Moving large static website with thousands of pages to WordPress, how to handle 301’s?

I am in a situation where I have a static website that has been in existence for over 8 years and has thousands of pages of content.

I need to move this site to WordPress and have found a plugin that does a great job of handling most of the legwork for me, but the question is how to handle all the redirects?

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Correct me if I am wrong, but wont cluttering up an .htaccess file with thousands of redirects affect page load time?

Another caveat to this is that the domain name isn’t changing, and there are thousands of horribly named .shtml files that will be re-named using WordPress Perma-links. The plug-in we’re using to ingest the static pages into WP provides a list of redirects, but it just seems like there has to be a better way than adding thousands of lines to an .htaccess file to accomplish this.

So, my question is, what is the best practice for performing such a task, and, is there a programmatic way to handle it?

Thanks in advance!

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  1. If the names are matched – meaning that www.example.com/my-page.shtml is being made www.example.com/my-page – and this is 100% consistent – then you can create a redirect rule that just removes the .shtml: stackoverflow.com/a/11335332/870729:

    RewriteCond %{THE_REQUEST} .shtml
    RewriteRule ^(.*).shtml$ /$1 [R=301,L]
    

    Also, IMO, using htaccess will be FAR faster / more efficient than using a php / programmatic method to redirect. This style of redirect rule should have no noticeable impact on performance / load times.

    Lastly, again IMO, it would be wise to make the “shtml” redirect first, let it sit (Google should pick it up in a few weeks, especially if you create a sitemap and submit to Google Webmaster Tools). Then you can begin the process of renaming the page(s) to more SEO-friendly / human-readable titles as it makes sense.