The first thing I noticed after building up the new server was the Server Manager screen that greets the administrative user on logon. I was impressed with the array of features that can be managed from this console as well as the breadth of the information about each feature that was presented. For instance, after installing DNS, the DNS service information and relevant event logs appear under the DNS feature in the Server Manager console.

The next thing that I noticed was that the new server would not reboot – it would simply hang on shutdown at a black screen interminably. At first, I thought this was the long shut down time that I was warned about. Apparently, there have been improvements made to the shutdown process that reduce the chances of file corruption due to services that fail to shut down completely before the allotted shutdown timeout period.

After a little research, I discovered that several devices drivers could not be found, including the one for ACPI. This meant that I had to be physically present to restart the computer after software updates and OS configuration changes. The test server that I’m using is an off-brand grey box, whereas major manufacturers like HP and Dell have probably already worked out any major driver kinks by this time. However, driver support is something to keep in mind.

After configuring a DNS server on the 2008 box, I installed Active Directory. As promised, the AD process runs as a service that can be stopped and restarted. This is convenient if you need to perform offline operations on a DC. As I explored around the AD tools, I noticed that GPMC was installed by default, so I didn’t have to download and install a toolkit to use it.

Once Active Directory was installed and running, I turned to the biggest new feature in Server 2008 – Hyper-V virtualization. Because it was early in the release cycle, only Hyper-V RC0 was available. Right away it was apparent that it was a 1.0 technology. Hyper-V only supported a few operating systems, and getting those few installed was far more laborious than on the other virtualization system that I’ve used. Many people have expressed interest in this technology, as it promises to save licensing money on virtualization. Stay tuned for an upcoming entry on Hyper-V, because the topic deserves a separate treatment. In the meantime, I recommend holding off for some basic features that are still missing.

Shortly after I had my test server configured just the way I needed to be productive, my activation grace period ran out. I attempted to activate my instance of Windows, but I received a message that the DNS server could not be contacted. I thought this was strange, since the server was a DNS server, and it could contact Microsoft without a problem. Once the grace period expires, basic Windows functions are no longer available, such as updating device drivers automatically. I could have reset the activation period for another 240 days, but this would only be putting off the inevitable.

After extensive searching, I found a Microsoft article that described the problem: “Activation Error: Code 0x8007232b DNS Name does not exist.” According to this article, my options were: a) set up a Key Management Server (KMS), b) use a Multiple Activation Key (MAK), or c) use the license key. Since this was a TechNet-distributed version of Windows, the TechNet site insisted that I did not need a key, and no key was made available. This only left the option of creating a KMS. To prepare for this, I began reading the extensive “Volume Activation 2.0 Resources for Windows Vista and Windows Server 2008.” It was here I discovered that until five instances of Vista and Server 2008 on unique hardware on your network made activation requests of the KMS, no requests would be approved. Here I was stuck, since I did not have five unique computers on which I could install Vista or 2008, just to get my test server activated. It seems that small businesses using TechNet for testing fell through the cracks of Microsoft’s new licensing plan.

After six months of using Windows Server 2008 on my testing server, I concluded that the OS is not mature enough to be worth the trouble of keeping it going in my situation. I do encourage others to try it out in a testing environment to familiarize themselves with some of the nascent features. I’ve rebuilt my test server with Windows Server 2003, and I’ll continue testing Windows Server 2008 as a virtual machine. I look forward to exploring and writing about the greatly improved performance logging capabilities, the new application virtualization feature in Terminal Services, and Hyper-V. Check back for more articles on these topics in the coming weeks. Meanwhile, the Server 2008 posters will continue to hang optimistically over my monitor.

The Backstory

We started out with Webcal.pl for 2 years, then “upgraded” to OpenXchange (which was terrible) for 6 months or so, then SugarCRM for the last 2 years or so.   Nobody was particularly happy with SugarCRM either, the interface was slow and buggy, and the interoperability with fat clients and devices never really worked out.  You could say that our commitment to open source was hurting us, because none of the solutions were successful business enablers.

The hype around Zimbra has been considerable.  Zimbra seemed to be advertised as the best open source based MS Exchange competitor. Although the Zimbra folks mention Exchange as little as possible, it is clearly where they set their sights.

