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Windows 2003 vs Windows 2008? (Which is recommended and will I encounter any issues?)

I am in the process of having a new web server set up and I have the option of using Windows 2003 or Windows 2008 (platform).

I am not sure as to which would be recommended at this point in time?  Being that I will be placing files, etc. on this server that I won't want to have to move in the future .. (for quite a while) I was leaning towards 2008 (only because it is newer).  But .. I am curious as to ...

1. What are the primary differences (pro and cons) between using Windows 2003 server as opposed to Windows 2008 server (for website hosting, etc.)?

2. What are the benefits (if any) of Windows 2008 over Windows 2003 .. and visa versa?

3. Is it likely or possible that applications written in ASP, ASP.NET or PHP as well as other Windows components like ASPEmail, ASPUload, PHP 5, MySQL, etc., etc. will give me any problems when installed and running on Windows 2008?  Or is any version of Windows 2000 or higher going to be okay?  Let me know if I might experience issues (from what you know) and maybe what it is about Windows 2008 that might cause problems (if it will)???

4. Looking ahead, if you had to select a web server to begin setting up and using at this time, would you recommend the older Windows 2003 server, or would you recommend (and why) to move ahead and begin now with Windows 2008?

Let me know what you think and know about the comparison between these two.

Gary Gordon
Gary Gordon
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1 Solution
1. Windows Server 2008 offers improved features, better security, new components and a huge range of other benefits over the older Server 2003. You get the benefits of IIS 7, which is improved when compared with IIS 6, and it is the most secure edition of Windows Server yet released, due to a reworked OS core and a lot of other new design changes.

2. The benefits of Server 2008 is that it is economically feasible to invest in it now, since using it now will leave you in good place for at least the next 5 years, until the next Microsoft server OS is released. The benefits of remaining with Server 2003 are that you have a proven, reliable operating system, but you might need to upgrade it sooner.

3. ASP, ASP.NET and PHP applications should work with Server 2008 once those components are installed, but there are still a lot of issues with components such as ASPMail and other ASP add-ons which aren't server 2008 compatible at the present time.

4. If it's for production use and could potentially be responsible for earning your business a lot of revenue, then I would stick with a Server 2003 machine for the time being, just because I know it is reliable and has been proven to be a reliable OS. Only once Server 2008 has been out for upwards of a year and there are starting to be good reviews and comments go around about it would I consider switching across to Server 2008

One big benefit of using windows server 2008 is built in support for virtualization. This version of windows will run your virtual machines in lot more efficiently. (of course you need to have the processor support virtualization at this level)

If you are not going to run web sites build using PHP I do not find any other compelling reasons to use IIS 7 (2008 server) other than this is a new version of OS and expected to more secure and reliable.

Using standard rule of thump for any Microsoft product wait until SP1 get released if your organization conservative. If you are stay in the cutting edge of technology then moving to 2008 make sense.

hope this helps
Gary GordonWebsite Developer, Designer, SEO and Online Marketing specialist.Author Commented:

RE:  ASPMail and other ASP add-ons which aren't server 2008 compatible at the present time

I am running apps such as:

Persits products such as ASPEmail, ASPJpeg, ASPUpload, and ASPXload
Perl (newest)
PHP (newest)
SourceGuardian (decrypter of encrypted php files)
ZendOptimizer (v3)

I am hoping you might be able to tell me if any of these would cause me issues.  And if so, why and is there any way I could use Windows 2008 and not have problems with any of the above?

I am leaning to wanting to use Windows 2008 only for the fact that I don't want to find myself needing to upgrade in 2 or 3 years.  I'd rather do it now.  My biggest issue is knowing that my apps will work .. and making sure it is a stable environment.

Are there any reports or comments from other users that would indicate that Windows 2008 is not stable enough to use for a "production server" at this time?


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I've actually got Server 2008 in production for a client, and it certainly is a very reliable server system. I just worry that if you wanted it to be doing a lot and if you rely heavily on it, then you should be looking at something more trusted and proven. If it's not something so critical it could ruin the business if it goes down, then you probably could look at server 2008.

I have heard on the grapevine that CDO and some of the ASPUpload applications are currently having issues with Server 2008. Without going direct to the companies who produce all your add-ons, I can't give you a straight answer for each one as to whether they currently have Server 2008 support or not.
Gary GordonWebsite Developer, Designer, SEO and Online Marketing specialist.Author Commented:

Do you have any idea as to why some of these apps aren't working with 2008?  Do you think it's something that the developers of the apps will have to update before it works or do you think it's more of a patch that Windows 2008 needs to come out with in order to correct something on their end?

The major OS core difference between Server 2003 and Server 2008 (the same difference as between XP and Vista) means a lot of applications aren't compatible with new features, such as security features, introduced in Server 2008. As a result, there are quite a few applications which have known issues between themselves and Server 2008 at present.

The best method to check if the apps will work - short of contacting the publisher - would be to use a Virtual Machine and the Microsoft-provided Server 2008 evaluation software to test them yourself. If you can get things working, you'd be good to move to Server 2008 in my opinion.

The updates to the programs must be added by the publisher of the app - Server 2008 cannot be "patched" as such to make the faulting applications work, purely because doing so would remove all the new security and other features - and years of work and investment on Microsoft's part.

Gary GordonWebsite Developer, Designer, SEO and Online Marketing specialist.Author Commented:
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