Is there a way to post a link with a dynamic image to Twitter?

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This may not be the best place to ask, but I've tried multiple other resources, and my searches have led me here.

I am trying to create a link that, once posted to Twitter (or another site) randomly generates an image from a specific list of images saved to my computer (or uploaded to the site). The tool would produce a new random image upon the page being refreshed.

I know that this is possible for other sites, because back in the day (2009ish), I used an online tool to generate a random banner for my guild on GaiaOnline. The site that I used (undev dot org, with the help of Tinypic) no longer exists, and I cannot, for the life of me, find something similar. It probably exists, but I can't figure out what to google to find it.

Someone recently suggested I search for a "dynamic header" for Twitter, but it's not a header that I want. I want to be able to put the link in a post on Twitter, and then every time that the post is refreshed, a different image appears in the post.

Does anyone know of a site that will allow me to accomplish this? Is there something else I should try searching google for? If not, is there another way that I can achieve this goal? I'm new to programming (C++ and a little bit of Python), and I'm not sure what else I would need to learn or learn about in order to achieve this. Thank you.

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What you are looking for is Twitter Cards (the snippets that appear on Twitter when you paste a link), however, they are cached for 7 days so there is no way to do this with dynamically updating images.