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Hi GracieAllen

I too could not get the Delete and Fill contextual menu option to record in Actions either.

You might want to post that in the Adobe Community Forum as a bug or feature request.

It very well may be beyond what you want to do is to do this by a script.  A common approach is to record the steps with the Scriptlistener Plugin.  If you want to get a feel for what is involved here is a link: https://helpx.adobe.com/photoshop/kb/downloadable-plugins-and-content.html

There is some work to strip out exactly what you want to include in what was recorded

Then you can call that script via File > Script > Browse to where you save the script or you can call the script through an Action as well

It is quite a bit of work to take this path yet I bet it would work

John Wheeler