Mini Review

Held at face value, the single most compelling feature for users is Zimbra’s Outlook-killer web interface.  The user experience is really fantastic, I’ve seen Outlook, Thunderbird and Apple Mail/iCal users drop their fat clients and switch to using the web interface exclusively.  It is just that good.   You really have to try it out for yourself to see cool things like the Gmail-style email conversation views, smart tags and calendar views.  The built-in IM functionality is a brilliant add-on as well.

But that’s not all.  The commercial version of Zimbra (which is worth every penny) provides an Outlook connector which provides an Exchange-like user experience that is nearly imperceptible to most users.  You can also purchase (as an add-on) over-the-air sync functionality for Windows Mobile, Palm and Blackberry devices (BES required).

Zimbra is also totally interoperable.  The web interface works under IE, Firefox and Safari.  Zimbra provides classic POP/IMAP/SMTP services for those that want to keep their old mail client.  Calendars can be accessed via the iCalendar protocol, and even exposed to other users as authenticated or open icalendar or free/busy feeds. The IM functionality is fully standards-based, and supports any XMPP capable client like Pidgin/Gaim, Adium or Trillian.

But is Zimbra right for you?

Every business needs Calendaring just as much as it needs Email capability these days.  In my opinion, business fall into 4 camps:

1. You have already invested in a recent version of Exchange or equivalent (Groupwise, Domino, etc)

Probably not.  You’ve already invested 5 or 6 digits worth of capital, if not more, to get to your existing platform.  If it’s running poorly, or seeing low rates of user acceptance, you may want to look at other factors first.  There could be architecture or user expectation issues that could be managed with outside help, if you need it.  You can consider a forklift to a better platform several years down the line, but a wholesale email/calendaring platform switch now may cost you your job.

2. You are running older versions of Exchange (5.5 or 2000)

Lets face it, most IT systems are fully depreciated within 3-5 years.  Microsoft has left you out in the cold with mainstream support.  Your server hardware is ancient and dying.  Or did you try to just move that aging email system to newer hardware?   You know who you are.

Upgrading to newer version of Exchange may not have to be a foregone conclusion for you.  The cost savings of migrating to Zimbra may be significant.  You’ll have to buy new servers, but those servers may be spec’ed a little bit leaner than you’d need for Exchange.  You’ll need to retrain your admins anyway.  The big issue is:  Are you prepared to start running Linux servers?   If you’re a blue-blooded Microsoft shop with absolutely no Linux experience or aspirations, Zimbra is probably not for you, Linux (or MacOS X server) is a requirement.   If you think that you can train (or hire) some Linux talent, and pull it off, you will be loved by your users and management alike.

3. Those that currently run an open source based system (Postfix, Sendmail, etc + Sugar, webcal,etc)

What are you waiting for?  Seriously, you’re probably holding your users back from having proper calendaring and scheduling, AntiSpam and AntiVirus filtering (unless you’re running AMaViS) or internal IM functionality.  Go forth, and download the “Network Edition trial”.   If you decide that the $399 “starter edition” or $35/user pricing is too expensive, let your license expire and it will automatically fall back to the open source edition functionality, disabling Outlook/mobile integration.

4. Those that currently have a hosted/outsourced solution

If letting someone else run your Email server doesn’t give you the heebeejeebies, check out the long list of providers lining up to do hosted Zimbra, which tends to run cheaper per-mailbox than hosted Exchange.

My Only concern about Zimbra is…

Yahoo and Microsoft.   Last year, Zimbra was acquired by Yahoo.  So far, Yahoo has let Zimba flourish, but all of this may change if Microsoft gets its hands on Yahoo.  We thought the threat had passed, but recent news shows that Carl Icahn is launching a proxy battle to replace Yahoo’s board with a more Microsoft-friendly one.

What do you think Microsoft is going to do if it purchases the new single biggest threat to its very profitable Exchange product?  I don’t think anyone who’s been following Microsoft’s decades of brutal predatory takeovers and monopolistic business practices is expecting Zimbra, its staff and any patent portfolio to survive in one piece or be spun off.

The fact that large parts of Zimbra is released under the GPL may not help.   Microsoft may try threaten patent lawsuits against Zimbra’s customers as well as any business that sprouts up to support the GPLed version.  They’ve done it with Linux, remember that they funded Baystar which funded SCO’s lawsuit against IBM, Novell, and a few large Linux customers.

Just to be clear, I’m not saying that the threat of Microsoft takeover should ruin the the taste for Zimbra.  Just be smart, and keep an eye out for the writing on the wall.

-Irving Popovetsky

Principal Consultant, ProStructure Consulting