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With some help (also asked on SO, as this wasn't a strict WP question), and some testing, the following ended up working for me (added a slash just before the $ sign): RewriteRule ^galleries/(.*)/$ /portfolio/$1 [R=301,NC,L] As the galleries are actual directories, not files, they have a slash at the end: http://subdomain.example.com/galleries/headshots/ ...

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