Hi @Nichol Pope , and welcome to the Atlassian Community Forums!
I believe your question relates to Jira Work Management, and, unfortunately, there is not any default capability for this.
Two thoughts here. One would be to add a few custom fields (one for original due date, and one for the modified due date). You could then create alerts/notifications based on those fields. However, this doesn't, by default, do anything with the timeline so doesn't really help you with what you need.
The second is to look into some of the marketplace options that relate to the "timelime" for Jira Work Management. Many of the apps have free trials, or you can contact the vendor to ask whether their app provides the functionality you are needing.
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