If a new post contains both an image either "Linked To Image" or "Linked To Page" and an apostrophe anywhere in the post (') then the apostrophe is not escaped properly causing a database error.
Here's the HTML code version of a post:
<p>' <a title="Tim & Tom Just Arrived" onclick="doPopup(7);return false;" class="imagelink" rel="attachment" id="p7" href="http://www.dave-miller.com//?attachment_id=7"><img width="120" height="96" alt="Tim & Tom Just Arrived" id="image7" src="http://www.dave-miller.com/wp-uploads/2006/02/Photo-0335.thumbnail.jpg" /></a></p>
And the error when I clicked Save & Continue Editing - notice the ' is not escaped in post_content:
WordPress database error: [You have an error in your SQL syntax. Check the manual that corresponds to your MySQL server version for the right syntax to use near 'title="Tim & Tom Just Arrived" class="imagelink" rel="attachmen]
UPDATE IGNORE wp_posts SET
post_author = '1',
post_date = '0000-00-00 00:00:00',
post_date_gmt = '0000-00-00 00:00:00',
post_content = '' <a title="Tim & Tom Just Arrived" class="imagelink" rel="attachment" id="p7" onclick="doPopup(7);return false;" href="http://www.dave-miller.com/?attachment_id=7"><img width="120" height="96" alt="Tim & Tom Just Arrived" id="image7" src="http://www.dave-miller.com/wp-uploads/2006/02/Photo-0335.thumbnail.jpg" /></a>',
post_content_filtered = '',
post_title = 'Test',
post_excerpt = '',
post_status = 'draft',
comment_status = 'open',
ping_status = 'open',
post_password = '',
post_name = '',
to_ping = '',
pinged = '',
post_modified = '2006-02-12 19:14:38',
post_modified_gmt = '2006-02-12 19:14:38',
post_parent = '0',
menu_order = '0'
WHERE ID = 15
Warning: Cannot modify header information - headers already sent by (output started at /home/.../wp-includes/wp-db.php:102) in /home/.../wp-admin/post.php on line 122