Edit Hyperlink dialog box of an image inside a Windows Live Writer  post. Check box is off by default on all pasted [inserted] images.
I just had an odd but old, familiar occurrence. The image on my blog post on my WordPress blog failed to load. There was just a solid gray box in it’s place with an X, if I recall correctly, in the upper left corner of the image placeholder in the webpage.
Since I just posted the first original version of that particular blog post I remembered one thing I did differently. I right-clicked on the image, clicked the Hyperlink… command:
Then checked Open link in new window:
Clear the check box Open link in new window for that particular image in the Edit Hyperlink dialog box and click Publish to update the version on the WordPress [blogging] server.