I am occasionally asked if Simple 301 Redirects will allow you to redirect your old blog on WordPress.com to your new self-hosted blog installed from WordPress.org. It won’t but there’s an easy way to do just that.
Simple 301 Redirects only works if you can install it on the site you’re redirecting from. Since you’re redirecting from a WordPress.com blog you won’t be able to install my plugin there. What you can do instead is utilize a premium upgrade offered by WordPress.com called Site Redirect, accessible from the WordPress.com dashboard.
As of January 2014 it costs $13 a year. What it does is redirect all of the URLs from your WordPress.com blog to the same URL at a domain of your choosing. It is, in essence, a domain-level redirect.
How long should you pay for it?
Determining how long to keep your Domain Redirect in place depends on where your traffic comes from. You should be OK to cancel it after a year or two if most of your traffic comes from search engines. Search engines will see the 301 redirect and update their indexes.
If most of your traffic comes from inbound links on other sites you may want to keep the redirect in place indefinitely so those links continue working forever.