"Page isn't redirecting properly" message

Can you give some examples of short vs long urls ? and do you use the regex feature or not ?

Rules are applied in the order they are listed and can cause loops.

Yes, an example of a long URL would be https://www.outstandingpresentationsworkshop.com/this-is-a-page-with-a-long-title. A short URL would be https://www.outstandingpresentationsworkshop.com/short/
At the time, I had only 1 redirect.
I don’t know what the regex feature is.

Why not just use the Shortlinking built into WordPress? By default, the shortened URL is simply domain.com/?=123 (where “123” is the Post ID).

If you have the WordPress.com Stats/JetPack Plugin installed, you get the wp.me URL shortener as part of the Plugin, that hooks into the core shortlink functionality.

Or, you can use one of the several bit.ly Plugins that hook into the core shortlink functionality.

And then there’s always the YOURLS plugin, to roll your own URL shortener.

If that is the only redirection you had, the redirection plugin shouldn’t be causing the looping…

Can you look at the server logs to see the redirection path the page is taking ? That should give you some clues on how and why this is happening.