Migrate Server 2003 to Server 2008

RJM62

RJM62

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Geek on the Hill
I've been out of the loop for a while, but despite being advised of that fact, an old client of mine wants me -- and me only -- to make an all-expenses-paid trip to their not-unpleasant neck of the woods to migrate their Windows 2003 SBS server to a new Windows 2008 server.

The server basically runs fileserver and DC duties. I believe the only third-party software running on it is Quickbooks.

My question is simply, based on the more recent experiences of people here, what's the best way to proceed?

My inclination is to configure the new box as extra DC, copy the data over, inatell and configure Quickbooks on the new server, demote the 2003 box, make sure everything works, and then retire the old machine and store it in a closet for a while -- just in case. However, like I said, I've been out of the loop for a while.

Any comments / advice appreciated.

-Rich
 
I'm no Windows guy, but your words match those of our Windows guys doing same thing.

Might consider making the new box a host VM server and building the new machine inside a VM. Nowadays that's not much of a hardware penalty and gives you some flexibility to move the VM image to other hardware if the machine craps out later. Also gives you a way to do an upgrade of a VM image later and roll back if it screws up.

All depends on if you feel comfortable helping them remotely get it online if the VM server itself were to lock out the VM for some reason. That's the biggest "risk" in doing it.

We like Xen for Windows virtuals and KVM for Linux, we kicked VMWare to the curb when their pricing tripled with no significant improvements in what we do, in a single year.
 
Not an expert by any means, but when we migrated from 2003 to 2008, that is pretty much what we did.

If the old hardware is still working, consider keeping it hooked up in a separate location on the same network as a failover for whatever critical functions the main box fulfills.
 
Thanks.

I really hadn't thought about virtualizing it... interesting idea. I'll look into that.

I'm fairly comfortable about doing the initial set-up onsite, mainly because they have an excellent resource in the form of a tech-savvy manager who knows enough to know when to stop and call for help. She can handle all of the day-to-day administration of the system, and 99 percent of the oddball things that pop up; and for the other 1 percent, I'm only a phone call away.

She actually could probably handle the migration on her own with a bit of coaching, truth be told; but she prefers that I come down and we do it together. That's how we've done migrations and other big jobs in the past.

I did think about keeping the old machine on as an extra controller (or even just a place to store a local data backup), weilke. I'm still undecided about it. I'd like to look at and touch the machine first, and also do some research about how well the two systems will get along. Like I said, I've been out of that end of the business for a while.

Thanks again,

-Rich
 
We're still in the process of migrating from XP desktops and Server 2003 to Win 7 desktops and SBS 2011. Ran the scripts and by and large it worked. BTW, we're running the Windows virtulization server on the hardware and SBS 2011, a Linux instance and a BSD Unix instance on top of it in one box with good results. We were able to reduce our electric bill by $50 a month by getting rid of three boxes.
 
I wonder if SBS 2011 is an option for them... She specified Server 2008, but I can't think of a reason offhand why SBS 2011 wouldn't work for then. Something else to look into. Thanks.

-Rich
 
Didn't expect to see a post like this on here. Missing one critical piece of this puzzle though.

You say they are on SBS2003. Are they using Exchange? If yes, I would strongly advise you to start fresh with a new domain (provided they don't have too many workstations to migrate). Obviously they would either want to get SBS2011 (if they want Sharepoint) or just go Server 08' R2 and standalone Exchange (my preferred option but I'm an Exchange guy).

If you're just moving DC and fileshare infrastructure it should be a lot easier. Upgrade the Active Directory on the old server, join the 2008, promote to DC, migrated roles, move data. Take a backup and then install Quickbooks. Demote the old one, check the clients for static IPs. I like to add the old server's IP to the new server and create a DNS record for it. I would definitely rename the old server and change its IP to make sure you migrate fully.

I've done a bunch of these so let me know if you want additional info.

Dan

Who'd have thought my first post on a pilots website would be IT info.
 
dtm6582 said:
Didn't expect to see a post like this on here. Missing one critical piece of this puzzle though.

