Round-tripping issue

Since becoming a Creative Cloud subscriber I haven't had to do this but what I did do in the past was as follows:

1. Double click on the image file from the library to open the Image Properties 
2.  Click the Edit... button to open the image in the image editor of your choice.
3. Rather than closing the image and hoping it will load up in Captivate I would save the edited image to my desktop and close the image editor.
4. return to Captivate where the Image Properties window is likely still open and click on the Import button. This will allow you to navigate to where you saved the item and import the new version with all your changes.

Yes, it's an extra step but it saves you having to make multiple attempts and multiple edits. I'm fairly certain that whatever coding is required to make this work in Captivate is optimized for software like Photoshop or Audition for audio and so on. Hope that helps.