Change permalinks on move from one site to another

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I don’t know how the IIS rewrites will impact things, but outside of that, I would recommend:

  1. Use Dashboard -> Tools -> Export to export your site content from the .com site
  2. Setup the identical permalink structure on the .org site
  3. Use `Dashboard -> Tools -> Import to **import your site content to the .org site
  4. Then change your permalink structure

This way, you can take advantage of the built-in WordPress permalink redirection functionality.

By setting up the .org site permalink structure identically to the .com site permalink structure, when you import the content, the permalinks will initially be set up identically. That (should) allow your .com redirect plugin to redirect correctly.

Then, when you change your permalink structure on the .org site, WordPress will apply metadata in order to redirect properly from the old permalink structure to the new permalink structure. That way, the process should work like so:

  1. User requests old permalink from .com site
  2. The .com site redirects to the old permalink at the .org site
  3. The .org site receives the request for the old permalink, and serves the correct, new permalink