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When I'm writing a plugin, do I assume that jquery is included, or should I always wp_enqueue_script it and let wordpress figure it out?

Also, what's the best practice for getting an image path figured out in my bundled css file?

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One point for using wp_enqueue_script is for that very reason. Never assume anything, enqueue jQuery so that if it is there already it does nothing, but if not , it will queue it up.

If your talking about the image path for your plugin, you can use the following, http://codex.wordpress.org/Determining_Plugin_and_Content_Directories

The examples for plugins_url should help.

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