I had this issue back in 0.9.9.4 but seemed to have been resolved after I updated to 0.9.9.6. Again I find that I cannot really work the media upload. The symptoms are odd. Upon creating a new post it will let me upload using the media modal native to WordPress. Then its locked out for the most part. When I try to remove and update the post – it remains. I can upload more without a problem and I can remove the second onward, but never the first one that I uploaded. I am pulling my hair (*what’s left of it) at this point.

This is the meta-box I setup:

 piklist('field', array(
    'type' => 'file'
    ,'field' => 'post_header_banner'
    ,'scope' => 'post_meta'
    ,'label' => __('Add File(s)','piklist')
    ,'description' => __('Upload Top Banner.','piklist')
    ,'options' => array(
      'modal_title' => __('Add Banner Image','piklist')
      ,'button' => __('Add Banner','piklist')
    )
    ,'validate' => array(
	  array(
	    'type' => 'limit',
	    'options' => array(
	      'min' => 0,
	      'max' => 2
	    )
	  )
	)
  ));
  
  
  	 piklist('field', array(
    'type' => 'file'
    ,'field' => 'post_title_banner'
    ,'scope' => 'post_meta'
    ,'label' => __('Add File(s)','piklist')
    ,'description' => __('Upload Title Banner.','piklist')
    ,'options' => array(
      'modal_title' => __('Add Title Image','piklist')
      ,'button' => __('Add Title','piklist')
    )
    
    ,'validate' => array(
	  array(
	    'type' => 'limit',
	    'options' => array(
	      'min' => 0,
	      'max' => 1
	    )
	  )
	)
    
  ));

If I go into the database I can see the postmeta section with the post_header_banner populated with the image ID of the first image. From here I can put in another ID and it updates nicely without a hitch.

I read through the forums and found that some people were experiencing similar issues with far more complex setups than what I am doing. I even added the limits to see if setting the min but no dice!

Then I figured it had something to do with not being explicit with setting capability on the meta-box file. Nope.

I turned off all the plugins to make sure they weren’t conflicting. Nothing.

I already went back in time to the previous releases, including the one still posted as the current release on WordPress Plugins section.