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Upgrade suggestions for upgrading from SBS 2008 and Exchange 2007

I want to look at upgrading our email and server(s) and wonder where is the first place to start that is simple, for starters.  We currently use 3 servers:

1-SBS 2008 is the DC and has Exchange 2007
2-A second server runs SQL Server 2008 on a Windows Server Standard SP2
3-A third server is our web server on a Windows Server Standard SP2. We have clients and vendors log onto a web page, not sure how that affects certificates or whatever.

We have 7 employees, will have 8 or 9 in the foreseeable future.

All the workstations are Win7Pro and run Outlook 2007 (and other MS Office 2007 Pro programs, but we really only use Excel and Word occasionally)

Is it as simple as only upgrading to MS Office 20something, or, do I have to also upgrade Exchange to 20something, or do I also have to upgrade all the server OS's, too?

One more thing, I don't want to waste time discussing putting our stuff on the cloud, especially our email.  Very wary of outside entities, I do not trust Big Brother with our stuff, so, prefer to keep it all in house.

I would like to install the first set of upgrades before year end.
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Obi WanFixerUpperCommented:
SBS2008 is a great product as you get a huge mix of features:
  • Domain Controller
  • Exchange
  • Sharepoint

SBS 2008 Premium also gives you a 2nd windows server to run and SQL server

Since SBS has stopped being made, you either need to buy full version exchange, and SQL and server, & buy Client Access licenses for them all,

Or move email to the cloud (Exchange Online) with Windows Essential 2012 R2 server (No Client access licenses required), and get the free version of SQL if your databases are small enough (Under 12GB i think)

I get the point about not wanting "Big Brother" to view your email, but thats a pointless worry these days if you look further into it.

Much cheaper moving email to the cloud than buying exchange for on premise.

Besides, you get 50+ GB of email storage per user and a highly availible platform as opposed a single exchange server on premise.

Good luck planning it out, the above should give you grounding for the investigations:


wfcrrAuthor Commented:
Do I only need to upgrade Exchange if only upgrading MS Office to something newer?  I purchased SQL Server 2008 a few years ago, as the version that is included with SBS 2008 won't support our custom application.  I have no problem keeping SBS 2008 and Windows Standard Server in use, just wondering when it goes out of support for updates.  

So, to upgrade MS Office to something more current, sounds as though Exchange has to be upgraded?

Regarding outside entities snooping our email when on cloud, where can I read about it is a pointless concern?  Sounds a little too good to be true. I think having email on our server means the only way to get to it is to hack it, where as on the cloud, my instinct is that whoever hosts our email can look at it all they want, you know?  I can't really understand how another entity can have our email on their space and not, in some way or another, gain access to our email.
AmitIT ArchitectCommented:
If you don't have budget constraint and have skills to manage on-premises exchange, AD and SQL. Then there is nothing better then having on-premises server. You have more control, more option to customize and expand.

Also, in long run, on-premises might be cheaper. As cloud vendors are not at all cheap. Until you take top level plan from cloud vendor, you might not be getting much from them. Several plan from MS also doesn't have email solution.

As far as migrating from current server. You need to look into migration steps for each component. Like Exchange, SQL etc. For Exchange your best option is 2013. Which you are start from here.
wfcrrAuthor Commented:
Thanks for that link. We have been able to manage the on-premise servers using our programmer and a consultant.  What I may need to do for the migration is hire a different consultant to get us set up.  I wonder if hiring someone on EE is a good idea?  I can handle whatever a consultant needs on-premise so that he/she can remote in and do their set up and migration work.
AmitIT ArchitectCommented:
You can create GIGs request in EE.
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