Under some pressure to change the permalink structure of a fairly active 15+ year old news site

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Hi all, needless to say I have some concerns about this but the boss in this situation isn’t budging, so I thought I’d ask if anyone has any experience with this kind of situation.

We’re currently using a simple url.com/post-name structure, and the intent is to move to a url.com/cat-name/post-name structure. The move itself makes sense, but obviously I have some reservations when it comes to broken links/SEO.

My plan is to use a 301 redirect plugin to basically redirect /%post-name%/ to /%category-name%/%post-name%/ since the plugin allows that sort of syntax when setting up parameters. I’m a little nervous to flip any switches here for obvious reasons (we’re talking about many thousands of articles), so I just thought I’d check in here first…basically see if anyone’s navigated a similar situation, or if my proposed plan is a disaster in the making, etc.

Any help or insight is much appreciated!

Edit: I should mention that the reason for this move is purely for GA4 analytics tracking by category.

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