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I will also most likely be using an ISAPI Rewrite to fix the URLS for my dynamic pages. Would it be easier just to do everything in the Rewrite, or just fix the URLs with the Rewrite and stick with the 301 redirects from the old URLs to the new URLs?
Go to the IIS Manger.
Under the Web Sitres folder, right click on your site and select properties.
Click on the "Home Directory" tab
Press the "configuration" button
Edit the cfm application extension and select edit
In the Executable textbox, type in the full path to your aspnet_isapi.dll
(eg. C:\WINDOWS\Microsoft.NET\Framework\v1.1.4322\aspnet_isapi.dll)
Then Press OK
Now all your .cfm files will operate in the same way as .aspx files (they will run under the .NET framework).
Mapping file extensions through your desired application executable is just a band-aid, IMO. Do it the correct way the first time.
I refer you to Tim Berners-Lee's article:
Cool URIs don't change [w3.org]
I agree that 301s used to work really well. However have you tried them in Google lately. I've noticed a distinct change in how Google handle's 301s since a few months ago.
I've tried 301s with a number of sites recently and they have not recovered in Google to the same extent that they used to. This is a recent change.
The ideal situation is not to change your URI at all. A 301 should only be used as a last resort if you can not possible keep the URI the same.
Luckily, with IIS, there's no need to change it.
Bob-
I suggest you do some research on the hundreds of other posts regarding your topic within WebmasterWorld that ask the same question. You'll see a lot better responses from people that actually know what they are talking about.