diff -up ./lightbox2-insert-image.tpl.php.insertstyles ./lightbox2-insert-image.tpl.php
--- ./lightbox2-insert-image.tpl.php.insertstyles	2010-02-11 23:12:22.000000000 +0000
+++ ./lightbox2-insert-image.tpl.php	2010-02-11 23:12:22.000000000 +0000
@@ -0,0 +1,26 @@
+<?php
+// $Id$
+
+/**
+ * @file
+ * Template file for Lightbox2 content inserted via the Insert module.
+ *
+ * Available variables:
+ * - $item: The complete item being inserted.
+ * - $url: The URL to the image.
+ * - $linkurl: The URL to the image being linked to.
+ * - $class: A set of classes assigned to this image (if any).
+ * - $image_preset_name: The ImageCache preset being used for the image.
+ * - $link_preset_name: The ImageCache preset being used for the linked to image.
+ *
+ * Note that ALT and Title fields should not be filled in here, instead they
+ * should use placeholders that will be updated through JavaScript when the
+ * image is inserted.
+ *
+ * Available placeholders:
+ * - __alt__: The ALT text, intended for use in the <img> tag.
+ * - __title__: The Title text, intended for use in the <img> tag.
+ * - __description__: A description of the image, sometimes used as a caption.
+ */
+?>
+<a rel="lightbox[group1][__description__]" href="<?php print $linkurl ?>"><img src="<?php print $url ?>" alt="__alt__" title="__title__" class="imagecache-<?php print $image_preset_name ?><?php print $class ? ' ' . $class : '' ?>" /></a>
\ No newline at end of file
diff -up ./lightbox2.insert.inc.insertstyles ./lightbox2.insert.inc
--- ./lightbox2.insert.inc.insertstyles	2010-02-11 23:12:22.000000000 +0000
+++ ./lightbox2.insert.inc	2010-02-11 23:12:22.000000000 +0000
@@ -0,0 +1,127 @@
+<?php
+// $Id$
+
+/**
+ * @file
+ * Lightbox2 support for Insert module.
+ */
+
+/**
+ * Implementation of hook_insert_styles().
+ */
+function lightbox2_insert_styles() {
+  $insert_styles = array();
+
+  $insert_styles['lightbox2--original--original'] = array(
+    'label' => 'Lightbox2: original->original',
+  );
+
+  // Handle imagecache presets.
+  if (module_exists('imagecache')) {
+    $rules = array();
+    if (function_exists('imagecache_presets')) {
+      $presets = imagecache_presets();
+      foreach ($presets as $preset_id => $preset_info) {
+        $rules[$preset_id] = $preset_info['presetname'];
+      }
+    }
+    else {
+      $rules = _imagecache_get_presets();
+    }
+    /*
+    $insert_styles['lightframe2--original--node'] = array(
+      'label' => 'Lightbox2 iframe: original->node page',
+    );
+    */
+    foreach ($rules as $ruleid => $view_rule) {
+      $insert_styles['lightbox2--original--'. $view_rule] = array(
+        'label' => 'Lightbox2: original->'. $view_rule,
+      );
+      $insert_styles['lightbox2--'. $view_rule .'--original'] = array(
+        'label' => 'Lightbox2: '. $view_rule .'->original',
+      );
+      /*
+      $insert_styles['lightshow2--original--'. $view_rule] = array(
+        'label' => 'Lightbox2 slideshow: original->'. $view_rule,
+      );
+      $insert_styles['lightshow2--'. $view_rule .'--original'] = array(
+        'label' => 'Lightbox2 slideshow: '. $view_rule .'->original',
+      );
+      $insert_styles['lightframe2--'. $view_rule .'--node'] = array(
+        'label' => 'Lightbox2 iframe: '. $view_rule .'->node page',
+      );
+      */
+      foreach ($rules as $rid => $lightbox_rule) {
