I use the Snipping Tool to simply paste the image into the text area of the discussion and it not only adds it in the text portion but it also automatically creates a file attached to that discussion.
Adding images to a discussion post
Ever felt the need to add an image to a post but did not wish to bother with uploading a new file into Clarizen?
Good news, now you can!
Discussion posts can now include images using a simple "copy paste", simply find the image you wish to add to the post copy it into your clipboard and then paste it inline into the post.
How to Copy/Paste:
Locate image file, mouse right-click + select 'copy image'
Click into the social discussion, mouse right-click + select 'paste'
Note: You can also use Ctrl + C and Ctrl + P to copy/paste files into social posts in place of the mouse clicks.
How to change the name of the file once pasted into the post:
Mouse-over (aka 'hover') over the file link
Click the file name to open up the in-line edit function - it should look like this: http://screencast.com/t/5diAcOxvy
Make your changes
Click outside of the bubble or ENTER to save your changes
Note: You can only change the filename with these steps prior to clicking POST.
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In order for the POST to be enabled, you will need to make sure the your System Settings 6.7 has "Allow All" selected.