Outlook signature has lost images when I edited it in word

Hi there I have a number of HTML signatures set up on a server which gets downloaded to the users PC when they logon. The MD decided that he would like to change some of the wording on his and edited the signature through outlook using Word as the editor. Now when he opens a new mail he has lost a number of images. It just shows the place holder.

It is fine if we switch to using word as our e-mail editor but we dont use word as our e-mail editor as a general rule

It seems that once you edit the signature with word it causes the problem. Is there any way to correct this problem.