+        $insert_styles['lightbox2--'. $view_rule .'--'. $lightbox_rule] = array(
+          'label' => 'Lightbox2: '. $view_rule .'->'. $lightbox_rule,
+        );
+	/*
+        $insert_styles['lightshow2--'. $view_rule .'--'. $lightbox_rule] = array(
+          'label' => 'Lightbox2 slideshow: '. $view_rule .'->'. $lightbox_rule,
+        );
+	*/
+      }
+    }
+  }
+  /*
+  if (module_exists('emfield') && module_exists('emimage')) {
+    $insert_styles['emimage_lightbox2'] = array(
+      'label' => t('Lightbox2: Image Thumbnail -> Original'),
+    );
+    $insert_styles['emimage_lightshow2'] = array(
+      'label' => t('Lightbox2 slideshow: Image Thumbnail -> Original'),
+    );
+    $insert_styles['emimage_lightframe2'] = array(
+      'label' => t('Lightbox2 iframe: Image Thumbnail -> Content'),
+    );
+  }
+  if (variable_get('lightbox2_enable_video', FALSE) && module_exists('emfield') && module_exists('emvideo')) {
+    $insert_styles['emvideo_lightvideo'] = array(
+      'label' => t('Lightbox2: Image Thumbnail -> Full Size Video'),
+    );
+  }
+  if (module_exists('filefield')) {
+    $insert_styles['filefield_lightframe'] = array(
+      'label' => t('Lightbox2 iframe'),
+    );
+  }
+  */
+  return $insert_styles;
+}
+
+/**
+ * Implementation of hook_insert_content().
+ */
+function lightbox2_insert_content($item, $style, $widget) {
+  if (preg_match('/^lightbox2--((?:-(?!-)|[^-])+)--((?:-(?!-)|[^-])+)$/',$style['name'],$matches)) {
+    $image_preset_name = $matches[1];
+    $link_preset_name = $matches[2];
+    return theme('lightbox2_insert_image', $item, $widget, 'view', $image_preset_name, $link_preset_name);
+  }
+  else {
+    return '';
+  }
+}
+
+/**
+ * Theme the content that will be inserted for Lightbox2 presets.
+ */
+function template_preprocess_lightbox2_insert_image(&$vars) {
+  if ($vars['image_preset_name']!='original') {
+    $filepath = imagecache_create_path($vars['image_preset_name'], $vars['item']['filepath']);
+  }
+  else {
+    $filepath = $vars['item']['filepath'];
+  }
+  $vars['url'] = insert_create_url($filepath);
+
+  if ($vars['link_preset_name']!='original') {
+    $linkpath = imagecache_create_path($vars['link_preset_name'], $vars['item']['filepath']);
+  }
+  else {
+    $linkpath = $vars['item']['filepath'];
+  }
+  $vars['linkurl'] = insert_create_url($linkpath);
+
+  $vars['class'] = !empty($vars['widget']['insert_class']) ? $vars['widget']['insert_class'] : '';
+}
diff -up ./lightbox2.module.insertstyles ./lightbox2.module
--- ./lightbox2.module.insertstyles	2010-02-11 23:12:22.000000000 +0000
+++ ./lightbox2.module	2010-02-17 20:35:21.000000000 +0000
@@ -242,6 +242,11 @@ function lightbox2_menu() {
  * Implementation of hook_init().
  */
 function lightbox2_init() {
+  // Insert support
+  if (module_exists('insert')) {
+    module_load_include('inc', 'lightbox2', 'lightbox2.insert');
+  }
+
   if (lightbox2_exclude_these_paths() != 1) {
     lightbox2_add_files();
   }
@@ -895,6 +900,15 @@ function lightbox2_theme() {
     }
   }
 
+  // Additional Insert theme functions.
+  if (module_exists('insert')) {
+    // Theme functions in lightbox2.insert.inc.
+    $theme['lightbox2_insert_image'] = array(
+      'arguments' => array('item' => NULL, 'widget' => NULL, 'type' => NULL, 'image_preset_name' => NULL, 'link_preset_name' => NULL),
+      'template' => 'lightbox2-insert-image',
+    );
+  }
+
   return $theme;
 }