Confused by 301 redirects not working

I used to have my entire website inside a folder on my website (/blog), and some of the site designed old-school. I recently moved the whole site over to WordPress, with the blogs homepage as /blogs/, though most of the time this is optional. Search results work with or without using /blog/ but they look better with as they’ll be titled “Blogs” and not “Search Results…”

Anyway, I use 301 Redirect plugin to change any of the old links from /blog/ to /blogs/ but some don’t do anything.

For example, I’ve set the redirect /blog/category/weddings/ to /blogs/category/weddings/
And it doesn’t redirect. When I click on the target URL it loads, when I click the old url it loads a not found. Yet the redirect is clearly listed.

Does it take a while to come into effect?

will a simple redirect of /blog/ to /blogs/ also redirect longer addresses with slugs that come after the folder name? Like /blogs/* Or do I have to set a redirect for every slug I want?