really like if possible to have all their drives mapped at logon... and we have a print tracking module that loads via that same script...

So assuming nothing nasty comes up overnight or in the next day I will close this question off on the weekend and award the points to my trusty tech partner darius... thanks dude, much appreciated... worth the 20 bucks this month for sure haha


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This is a pretty cool website that I have used before. I'm glad everything is working. I know it has been a long post but I'm glad we got a solution that fits your situation.

http://www.computerperformance.co.uk/Logon/logon_scripts.htm

http://msmvps.com/blogs/kwsupport/archive/2004/11/03/17830.aspx
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by:LimestoneData
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Oddly enough I found BOTH of those sites last night as I was poking around the net and trusty google... I also found the script below which to me looks perfect but I have questions about how to change it for me.. and of course I need my script to do one more thing which I'm not sure how to add... any thoughts?

I am curious what I have to change to make it work on MY server.I note they have winnt as the a default location mine is not... plus do I need to add multiple instances of the line Select Case GroupObject.Name with the .Name part being one of my Group names? Also curious as I have people that are members of more than one group do they have to have the group in the script as their Default Group? Plus the most important thing of all do I just call this vbs script from a bat file some how?

We also have this line in our login script that must run for each user...

cmd /c "start \\printsrv\pccclient\win\pc-client-local-cache.exe -- silent"

So do I run the script with the above line in, then the next line calls the vbs script somehow??

I realize this is off topic to some degree but not really as it's all related to doing this upgrade...

Any help or direction pointing would be much appreciated. Thanks




' VBScript to map drives based on group membership
'---------------------------------------------------
On Error Resume Next
 
Set WshNetwork = CreateObject("WScript.Network")
 
DomainString = WshNetwork.UserDomain
UserString = WshNetwork.UserName
 
Set UserObj = GetObject("WinNT://" & DomainString & "/" & UserString)
 
'unmap all drives
WshNetwork.RemoveNetworkDrive "V:",true,true
WshNetwork.RemoveNetworkDrive "W:",true,true
WshNetwork.RemoveNetworkDrive "X:",true,true
 
 
For Each GroupObject In UserObj.Groups
        Select Case GroupObject.Name
                Case "Group 1"
                        WshNetwork.MapNetworkDrive "Z:", "\\<Server>\<Share>"
                        wshNetwork.AddWindowsPrinterConnection "\\<Server>\<Share>"
                Case "Group 2"
                        WshNetwork.MapNetworkDrive "Y:", "\\<Server>\<Share>"
                Case "Group 3"
                        WshNetwork.MapNetworkDrive "X:", "\\<Server>\<Share>"
        End Select
Next
 
WScript.Quit
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by:LimestoneData
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A long haul due to my inexperience but your patience was much appreciated and all seems to be humming along perfectly now a few days after the upgrade was completed
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