Moving on from sbs 2008...

Are there any realistic tools out there for planning an exchange environment?
I currently have approx 30 users, & am looking at the end of life for SBS 2008 & am trying to determine the best route to go.
I seem to have heard that M$ really wants you to have 2 exchange servers, which may be fine in a 100,000 mailbox environment, but not a small one like mine. There are other considerations, as well, as my other servers (T110 II, 2008 r2 std, basically for remote access to quickbooks & a T100, 2008 std,  that's a bdc) may need to be upgraded as well & I am not wanting to bust my IT budget! I know some argue that it's best to keep everything under my control, but my environment is not a high maintenance one.
Any advice appreciated!
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Patrick BogersDatacenter platform engineer LindowsCommented:

Two paths you can choose from, office365 for around $5-10$ per user per month or keep the on premise.
 Here you could choose for a more recent version for E.g. Sbs2011 or you can go full blown exchange, it depends budget.

I recently did a move of this sort for a client and can provide one perspective.
I looked into what it was going to cost for Exchange (including software and upgraded hardware) and concluded that moving to Office 365 for email ($4/user/month) was a better choice.  I was dealing with only 12 users so the decision was easier than with the 30 users that you have.

I set up a new server with Server 2016 as the host and 2 Server 2016 VMs.  As I read the licensing rules, as long as my host doesn't do anything but host the 2 VMs, one Server license is adequate (if you go this route confirm that this is correct).  One VM does DNS, DHCP, and is the Domain Controller.  The other VM does file hosting and is the QuickBooks server.

The move to Office 365 went fairly smoothly once I realized I had to tell workstations how to ignore the SBS for email during the transition.

This approach worked well for my client.  Your greater number of users may tilt the decision otherwise.

What features in Exchange are you using other than basic email services?  If nothing else, consider an external email host which should cost around $150/year total for all users.  That was ruled out in our case as the client needed to share calendars.

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I am working on a similar project as well.  After doing the breakeven cost analysis we determined that Office 365 didn't make sense.

For this specific client, on premises Exchange will be "free" after 3.5 years where Office 365 cost is pretty much constant ever year (providing they don't increase the price).  You may want to do your own breakeven cost analysis to see if Office 365 makes sense for you.

If migrating to Office 365, it comes with the synchronization tool and support you need to make the migration easy for you.  See technet article "Step-By-Step: Migrating from Exchange 2007 to Office 365"

As for on premises Exchange there are tools such as Netmail, ADManager Plus to help you with Exchange migration but for an environment of 30 users it's hardly worth trying to automate the email migration.  It's additional time to learn how to use the tool plus software cost.  It's easier to just export each mailboxes to PST then import them back to the new Exchange server.
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gromackAuthor Commented:
Yes, licensing costs are/were another factor, as when I first started pricing this out, it seemed that approx half of the cost was licensing alone! I have zero experience in the VM world, but this isn't a high maintenance office, they basically want QB & email to work. Not using shared calendar or even a shared address book in exchange,
Scott SilvaNetwork AdministratorCommented:
If all you are doing is email you could do a Linux based e-mail server for much less, basically the cost of the hardware...

There are several fairly ready to go mail appliances out there.

Just a coupe out there...
"they basically want QB & email to work. Not using shared calendar or even a shared address book in exchange,"
If that's really the case (and you don't expect it to change in the next few years), then I'd look seriously at outside email hosting.  I use but there are plenty of reliable hosts out there who will do it for about $150/year.  You'd be able to have all the email addresses and aliases you want, access the email by POP, IMAP, or a web interface, and would even get FTP and web hosting (that you don't have to use).

