The Aaron said: Because of the way that images are supported as a special case url link, it only looks for .jpg and .png files. You can get around that issue (and the issue of URLs that don't end in image extensions) by appending a URL Fragment to clue in the parser to it being an image: [ignoretext](URL.gif #.png ) Appending #.png to the URL will let the parser understand that it should treat that link as an image. Thank you so much! This worked very well. ∇ince said: Dakota H. said: I have never had to do that. I use *.gif links all the time in Roll20. It could be that the template the OP is using doesn't support an image output. Some url's to image links might look like; <a href="https://s3.amazonaws.com/files.d20.io/images/106406303/B6jOZ1zkWBahi5KQ-up44A/thumb.jpg?1583176727455" rel="nofollow">https://s3.amazonaws.com/files.d20.io/images/106406303/B6jOZ1zkWBahi5KQ-up44A/thumb.jpg?1583176727455</a> notice that it's an image, but it doesn't end with an image extension (.jpg, .png, .gif, etc.) You could either remove those extra characters after ".jpg 1583176727455 " or you can use Aaron's trick and simply append ".png" on the end of it. Here's a handy macro that will do this auto-magically if you want to easily post to an image to chat. [Image](?{URL}#.png) Sorry but this didn't work out~