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It's not that hard to make a plugin to TinyMCE, similar to what the Wordpress gallery is doing in WP 3.5. Unfortunately, these custom placeholders are always non-resizable, although they show the resizer handles.

A new image inserted into a post is resizable with the handles, an embedded iframe is resizable, but a new gallery placeholder is not resizable (in this case it doesn't make sense, galleries don't resize). However, I need a custom placeholder that is resizable. Is there a special class that turns this on or off, or a function that I need to call to enable resizing on a certain element?

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Looks like removing the height: and width: from the css makes it resizable :)

I had copied css with those settings.

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