I agree that with 30 users it may be easiest to move the mail manually.
gromackAuthor Commented:
site5 has got to be the worst company I've ever dealt with. One of my other clients use them & they were blocking mail from one of their clients,  somehow it was on a spamhaus list. Checking spamhaus showed no problems with blocked sender, though.
Sometime as long as 4 or 5 days to get a response out of their online support!
It took over 3 weeks to resolve issue!
I keep seeing something on Twitter about them, recently being taken over by another company & support has gotten even worse?
gromackAuthor Commented:
No truth to the story that M$ tries to push you towards two servers, a front end & back end one?
Scott SilvaNetwork AdministratorCommented:
I don't think 2016 lets you run main server and edge on the same hardware, but I think that is it...
 You usually need edge if you are running anti spam and such from Microsoft
gromackAuthor Commented:
I've been using barracuda for spam & virus filtering, which brings me to the question,  if I went with 365 or exchange hosted, do they do any spam & virus filtering?
Cris HannaSr IT Support EngineerCommented:
Call barracuda...they do Office you'd get the hosted email...just the basic plan...and continue to get all your protection.
gromackAuthor Commented:
The thought of hosting a couple of servers in a VM setting has always made me nervous, as in what if the host goes down? That, coupled with the lack of my knowledge & experience with them, is making me shy away from t aht route. Owner of the company seems set on keeping it in house & at this point, money doesn’t seem to be an object. I really didn’t want to go with SBS 2011, as its already 6 or 7 years old, either.
I remember when upgrading from SBS 2003 to 2008, I used a company called sbsmigration, since you couldn’t have 2 sbs servers in network at the same time. How difficult is it to remove a sbs from a domain? Also, with going 2016, I’m guessing I’ll need to upgrade other servers, as well. Is anything I have worth keeping?
Sorry, my first client I ever had was a penny pincher & has burned that into my firmware, haha!
Cris HannaSr IT Support EngineerCommented:
sbsmigration is still very much in business
You won't find SBS2011 at least in legal, license-able state, so you can forget that

Your best bet for 30 users where you are not doing collaboration, just email is the low-end Office 365,
The good news with Office 365 is you'll never have to do a migration again.

If you need remote web access...then the best bet is Server Essentials 2016 and you can do it all physical on one server.  Otherwise standard server 2016 (where you could still have the Essentials role)

I think having Exchange onsite for less than a couple hundred users not using collaboration is just not good use of the money.
gromackAuthor Commented:
What about 2012 vs 2016?
I am going to try to convince owner to go with Office 365.
Keep in mind the 25-user limit with Server Essentials......

Unless there is some very compelling reason to go with 2012, 2016 should make more sense.  It will be under support longer and may avoid some future compatibility issues.

As far as migration goes, it's not all that difficult and you should be able to find online-guides.

"I am going to try to convince owner to go with Office 365."
Carefully consider if that makes economic sense if all you want is email.  If you think that the other features of Office 365 would be useful in the future, it may make sense.  Otherwise, I'd go with a host for POP/IMAP mail.  I mentioned site5 as someone with whom I've worked, not as a specific recommendation.  (While I had excellent luck with their support in the past, my most recent encounters were not good.)

If you compare Office 365 to Exchange, you'll find that the big issues have to do with cost.  Exchange will have a mostly known cost (other than ongoing maintenance) that is generally all paid up front.  You'd need to count the cost of Exchange, CALs, and hardware costs.  Keep in mind that the hardware cost could just be buying a better server to allow another VM.

With Office 365 the cost is pretty well fixed (unless the price increases), but you will pay every month and for each user.  For a small number of users, this can be the better approach.  As your number of users grows, the cost benefit of Exchange becomes more apparent.
gromackAuthor Commented:
Going with 2016 would also require me to update my 2008 r2 servers, as well, right?
If I were to pass that 25 user limit, is there a type of in place upgrade I could do, like the unlocking features option in win 10?
Cris HannaSr IT Support EngineerCommented:
The SKU has a limit of 25 users and 50 devices
But if you go with Standard and add the Essentials role, there is no limit

Why would you need to update your 2008 R2 servers?
There is an upgrade path from 25-user Essentials to Standard.  I've not done it though I'm told it is pretty straightforward.

