.htaccess redirect 301 doesn't work for all links

Question

Recently I've been having weird issues with one of my htaccess files. Basically, I had to Redirect 404 pages to relevant subpage, and I checked few random ones and thought everything was working fine until I checked all of them and realised only about 60% of my rules did work.

I was unable to find solution to my problem and I tried quite few approaches.

Here's list of Examples of the Redirect 301s that I'm using:

Redirect 301 /products/sampleproduct http://www.mysite.co.uk/products/overhead-lifting-solutions
**Redirect 301 /products/sampleproduct/rail-system http://www.mysite.co.uk/products/overhead-lifting-solutions/rail-systems
**Redirect 301 /products/sampleproduct/floor-wall-mounted-cranes http://www.mysite.co.uk/products/overhead-lifting-solutions/jib-cranes
**Redirect 301 /products/sampleproduct/vacuum-lifter-easyhand-t http://www.mysite.co.uk/products/overhead-lifting-solutions/vacuum-lifters
Redirect 301 /products/sampleproduct/vacuum-lifter-easyhand-m http://www.mysite.co.uk/products/overhead-lifting-solutions/vacuum-lifters
**Redirect 301 /products/sampleproduct/vacuum-lifter-vacuhand-v http://www.mysite.co.uk/products/overhead-lifting-solutions/vacuum-lifters
**Redirect 301 /products/sampleproduct/end-effectors http://www.mysite.co.uk/products/overhead-lifting-solutions/end-effectors
Redirect 301 /products/sampleproduct/mechline http://www.mysite.co.uk/products/overhead-lifting-solutions/chain-hoists
**Redirect 301 /products/sampleproduct/mechchain http://www.mysite.co.uk/products/overhead-lifting-solutions/chain-hoists

Redirects that don't work were marked with **. I have over 160 Redirect where about ~60 do not work.

Answer 1

2nd Redirect rule is not working because first one is taking precedence. First rule is redirecting anything starting with /products/sampleproduct thus overriding /products/sampleproduct/rail-system all the time. You can either reverse the order of rules or better use RedirectMatch with regex support like this using regex anchors:

RedirectMatch 301 ^/products/sampleproduct/?$ http://www.mysite.co.uk/products/overhead-lifting-solutions
RedirectMatch 301 ^/products/sampleproduct/rail-system/?$ http://www.mysite.co.uk/products/overhead-lifting-solutions/rail-systems

You need to make this fix for rest of your rules and make sure to clear the browser cache before testing these.