SBS 2003 to SBS 2008 Upgrade recommendations

Hi Experts,

We currently have SBS 2003 with 16 users.  I bought new servers... SBS 2008 Standard & Server 2008 Standard.  SBS 2008 will be for AD and Exchange.  Server 2008 will be the application server.

I have decided to go with a clean install instead of migrating unless you would recommend otherwise.  Reason for this is I am moving all applications including BlackBerry Professional Software to Server 2008

I have several questions regarding SBS 2008:

1)  Should I keep the same domain name?
2)  Should l keep the same computer name?
3)  Exchange - Should I just export everyones mailboxes manually to PST, then import?
4)  Is there any affect in my organization using different usernames (ex jeff on sbs 2003 jlastname on sbs 2008)?
5)  After SBS 2008 is up, I will have to disjoin the 16 workstations, then rejoin them to sbs 2008.  Anything I should be aware of to retain all personal settings (desktop, favorites, my docs)?
6)  Any registry changes need to be done on the workstations?
7)  Any other advice or articles that would help?

Thank you experts.  Sorry for all the questions within 1 question
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ArmenioConnect With a Mentor Commented:
That depends  on your reasons for wanting to start over.
Personally i have done a few 2003 to 2008 exchange migrations and only had one fail but that ws a dodgy set up to start with.

I have found the migration to be relatively reliable and less work than doing it all from scratch  also the migration is really only the domain settings  exchange and all the configuration. So it does not bring  over pre installed programs so you will have to reconfigure things like blackberry server separately.  

The migrating works buy modifying the registry for I think 21 days and allows a second PDC on to the network, were it then replicates all the data  as if you had a standard server and a couple of PDC replicating across the domain. once it had replicated all the data it then kills the old SBS effectively demoting it from PDC. and then activated the new SBS08 as the only PDC allowed in the SBS domain.

I would strong recommend using the migration as it is how ms intended it to work has good wizards and there is a full document on how to do it.  and some extra info and some watch outs Note please be sure to read the whole document before starting as I found some things are at the end of the document that need to be done at the beginning. Like make sure the exchange limits on the new domain are larger than the largest mailbox on the old domain els it screws up  

most importantly have a full backUP  id recommend shadow protect evan the trial will do perfectly for this purpose just install the sbs version and use a large usb hard drive  to take a full back up this is an awesome bit of software that will give you a month trial back up to an image and you can always restore the server to before the migration and nothing will have been broken.

little note make sure both sbs servers are fully updates with all patches before starting and again reread the full instruction before stating as i found some things to be in the wrong place .

The beauty of the migration is that once you are done everything pretty much works not need to rejoin pc's set up account importing mail all just works  also note it can take hours to migrate like the exchange part i leave over night and look out for the settings that just skips mailboxes it cant migrate  as you can always do them latter or manually .

extra reading
the migration document

extra watch out for stuff

let me know how it goes feel free to ask any questions

Please rate this as I'm new to the posting help parts and need all the feedback i can get to up my rating thanks --<<(( shameless self promoting))>>--
Cris HannaConnect With a Mentor Commented:
I'm not sure why you'd want to create all this extra work for yourself but if that's your choice, your steps appear to be pretty solid.
I would encourage to you to get the SBS 2008 server up and running for a week or two before moving workstations.  Get all updates applied to the servers, resolve all errors in the event logs and so on.  Much easier to do before it's live.
If you'd like to reconsider migration I have two sources you should consider   Philip another of the SBS MVPs from Canada and has put together this exception guide.
If you'd like to migrate with even more hand holding visit which is owned and supported by Jeff Middleton, and SBS MVP who lives in the US and provides 90 days of support with his product.
itechresultsAuthor Commented:
Thank you both for your suggestions.  That was what I was looking for, your opinions.

My reason for wanting to start over is I'm not comfortable with the migration process.  I have read numerous artiles and posts with the horrors of migrating.  I have never performed a migration and am strapped for time (my fault). I can't afford to lose a day or 2 with having to start migration over.  If I am strapped for time you'd think I go for the migration process!

My plan was to get the 2 servers up an running this weekend, patch and configure as much as possible (installi the apps, set up users, policies, etc.)  Then the following weekend, transfer data, finish configuration,  join workstations, etc..)

I am interested in possibly exploring  I read up on the website and it looks quite helpful.  Looks like I would need a spare server...really don't want to jack with the 2008 standard server (my other new server).    CrisHanna, do you know if I can use a spare desktop or am I crazy?  Just curious, but I will be contacting them for specifics

I found your comment to be very thorough and informative.
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itechresultsAuthor Commented:
Eventhough you both are in favor of migration, would you mind giving me your input on how you would go about starting from scratch?  I know CrisHanna touched on this, but I guess I'm looking for some more detail like steps, a guide or informative article.
Cliff GaliherConnect With a Mentor Commented:
Not an answer to your latest question, but it is an answer to your initial reason for wanting to start over:
Starting over will actually take more time than a migration *even* if you lose 2 days because you had to start over. Fresh installs just take that much longer when all is said and done. My answers to your initial questions should illuminate and illustrate why:
1)  Should I keep the same domain name?
Does not matter. This is a new installation regardless. Internally windows uses GUIDs and SIDs for various tasks, so the visible name rarely has any meaningful connotation beyond what you attach to it. If you want to keep the existing, go for it. It won't make the new install process easier though, so if you want to change it, go for that instead. COMPLETELY your preference.
2)  Should l keep the same computer name?
See answer #1. Same loginc applies
3)  Exchange - Should I just export everyones mailboxes manually to PST, then import?
You will *have* to do so if you aren't migrating.

4)  Is there any affect in my organization using different usernames (ex jeff on sbs 2003 jlastname on sbs 2008)?
Answer #1 again applies. Usernames, even if kept the same, will internally be different from a security/permissions/ACL perspective. Keeping the same names gives you no advantage.
5)  After SBS 2008 is up, I will have to disjoin the 16 workstations, then rejoin them to sbs 2008.  Anything I should be aware of to retain all personal settings (desktop, favorites, my docs)?
Yes you will have to disjoin and rejoin. You can use tools such as USMT or windows easy transfer to retain most settings. You can even try copying profile folders to retain even more settings. Neither is 100% and the latter is certainly not foolproof. Done improperly (and since ACLs will have to be reset), you can even compromise your new server's security if you aren't thorough. For the record, this is where a migration saves you SIGNIFICANT time and hassle.
6)  Any registry changes need to be done on the workstations?
Impossible to tell. Since this is a new domain, changes that were specific to the old domain may need to be manually rolled back. Disjoining the old domain will resolve group policy settings, but if there were custom settings pushed out, those may have to be repealed by hand. We don't administer your environment so there is no way to be certain. Again, this is another place where a migration saves you this hassle.
7)  Any other advice or articles that would help?
Clearly my advice is to reconsider migrating. Beyond that, I have none to offer.

itechresultsAuthor Commented:

Thanks for clarifying.  I think it's setting in and I'm seeing the big picture and should reconsider my strategy.

I will look into  and/or ms migration

Cris HannaCommented:
it's and the process is called a Swing Migration.   If you decide not to go with sbsmigration and try the MS route...make sure you use the Migration Guide from Philip Elder..also and SBS MVP, found here in conjunction with the MS method
itechresultsAuthor Commented:

I ended up using the Swing Migration from Jeff Middleton with great success.  I would highly recommend utilizing swing migration from  The great thing about Jeff's method is there are no changes or time limitation put on your production DC you are migrating from.  Jeff's instructions are very detailed and easy to follow.  Just pay attention and don't skip over any information.
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