Re-direct Chains - CMS Migration

[Rysk100]

I'm in the process of planning a migration of a site from a proprietary CMS to Wordpress

There are number of URLs on the current CMS with re-direct chains due to http > https
1) http:// bestwidgets.com/widget/green > 2) https:// bestwidgets.com/widget/green > 3) http:// bestwidgets.com/widget/green-large > 4) https:// bestwidgets.com/widget/green-large

i.e old slug > old slug on https > new slug on http > new slug on https

Most 301 plug-ins on WP only have 2 fields (old > new)

How / what should I do with these re-directs?
I'm thinking that I only need to re-direct old slug on https > new slug on https

[htmlbasictutor]

Why are you moving to Wordpress?

How long ago did you switch to https?

Google's John Mueller said in the Google+ Hangout from last Friday that he'd recommend you keep your 301 redirects live and in place for at least a year after you set them up. He said "I'd aim for at least a year," when it comes to keeping your 301 redirects in place.

He said it can take 6-months to a year for Google to fully recognize a site has moved. Plus you may have people finding old links and if those no longer have redirects, they may lead to a 404 page or a parked domain, which would result in a bad user experience.

Source: Google: Keep Your 301 Redirects Active For Over A Year
[seroundtable.com...]
Sep 14, 2015

You could download the htaccess file created by Wordpress and add your existing redirects to it.

Here is an article from Moz about redirect chains and SEO:
Here’s How to Keep 301 Redirects from Ruining Your SEO
[moz.com...]

Back in 2011 Matt Cutts did this video for Google Webmaster Central
Is there a limit to how many 301 (Permanent) redirects I can do on a site?
[youtube.com...]

[lucy24]

Most 301 plug-ins on WP

Do you want the good solution or the easy solution? The good solution, whether you're moving to, from or within WordPress--or any other CMS--is to code the redirects yourself.

http vs. https then becomes completely irrelevant, because your redirect code looks only at the request path, not the protocol or hostname, while the target always includes the correct https://example.com form.

You don't say what type of server you're on. Assuming Apache, you will need to make a set of RewriteRules and place them immediately before the RewriteRules that are specific to the CMS. Details will depend on how many URLs are involved, on what types of patterns you can find between old and new, and other variables that again depend entirely on your site.

Keep Your 301 Redirects Active For Over A Year

Hahahahaha. Keep your 301 redirects in place FOREVER. And that's all.

[not2easy]

There shouldn't be any https: rewrites other than the domain rewrite. The scenario described should only need to deal with /widget/green > /widget/green-large

The rewrite chain described means that http: is not rewriting to https: which would mean it could be accessed either way.

WordPress uses the permalink structure that you set up when you install it so you want to set up a structure that makes those rewrites easier. The new structure may or may not maintain your existing structure due to its inserting parameters such as /archives/, /categories/ and whatever /tags/ it finds.