You say they are on SBS2003. Are they using Exchange? If yes, I would strongly advise you to start fresh with a new domain (provided they don't have too many workstations to migrate). Obviously they would either want to get SBS2011 (if they want Sharepoint) or just go Server 08' R2 and standalone Exchange (my preferred option but I'm an Exchange guy).

If you're just moving DC and fileshare infrastructure it should be a lot easier. Upgrade the Active Directory on the old server, join the 2008, promote to DC, migrated roles, move data. Take a backup and then install Quickbooks. Demote the old one, check the clients for static IPs. I like to add the old server's IP to the new server and create a DNS record for it. I would definitely rename the old server and change its IP to make sure you migrate fully.

I've done a bunch of these so let me know if you want additional info.

Dan

Who'd have thought my first post on a pilots website would be IT info.
Click to expand...


Welcome! And of course, the fact that this is an internet pilot's group implies a certain level of computer awareness. Lots of geeks on this particular forum.
 
dtm6582 said:
Didn't expect to see a post like this on here. Missing one critical piece of this puzzle though.

You say they are on SBS2003. Are they using Exchange? If yes, I would strongly advise you to start fresh with a new domain (provided they don't have too many workstations to migrate). Obviously they would either want to get SBS2011 (if they want Sharepoint) or just go Server 08' R2 and standalone Exchange (my preferred option but I'm an Exchange guy).

If you're just moving DC and fileshare infrastructure it should be a lot easier. Upgrade the Active Directory on the old server, join the 2008, promote to DC, migrated roles, move data. Take a backup and then install Quickbooks. Demote the old one, check the clients for static IPs. I like to add the old server's IP to the new server and create a DNS record for it. I would definitely rename the old server and change its IP to make sure you migrate fully.

I've done a bunch of these so let me know if you want additional info.

Dan

Who'd have thought my first post on a pilots website would be IT info.
Click to expand...

Thanks Dan, and welcome.

When I set up the 2003 server years ago, they were not using Exchange. I have no reason to believe they are now. This outfit doesn't even have a Web site (nor even an Internet domain name), nor want one. They get all their work from other contractors and do not want an "Internet presence."

I know. I've tried to sell them on a Web site since... forever.

Thanks for your offer of help. I may take you up on it.

-Rich
 
RJM62 said:
Thanks Dan, and welcome.

When I set up the 2003 server years ago, they were not using Exchange. I have no reason to believe they are now. This outfit doesn't even have a Web site (nor even an Internet domain name), nor want one. They get all their work from other contractors and do not want an "Internet presence."

I know. I've tried to sell them on a Web site since... forever.

Thanks for your offer of help. I may take you up on it.

-Rich
Click to expand...

I have a few clients like this too. I even have one where they have 1 email address for the entire firm and everyone shares it...try telling them they can each have their own account..."oh, we don't want that".

Anyway, sounds like they just need something basic then. Obviously you have a lot of options but I would skip SBS if they aren't using Sharepoint or Exchange. Less installed software tends to equal fewer "surprises", especially since SBS will be more expensive to purchase and license than server standard.

I've been doing a lot of virtualization work using Hyper-V the last few years. This is what I would do:

Buy Server Standard 2008 R2. Install this on the physical machine. Then install Hyper-V and set up a virtual machine for their production server (2008 R2 standard includes 1 physical and 1 virtual license). I'll let you read up on Hyper-V but it adds so many benefits that I haven't set up a non-virtual server in over a year (I set up a lot of servers).

Sounds like you have the migration procedure down pretty well. Have you worked with Server 08 yet? There are a few gotcha's to be aware of, nothing earth shattering though. Backups can be frustrating.

Anyway, good luck. I do this for a living so I'm happy to answer questions if any come up.
 
RJM62 said:
I wonder if SBS 2011 is an option for them... She specified Server 2008, but I can't think of a reason offhand why SBS 2011 wouldn't work for then. Something else to look into. Thanks.

-Rich
Click to expand...

Also, just to clarify, SBS2011 is just Server 2008 R2 with Exchange and Sharepoint added. No benefit in using this if they aren't going for those features.
 
dtm6582 said:
I have a few clients like this too. I even have one where they have 1 email address for the entire firm and everyone shares it...try telling them they can each have their own account..."oh, we don't want that".
Click to expand...

