Update all content types - Changes "Create a new..." to "Upload a new..."

One very strange piece of behaviour which I have been able to reproduce on two separate SP envrionments. One being Office 365 and  the other is our developer VM.

Using Visual Studio we deployed a solution for all site collections for content types. But we have some content types that needed to modified at the SC level and then push the changes down to the sites that leverage them.

1. The content type is not read only.
2. Force the DIP for the content type to always display
3. Advanced settings > Update all content types inheriting from this type > Yes > Ok

Now when I go to the library using that content type, the dropdown changes from "Create a new ..." to "Upload a new ..." which displays the Upload Document window. Completely different functionality than what is desired.

It occurs on the Office 365 environment so not a whole lot I can do concerning troubleshooting it there. But testing it on a VM has the same result. After a bit of Googling I found 1 other user state they had the same issue.

http://www.sharepointanalysthq.com/2010/06/content-type-publishing-in-sharepoint-2010/#_methods=onPlusOne%2C_ready%2C_close%2C_open%2C_resizeMe%2C_renderstart%2Concircled%2Constartinteraction%2Conendinteraction&id=I0_1357747702901&parent=http%3A%2F%2Fwww.sharepointanalysthq.com

Barry in the comments section, but no way to contact him.

Any help is greatly appreciated.