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Upgrading to IIS 5
FAQ about Installing IIS 5
by Brett Hill

There are at least two scenarios we are concerned with, one is upgrading an existing IIS 4 server (and maybe even IIS 3 for some of you slackers). The other is installing a sparkling fresh IIS 5 server from the start.

In both scenarios, we start in the same place - installing IIS 5. You can install W2k on an NT4 server with IIS running and it will upgrade your IIS server to IIS 5, however, that is not the recommended scenario. Some admins have done that with no trouble, and it is in fact the easiest way to get there for some, but many IIS 4 boxes are more or less a patchwork of user accounts, permissions, add-on software, hardware drivers that have accumulated from day 1, etc. Your chances of having problems are much greater if you "upgrade" your server vs. doing a clean installation and "migrate" your server. This is not just about getting IIS 4 to IIS 5, but getting NT4 upgraded to Windows 2000.

Now for the FAQ about IIS 5 installs (pay special attention to the bolded parts).

IIS 5 cannot be installed on NT 4. No way, no how.
If you install IIS 5 on W2K Professional, you still get a baby IIS that is limited to 10 connections. You can use ASP on it though and I know this is a popular development platform.
IIS 5 is part of the main W2K distribution CD. There is no Option pack CD.
Index server is now integrated into W2K and is installed by default when you install W2K. You do not need to install Index Server anymore, it's already there.
Generally, you install IIS 5 during the W2K installation. During an attended installation, a screen will appear showing Windows components to install. IIS, Index Server, and Front Page Server Extensions (FPSE) will be selected. Do NOT install FPSE unless you need them. If you don't install IIS 5 with the W2K install, you can easily add it later with add/remove software. Finally, if you are upgrading over an NT4 installation, IIS 5 will not be installed by default, but you can add it afterward.
You cannot select the default locations for IIS during the installation. This is different than IIS 4. The only way to do change the default location is to use an answer file and do an unattended installation. This means that if you format your system partition as FAT, you are really hosed. You can find more information about unattended installations in the Deployment Planning Guide of the W2K Resource Kit. Also, there is more information on unattended setup in the "Microsoft Windows 2000 Guide to Unattended Setup." This can be found on the Windows 2000 installation CD-ROM. You see it, extract the Unattend.doc file from the \Support\Tools\Deploy.zip folder.
You cannot prevent IIS from being upgraded if you are upgrading to W2K from NT4 or OS running PWS.
The IIS 5 Resource Kit is part of the W2K Resource kit. You really need to have those tools. Makes an excellent excuse to subscribe to TechNet which is about the same price is the Resouce Kit alone, plus you get ALL the OS Resource Kits, KB's, etc. I'm not a trying to sell you anything, but you could pay $299 for the W2K Resource Kit alone (at Amazon.com) - or - you can buy TechNet for $299, well - you figure it out. Truth be told, I got my W2K Resource Kit for about $120 after rebates and a good deal at pczone.com. Call me old fashioned, but I like have the hard copy.
DO NOT USE METAEDIT 2.0 which comes with the W2K Resource kit. It has a bug that can trash your metabase. You can however, use metaedit 2.2 for both IIS4 and IIS5. Strongly recommended. (See IISANSWERS home page under essential links for the download page)
IIS 5 does not require CALs (client access license) for anonymous connections. A CAL is required for any authenticated user other than anonymous.

There is a special issue regarding CALs and anonomous SSL connections. Originally, it was stated (and is till in some Technet documents like http://www.microsoft.com/technet/iis/iisdtcom.asp) that you the number of anonymous SSL connections is limited by the number of CALs. This however, is evidently not what Microsoft intended, although it is true that IIS 5 enforces this limitation. You can find a work around and a hotfix on KB article Q25329.

Little known but very useful tip: A detailed log of events that occurred or failed during the IIS 5 installation is kept in \Winnt\iis5.log. If your server isn't working, this is a good place to go and get info on possible problems that may have occurred during installation. An article on reading the log can be found here.

Also, after upgrading from IIS 4, you may need to edit the metabase as detailed in http://support.microsoft.com/support/kb/articles/Q248/3/50.ASP to enable Kerberos.

These tips come from a Technet IIS chat regarding upgrading some potential problems upgrading IIS 4 to IIS 5:

IIS accounts are not added to default Dcom access permissions. This was done because NT requested it to improve security
Some MTS packages might be removed from COM. This will happen if the threading model is not supported, or if the package uses PageOnEnd.
Some MTS packages might be unregistered, but will still appear in the COM manager. These need to be manually re-registered.
If you choose to "Upgrade my file system to NTFS" during the upgrade, your permissions might be messed up after the upgrade, causing ASP pages not to execute, Add/Removes to fail.... Go to the root drive, and change the ACLs to System:Full, Administrator:Full, Everyone:Read, and make sure those permissions propagate to Inetpub and WWWroot. Inetpub should NOT inherit from the parent, but WWWRoot should.
If Out of Process or Pooled Process apps don't work, but In Process ones do, your COM permissions or packages may need to be looked at to see if everything is ok. Most often, it is a custom app that is crashing the process.