Do they have a teletyper as well :)
 
dtm6582 said:
I have a few clients like this too. I even have one where they have 1 email address for the entire firm and everyone shares it...try telling them they can each have their own account..."oh, we don't want that".

Anyway, sounds like they just need something basic then. Obviously you have a lot of options but I would skip SBS if they aren't using Sharepoint or Exchange. Less installed software tends to equal fewer "surprises", especially since SBS will be more expensive to purchase and license than server standard.

I've been doing a lot of virtualization work using Hyper-V the last few years. This is what I would do:

Buy Server Standard 2008 R2. Install this on the physical machine. Then install Hyper-V and set up a virtual machine for their production server (2008 R2 standard includes 1 physical and 1 virtual license). I'll let you read up on Hyper-V but it adds so many benefits that I haven't set up a non-virtual server in over a year (I set up a lot of servers).

Sounds like you have the migration procedure down pretty well. Have you worked with Server 08 yet? There are a few gotcha's to be aware of, nothing earth shattering though. Backups can be frustrating.

Anyway, good luck. I do this for a living so I'm happy to answer questions if any come up.
Click to expand...

Thanks again.

I used to do it for a living, too, but I sold that business a while ago and just do Web design now, about half-time. The other half I fish, putter around in the garden, fly when I have the money, and generally goof off when I don't. Not a bad life, actually.

I haven't worked with Server 2008 at all. I was already phasing myself out of that end of the business by the time it came out. None of my existing clients needed it and I wasn't accepting new ones, so I never had the need or the opportunity.

dtm6582 said:
Also, just to clarify, SBS2011 is just Server 2008 R2 with Exchange and Sharepoint added. No benefit in using this if they aren't going for those features.
Click to expand...

Got it. Thanks again.

-Rich
 
dtm6582 said:
Also, just to clarify, SBS2011 is just Server 2008 R2 with Exchange and Sharepoint added. No benefit in using this if they aren't going for those features.
Click to expand...

SBS is now a dead product. You can't buy it anymore. Microsoft is convinced that everyone is moving to the cloud (Office 365). Windows Server 2012 is now the shipping version.
 
New SBS2011 machines can still be had. Whether MS likes the idea, I know not.

-Rich
 
RJM62 said:
New SBS2011 machines can still be had. Whether MS likes the idea, I know not.

-Rich
Click to expand...

My mistake. Essentials is still just RC and hasn't quite shipped, yet. When that happens (any day now), SBS won't be available anymore. Windows Server 2012 has already shipped, so 2008 R2 is no longer available for purchase, although you can install it with backwards licensing rights. There are are many advantages to virtualizing and I have done it in single server environments. One complication would be if you are backing up to a tape device, it complicates presenting that to the virtual server (SCSI pass through is supported on VMWare, but not HyperV). Also, if you have any key dongles, required by some proprietary software, you may need a separate device to present that to the virtual server. MS licensing has changed for virtual instances. Standard edition now includes two virtual instances and are "stackable". Enterprise edition is gone. Datacenter is still unlimited instances.
 
dtm6582 said:
Didn't expect to see a post like this on here. Missing one critical piece of this puzzle though.

You say they are on SBS2003. Are they using Exchange? If yes, I would strongly advise you to start fresh with a new domain (provided they don't have too many workstations to migrate). Obviously they would either want to get SBS2011 (if they want Sharepoint) or just go Server 08' R2 and standalone Exchange (my preferred option but I'm an Exchange guy).

If you're just moving DC and fileshare infrastructure it should be a lot easier. Upgrade the Active Directory on the old server, join the 2008, promote to DC, migrated roles, move data. Take a backup and then install Quickbooks. Demote the old one, check the clients for static IPs. I like to add the old server's IP to the new server and create a DNS record for it. I would definitely rename the old server and change its IP to make sure you migrate fully.

I've done a bunch of these so let me know if you want additional info.

Dan

Who'd have thought my first post on a pilots website would be IT info.
Click to expand...

Welcome to PoA. This great goup of guys will help with about any problem. We talk about flying a little bit here, too.
 
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