SBS 2003 Migration to Server 2008 Pros and Cons?

I do believe it is your guide which was awesome.  I've been questioned a bit by management as to why I have not migrated to the "newer" OS's.  

My thoughts have been that it's not broke, so don't fix it.  But I do feel there needs to be a transition at some point.  As I stated, we're not going to use exchange in here as it's hosted now.  I have a 550GB partition on the SBS now and on that is where you find the users folders and some accounting software.  

Wanting to put the 2008 version to use as well.  I want to get some experience with it.  So I thought about "fixing" it when it's not "broke".  

However keep in mind that the SBS is all junked up.  I need to run chkdisk on it for example and there's been things added to it, removed from it and such for years.  It really needs cleaned.  So I thought I'd just move on.

Your thoughts would be much appreciated.

-MAc

Forgot to say, I would still be using SBs2011 if you don't want exchange.  The benefits it brings far outways the cons.  You will probably find it's also cheaper than standard edition.

Then you are well placed if you decide to bring Exchange back in house.

Are you you using remote web workplace with SBS?  If you lose that with std product
You might consider looking at SBS Essentials 2011, currently out as release candidate ...up to 25 users should integrate with your hosted exchange and give you remote web Workplace

With other here, SBS-Essentials is a perfect fit if you can hold out for the release.

To answer the initial question though: migrate.

Unless you have a real need and compelling argument to install new, migrating is always the better choice. I can count on one hand the number of times I thought a new install was required in the 11 years that Active Directory has been out.

-Cliff

Wow,  a lot of good info.  The server I have that I want to use is an HP DL380 with a drive space of around 500gb.  The SBS was set up and configured when I came into this, so it is configured with a standard "C" drive and then a "DATA" drive "E".  On "E" is where my users folders and pretty much all "shares" are placed.  

How would you guys then approach this?  Obviously I would like for this to be an improvement over what is there but keep the basic config scheme overall so as to not upset things mroe than need.  I have activation for several versions of Server 08 and 03 but I don't think SBS is included in there.  Ideally I wouldn't spend any money given that I have 2008 already there.

What I'm hearing here is go with the SBS Essentials on the new HP DL380.  That way I have the option of bringing exchange back in house in the future.  I don't see that happening given the rather low cost of having it hosted by "RackSpace".  But the option would be there.

What about leaving the users shares on the current SBS but demoting it while promoting the other thus lessening the amount of data that needs to be moved, if any.

That way the nes SBS2011 Essentials would be where AD, DNS and all such as that would be handled and the old SBS would just be another file server on the network.

Please forgive the rather low level tech aspect of how I approach this.  Although I've been doing this about 4 years, I've only needed to do new installs, never a migration.  Given the SBS being the "heart" of the network, I've opted to leave it alone.

I would also like to rework the scheme overall.  This is set up is based on the 10.0.0.X scheme.  As in my DNS server (SBS) is 10.0.0.2)  default gateway is 10.0.0.223 and for some reason the guy that set it up has the domain listed as "mail" everywhere on the network when in fact is it retinanet.  I get that it works, but it just seems a bit sub optimal.

Suggestions?  

Just an FYI this is a small network.  A total of 46 nodes, 15 users, Cisco ASA 5505, the old SBS2003, 3 Server 2003 boxes, (one is used for Citrix) a Storage Server2003 box (10tb for housing image files) 90% of users on XP with a few 7's.  Two CC terminals and three networked printers.  Also an internal AP and one DMX interface that is for the wireless AP for guests. An HP Procurve 2900-48G and an HP 8 Slot autoloader.

That's a lot of boxes for 15 users!  And given that you have a Citrix Server in place, you don't really need the remote web workplace feature.   Not sure exactly what you mean by 46 nodes...you have that many workstations for 15 users?

Given the additional information, I'd change my recommendation.
Simply make the Windows 2008 server a DC, GC, DNS Server and DHCP Server (don't start it yet)
Move all your folders to the Windows 2008 server after all the replication is done for AD and DNS.
Then transfer the FSMO roles to the new Windows 2008 server and DCPROMO the SBS2003 server and then shut it down.

