WordPress does not redirect automatically. You could use the Permalink Redirect Plugin
http://scott.yang.id.au/code/permalink-redirect/
Thanks for the reply! Is there a certain amount of time that would need to pass to be able to remove the plugin? Or would it always be needed?
It would be needed until all of the old links on various search engines or websites have been removed. So basically yeah it will be always needed.
Why remove it anyway? It’ll help in the future.
While u have a URL with old permalink in any site, u will still need the plugin
But why do u want to change from /postname/ to /year/month/postname?
I suppose u’ve already changed permalink before.
I suggest that u install a testing blog and test all possible links, being posts, pages, dates, categories, etc, and if they are being redirected correctly, before u try to do it on ur main blog.
I guess I just like to have as few plugins as possible. Thanks for the reply, I really appreciate it!
Is it ok to use /%postname%/, despite what it says on the WordPress website?
Using only %postname%
If you use postname as the only element in your permalinks to create a structure such as example.com/post-title, the rewrite rules may make it impossible to access pages such as your stylesheet (which has a similar format) or the /wp-admin/ folder [is this true in WordPress 2.0+ versions?]. It’s best to include some numeric data (e.g. the post ID or date) in the permalink to prevent this from happening. Additionally, WordPress v1.2.x requires the use of a date structure in order for some features, such as the calendar, to function properly. /%year%/%monthnum%/%day%/%postname%/ is always a good start.
From what I’ve read you can do it, but you need to be very careful with naming your posts so that they don’t create a database conflict with files in the wp-admin folder. To me that sounds like you need to be sure that you know all the names of those wp-admin files so that you don’t muck it up.