I have about a hundred URLs I need to map from old HTML site to new DNN site, and have been evaluating URL Master as a quick way to deal with changed page names, which include the year and month, and of course have gone from .htm to .aspx.

Old format:

http://www.example.org/letter/archive/2008-01.htm
http://www.example.org/letter/archive/2006-02.htm

http://www.example.org/newsletter/2008/January2008.aspx
http://www.example.org/newsletter/2006/February2006.aspx

Other than the painful one-page-at-a-time mapping to the new pages, is there a way to accomplish this with URL master using RegEx or wildcards, etc.??

Since each newsletter monthly issue is a separate DNN page, I guess you're saying that each of theses page would require a row in the redirection table, correct?  In other words, each redirection happens based on an actual entry in a redirection table, not based on some type of dynamic mapping rule....?

Yes, there are no 'catch all' rules for redirects in the module at this stage.  If you've got a one-to-one mapping of the newsletter to DNN pages, then you'll need to create a new DNN page for each newsletter, and add a redirection for each of those pages.  

You can do this quickly yourself by creating a sql statement to insert into the ifty_TabRedirect table, or you can do it through the interface.

The colums you need to set are TabId, RedirectTabId - the same as the page you want to redirect to.  Url - the path section of the redirection you'd like to capture (ie newsletter/jan-08 or whatever the url you would like to intercept was.  The httpStatus column should read '301'.

The IIS settings are mapping .htm to the asp.net runtime  - you don't need to wildcard the extension if you don't need to, just map .htm and you'll be able to redirect.