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In our plugin we calculate the ContentType based on metadata. Since metadata may change without changing the file pointing to the metadata, the contenttype is never recalculated. There is a public method "invalidateCache" but no way to reach it. It seems like there is no support for a ContentDescription/ContentType Change Notification.
Renaming as a feature request as this is not exactly a bug. In general, it seems to me that what you're doing is wrong regarding the concept of a content-type. A content-type should be only related to file name and file content. If you need some other things to sort out a content-type, then it means what you're dealing with isn't really a content-type but another concept which is specific of yours. Let's keep this bug open for some time, but given that the user-story behind it seems to not be a "clean" one, we'll probably end up marking this one as WONTFIX.