You cannot run the SBS 2003 server as anything other than a DC holding all the FSMO roles..it is a violation of licensing and it will start shutting down on you regularly

With SBS Essentials 2011, there is no Exchange, not an option to bring it back in house, with adding another server for that, because Exchange 2010 outside of SBS is not supposed to be on DC.

I may have mis spoke on the nodes.  

Well keep in mind that most of these users are hitting the SBS for our DOS based...yes I said DOS based billing app, and then another box for a web app that we've been working on for scheduling and patient info.  The 10TB Storage server is only used by 4 people and mostly only three as it is where two image capture devices send captured 3D data.  Huge files that have to be retained for 7 years as this is a required.  This data alone is growing at a rate of 1TB per year.  We're already at 3.3 on that box.

The Citrix server is ONLY used by the doc in the practice.  There were plans for other uses but it just didn't make sense.

So it breaks down like this:

SBS does it's usual functions of AD, DHCP, DNS etc.  Users folders are here, our DOS billing app runs here, my Ultrabac backup software runs there and is licensed for SBS.  There's also an old app that used to be used to file records in that there are 400gb's of Word Doc's in it.  We don't use it anymore.  However, we have to maintain that data for 7 years.  Although it could be moved to tape, it never fails that at least once a week someone needs something out of there, so I just leave it there and back up the entire SBS every night.   But the vast majority of activity happens on this server.

The Storage Server 2003 is the landing place for those huge image files I spoke of and our Vipre Enterprise Anit Virus.  It's 10TB's RAID 5 so about 7.5 or so usable and only 4Tb's available with that data growing at 1 TB per year, minimum.  It is backed up on the weekends, as it takes 22 hours.  Twice that long when the backups are encrypted.  Can't compress them and they all have to be backed up.  I do differentials to disk every night on this server.

Citrix box, Server 2003 is strictly used for that.  Only one user.

Another  Server 2003 box is about 2TB, RAID 5 that I use for running some of my back ups to and and putting stuff over there in "Legacy Land" as I call it.

The last 2003 server is where our in house web app runs which is being moved to the server I just mentioned due to size allocation.  So it will be freed up and unsused really at some point soon.

The new HP DL380 that I've installed Server 2008 on.  It has two drive bays used.....I want to say it's about 500GB. Nothing done other than install of 2008.

I"ve got 13 workstations, (Towers) all XP except two of which are running Win 7, 4 laptops 2 running 7 and the others XP.  2 credit card terminals, 2 networked printers, 1 networked C/S/F and a wireless AP for inside and one for guests that is on an interface of its own...192.....

So there's a snapshot of my network...it was a mess when I got there.  the other guy had 8 desktop switches laying all over the servers and rack rather than one managed switch like I have now in the Procurve 2900-48g.  There was a Sonic wall and that's been replaced by the Cisco ASA 5505 that to be quite honest is overwhelming to figure out at times.  You folks that speak in "Cisco" are on another planet!  I rewired and reworked everything a couple of years ago.  New UPS's and new power feeds to the server rack.  

Ah, rambling!  Sorry guys...

Any recommendations are much appreciated as in your world, I'll be a newbie for years to come.

Thanks

-Mac

You don't mention whether Server 2008 is 32 bit or 64 bit...you're DOS bit app is not going to run well, if at all on a 64 bit OS

If you're going to run the web app on the New Server, you don't want to make the new server a DC, bad

I would probably also move the word docs there and off the SBS server

SBS probably needs to stay for now..get that DOS app upgraded so it can run on Windows 2008, preferrably 64 bit

Then get yourself 1 big server with lots of RAM and you can probably do a lot of consolidation  If you think you want Exchange back in house at some point  Then SBS 2011 would be the choice

All great info here.  The server is 64 bit but thought of maybe leaving the DOS app on the old sbs as it is already there and functioning as it should.  

As for the web app, that will be running on a different server altogether.  

What I guess I was thinking was that I'd have the new 2008 64bit box do all the AD, DNS etc type stuff and leave the DOS app and a few other things on the old SBS.  You know, take that SBS out of the "critical" core role it is now.  

I have at times thought about virtualizing all other servers except for the one that houses 3tb's of images.  I just don't see that as feasible nor do I think the proprietary application that writes the image files to that server now, will play nice with it.  

But I could virtualize others, right?  Citrix server (only one person using that), my web app server for example.  

