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I am getting an 'HTTP Error' when uploading images to posts. What could be the reason for this? It doesn't happen all the time, sometimes I get the error, try again, and the file uploads. Actually the file always seems to upload, however it doesn't generate the different sized images or anything.

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There a couple of different solutions depending on the cause of the problem.

In your case it seems that is not a upload problem. I would rather try adding the following plugin

Plugin Name: Default to GD
Plugin URI: http://wordpress.org/extend/plugins/default-to-gd
Description: Sets GD as default WP_Image_Editor class.
Author: Mike Schroder
Version: 1.0
Author URI: http://www.getsource.net/

function ms_image_editor_default_to_gd( $editors ) {
    $gd_editor = 'WP_Image_Editor_GD';

    $editors = array_diff( $editors, array( $gd_editor ) );
    array_unshift( $editors, $gd_editor );

    return $editors;
add_filter( 'wp_image_editors', 'ms_image_editor_default_to_gd' );

This will change the default image editor

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