One of the more bizarre changes that happened to Lightroom when the Import module was changed was the operation of the 'Into Subfolder' option. Why? Well when you try to use the Subfolder option with an date option, the Subfolder is actually a Parent Folder for a dated folder. Em? WTF? Yep, it makes no sense to me either.
I have been a fan of using a strict dated system for managing folders. It's a great way of making sure there's an organisation structure in place. As time is going by, I'm starting to wish I had names to go with those dates. Maybe it's old age catching up on me.. ok, I'm not that old.
So, how to overcome this with ease? Well, we can make use of another annoying trait of Lightroom Import to solve this issue. When you start importing, Lightroom creates a folder in the Catalog Panel called 'Current Import'. As soon as Import finishes copying files, it becomes the 'Previous Import' folder.
First let's go with a simpler Date Option. In this case I choose 2012/09. I want my subfolder in a month folder rather than inside a date-it's just too deep in the hierarchy then.
Select all the files in Previous Import.
Right click on any photo and choose 'Go to Folder in Library'. This goes to the Month folder, with our images still selected-we don't want to select other images that may already be in this folder, which is why we did the selecting in Previous Import.
Now go to the Folder panel header and click the + and choose 'Add Subfolder'.
This opens the Create Folder Dialog, with 'Put Inside 09' already selected. Tick the 'Include selected photos' box, and give your folder an appropriate name. Click 'Create'. This makes a folder called Katherine inside '09', our month folder.
The actual process is far quicker than this. You could also use the 'Into One Folder' option and manually create the parent folders as you need, but this way the dated folders are created automatically, and you're taken to the correct month folder each time. Personally I wish the Into Subfolder option did actually make a subfolder, but that's a design choice on behalf of the Lightroom team.