It really seems this network here could be a bit smpler but when you have to manage that much data for just a small office and retain it for 7 years while amassing minimum 1 tb per year on that server alone....well.....   we're sort of in between.  we're small but with a gigantic number of files and the vast majority of those are huge.  Seems it could be simpler though.

Still thinking...Love all the great info you guys have though.  It's almost too much at times!

Just remember if you do keep the SBS server that it MUST hold all 5 of the AD FSMO roles.

Ok.....Can I "demote" the SBS and allow the 2008 machine handle that?

No, the SBS server MUST be a domain controller and it MUST have all 5 FSMO roles otherwise it will randomly reboot.  You will also be in breach of licensing.

I guess that's why your rank is "Genius"!  Argh........ So I'm sitting here with this 2008 Server ready to go.  I really want to take that SBS out of being the "key" to it all.  I just feel a failure coming.  Been tooooooo long do we're due one I'm sure.  

Suggestions?  Or just leave it all be?  That approach doesn't seem as if it is the wisest as that's just waiting on something to happen and then fixing it rather than being better prepared.

Na, Genius just means I have answered more questions correctly than a Sage or a Wizard.
But....I have been working with SBS for a LOOOOOONNNGGG time.

Well....you are using SBS2003, officially unsupported (I think) back in April 2009 so you should really think about moving on.

You have my SBS2003 to Windows 2009 Migration guide and SBS2003 to SBS2011 Migration guide in my first post, they should get you through the migration pretty smoothly.

Ok so just to clarify, do you suggest migrating away from SBS or migrating to the latest version?  I only have 12-14 users, the Essential version would be fine, correct?  I could run this on the 64bit box I have now....I don't think in my vol licensing I have a license for anything other than 2003 and 2008 server editions.  I'll have to look.

Please forgive any "beating a dead horse" here.  Although I've been watching out over this network for 4 years, I've not had to migrate anything like the "core" of this.  So obviously I'm wanting to be as clear as possible.  

I really don't think I'm going to bring exchange back inside, although I'd like to learn about it.  I messed with it just enough to know when it got fouled up and would receive mail anymore that in my instance hosting made the most sense overall.

I would recommend moving away to the latest version of SBS, the Essentials edition is limited to 25 users and is designed around hosted services.  The other version is limitd to 75 users and has integrated Exchange. And to be honest, from a cost perspective it's a damn sight cheaper than client access licenses for the full product.

I guess it depends on what you want to do going forward?  Can you ever see yourself having more than 25 users/devices?  Will you ever bring your Exchange back in house?

If the answer to both of those is no then go for the essenials edition, if the answer is yes then go for SBS2011 Standard.

Well that is a no on both accounts.  Certainly not while I'm around.  That would mean doubling the staff and that just isn't going to happen.

As for exchange, I really haven't been sold on having it "inside".  I mean, we're 12 people, of those 2 there's only 2 that ever check their mail outside of the building anyway.  That's me and the doc.  But it's a critical thing for him.  I like the security of "Rackspace".  Would I like to "learn" it, sure...as I know it would benfit me.  

I think I'll go with the "essentials" version as you suggested, but my reseller just sent me an email saying it wasn't out yet?  That's not right is it?

Man you know a lot about this.  Do you manage a large network?

I manage lots of networks ;) Ranging from 5-6 users to over 2000.

Essentials is due for release very soon.

Whew that's a lot.  I think the essentials fits here.  What would be wrong with just starting clean?  Just get all the info off the 2003 SBS that I need, turn it off and install Essentials on my 64 bit machine?  Move that DOS app to another 2003 standard machine, or move it off and install 2003 standard on what is now my 2003SBS machine and put the DOS app back on it, rejoin it to the new network created with the SBS Essentials box and go from there?  There' s never been anything special about how this current SBS is set up.  No one has ever really done it "right", you know with true policies in place and permissions granted as they should be.  I've done those things bit by bit on my own as the need arose.  

The only problem would be the users etc.  You would need to set everything up again, all the security, user accounts etc.

That I don't mind.  There's only 12 of us.  So there's not a ton to do there other than put data from existing users folders where they new users folders are created, correct?  

As for security, this thing is a mish mash of policies etc.  When you install SBS, there are defualt security policies created, right?  Then you can add and customize from there?