You mentioned hesitation about using VMs.  Even with a single server, I'd suggest looking carefully at doing it as a VM.  Among other benefits, it will give you much easier portability if you need to move to a different physical server.
gromackAuthor Commented:
I thought I had read some where that in a 2016 domain, other servers had to be 2012 or 2016 - is this not the case?
I did like the option you had recommended, now that I think about it;
I set up a new server with Server 2016 as the host and 2 Server 2016 VMs.  As I read the licensing rules, as long as my host doesn't do anything but host the 2 VMs, one Server license is adequate (if you go this route confirm that this is correct).  One VM does DNS, DHCP, and is the Domain Controller.  The other VM does file hosting and is the QuickBooks server.
Then I could offer the exchange vs 365 option, after that.
Cris HannaSr IT Support EngineerCommented:
You can add a Windows Server 2016 as a DC to an existing network without upgrading everything else AFAIK

Keep in mind you cannot install Exchange on a DC
I did a different upgrade from Server 2008 or 2008R2 to 2016 Essentials without any significant AD issues.  They were both in the same domain.

You may want to consider setting up DFS on the existing system before the migration.  You can use it to centralize the assignment of shares such that it will be easier to move them to a different server.  It won't really save you any effort this time, but will if you do another migration at a later date.
gromackAuthor Commented:
And what about the licensing for all this? Will the 30 exchange CALs cover everything, or will I need additional ones for my 2 VMs?
Cris HannaSr IT Support EngineerCommented:
You would need Windows Server CALs (which ever version of server you go with) for EACH VM and Exchange CALs for which ever server Exchange is on
"You would need Windows Server CALs (which ever version of server you go with) for EACH VM"
I've been under the impression that licenses apply to the network across all servers.  For example, if I have 20 users and 2 servers, I only need 20 user CALs.  Have I been mistaken or has there been a change that I missed?

Of course, one should get licensing answers from Microsoft to be sure.
gromackAuthor Commented:
And going even further, you'd think an exchange CAL would 'include' a server CAL, since you're not going to have exchange without the server!
Cris HannaSr IT Support EngineerCommented:
If you want "one cal" to cover all servers including Exchange, you have to buy CORE CALs
Will cover all servers and exchange
You can find out more about licensing CORE CAL SUITES here

CDW has these
gromackAuthor Commented:
No mention of Remote Desktop services?
Quite an array of prices there, too - should I assume they'd be in the $85 ea range?
Cris HannaSr IT Support EngineerCommented:
You'd need to call for price quote based on what you'd qualify for.   but I'd say that's about right

As for remote desktop...if you enable the Essentials Role, you get Remote Web Access without additional license requirement
gromackAuthor Commented:
And the essentials role is an option on 2026 essentials? I know that sounds like a stupid question, but I can totally see M$!saying, 'so you want the essentials role with your 2016 essentials, that will be extra'.
And I've seen something about Remote Desktop , azure & sql - that's just another option, right? I'm not going to need all those to run Remote Desktop, will I?
Jeeeez! I really should keep up!
Cris HannaSr IT Support EngineerCommented:
The Essentials Role is added via Server Manager on Server 2016 Standard Edition
No, it's not extra
gromackAuthor Commented:
One phoen with Dell, who is asking me how many CALs I'm needing, on each server?
They are claiming that the CORE license doesn't work like an all encompassing license & are even asking how many remote desktop licenses I'll need?
Cris HannaSr IT Support EngineerCommented:
Then I'd call CDW.  Not always thrilled with Dell for volume license questions
gromackAuthor Commented:
Jeeeee-zus! Even CDW telling me I'm going to need. Remote Desktop licenses at $120 each. And the whole licensing per core I really don't get, either. All CPUs I'm looking at have 4 cores, but OS licensing is 16 cores?
Are you saying you will have 4 CPU with 4 cores each?  From what I understand MS server license is for two cores per license so for a total of 16 cores then you will need 8 qty. of licenses. Again, verify with a different vendor other than CDW, licensing structures changes all the times so don't quote me on it.
I believe that the 2 cores/license is correct, but keep in mind that the cost of these licenses is about 1/4 what they cost when one license would work for 2 quad-core CPUs in one computer.

I believe that you are correct at needing 8 licenses for 4 quad-core CPUs.

Of course, licensing questions should really be run by Microsoft.
gromackAuthor Commented:
Thanks to all, I'm sure I'll be back with more questions as I move forward with this!
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