Firstly, this is a question relating to Outlook not Tumblr although I'll explain where Tumblr comes into this throughout this question. Also to clear any misunderstanding of the thread title, this isn't about copying/drag/dropping pictures from the Tumblr website into Outlook. SO, here goes. I have 20 pictures in a Folder called '2Publish' (a Folder '2Publish' within the 'My Pictures' Folder on my PC). I press CTRL+A to select all the pictures in the '2Publish' Folder, I then hold down the left button on the mouse and drag/drop the selection directly into a Folder within Outlook called 'Tumblr'. So far so good, this works. Note here: although all the pictures are now in the 'Tumblr' Folder within Outlook, they are not messages/emails; they are .JPG files within the 'Tumblr' Folder. The next thing I do is to Categorize all the drag/dropped pictures with a green flag. I then have a rule I run that forwards all 20 pictures (from the Outlook default email account) and that are green flagged to my Tumblr Publishing Blog email address. So far, this works. Outlook send all 20 pictures individually (not as a single email with 20 attachments). But .. this is where something goes wrong. When I now check my Tumblr Blog, none of the pictures have been published. I have tried both the 'Forwarding' AND 'Forwarding as an Attachment' option within the rules; still, this doesn't work. What does work (and isn't the way I want) is the long manual way to get all the 20 pictures published on my Blog only if I sit there and manually create 20 new email messages attaching each picture to each email. Any ideas why manually sending emails individually works yet having Outlook do it all but running a rule doesn't work?