Are you like sitting right over my shoulder reading what I write?  You answer nearly as fast as I can post!

LOL! That's made me laugh, no I am not, be handy if I was though right ;)

Yes absolutely, all you need to do is place the backed up data in the new shared folders and you are good to go.

Yes default policies will cover most of what you are interested in and you can add anything additional if required.

Damn right it would be!  This enviro I work in is a hodge podge of IT and medical, so I'm back and forth and learning on the fly, by mistake, with the help of really good IT friend and guys like you.  But you've made this make more sense overall.  But man when you read a lot of things it seems it's being made way more complicated than it needs to be.  Especially MS.  

I just want to get up to date, take advantage of a clean start and realize the benefits of starting "new" if you will.  This SBS I have here is the only remainder of the old IT firm that used to take care of things here.  The biggest hold up for years has been this damn DOS application.  This is how we send out our billing, over a fax line, everyday.  Now they are finally looking into the "new" version of this that is web based, like I've asked about for 2 years now!  That one thing has been a MAJOR roadblock for so many freaking things here.  It has basically tied my hands in many ways.  It being the lifeblood of where the $'s come from, I can' take a chance on that thing not being active.  As without it we're dead in the water.

When I do this, I can do my install and get everything set up and basically "fip the switch" over to the new SBS, right?  I realize I'll have to assign the IP addresses that are on the current SBS over there on the new one.  (Those given to me by my ISP.)  Right?  

One more belabored question.  Every device here is configured on the 10.0.0.x scheme except for my interface that I run my gues wireless through which is the 192.168.x.x scheme.:  do you suggest I rework that too at this point of change?  

We are here to help, and you will find those of us that do it day in day will say mostly the same things, and that helps for clarity.  What gets confusing is when you have 4 or 5 people in the thead saying different things.  If you post a lot here you will get to know the regulars and who you can trust the advice of.

You can install everything, copy all the data over and even setup all the users, what you will then have to do is manually disconnect the omputers from the existing domain then connect them to the new one using the http://connect from each compter and following the wizard.

Once your done just setup the new SBS server with the old address and you shouldn't have to change anything else.

There is nothing wrong with a 10.0.0.x and the wireless will be on 192.168.x.y for a) routing I suspect and b) security.  I would personally leave this as is, too many changes at the same time makes it difficult to identify where things went wrong if they do :)

Man that all sounds just like I've been thinking it should sound like.  I want to do as much of this as possible during the daytime hours as that's like 95% of the time I have available to me.  So getting a lot done until I HAVE to do otherwise would be ideal.

We are typically closed, (office not open to patrons) on Friday afternoons and there will be a couple days at the end of this month that we won't be "open" per se'.  Wonder if this "Essentials" is going to come out by then?  I could utilize a ton of that last week of the month to get this done.

I also have to talk to my back up software folks about relicensing my software for use on either the new SBS or for standard server box among other things.

Well saddly, SBS Essentials is estimated for release H1 2011, that could mean anything up until June assuming it's not delayed.  I haven't heard anything from the partner portal yet about a release date.

Shoot.......

But then on a plus point they did say February 2011 for SBS 2011 Standard and that was available in December ;)

Demazler, is it proper to have contact outside of EE?  Would be a great help to have your knowledge on tap if I run into an issue.

We are not allowed to solicit within a question thread but you will find contact details in many of the top members profiles ;)

gotcha thanks.  Im' going to close this thread by the way.  Ton of great info here and thanks a lot.  I just posted another question in the SBS primary zone about permissions on shares.  I have an issue that I can't figure out.  Thanks a bunch.  If you think you might be able to help on that one, by all means chime in.

Thanks

I'm just going to throw in here a little piece of software that is invaluable at its price: Beyond Compare from http://scootersoftware.com.

That has made data migrations so painless that you won't even notice they happened.

demazter

I need to start a thread about CHKDSK...what is the appropriate place for that?  

Depends.  You could appropriately place a CHKDSK Question in the OS Zone (Windows 2003 Server, for example) or in the Hardware/Hard Drives Zone(s).  Personally, I would do both.  You can choose up to three Zones, so do so.

DrUltima

Thanks Dru.  I just did that.  

-Mac