I have a webserver that I wish to retire, and I've already moved its content to a subfolder on another server. Can the root URL that I've been using for the first server point to the second server's subfolder? My understanding is that this cannot be done through CNAMEs in a DNS. If I set the DNS so that, say, second.mysite.com has the same IP address as www.mysite.com, can the server detect the incoming URL and automatically redirect to the subfolder?
Yes, in IIS. The configuration of your old site, you can set it to redirect to the new sub folder
What you're talking about is DNS records which can be accomplished on any server (not just IIS).
HOWEVER, since you can take a site down with a DNS error, I would rely (first) on mod_rewrite which can be setup to redirect to any web address whereas DNS will only redirect to another (registered) domain.
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