Weird issue with Milestone rule

I have created a rule that checks when 2 specific CTA’s have been closed. There are 2 actions in the rule both create milestones of the same type but for different reasons. For some reason the first action works fine, it creates the timeline entry and also appears in the customer journey widget. The second action also appears to work and can be observed to work in the execution logs, however no timeline entry is created and it does not appear on the customer journey widget either. Has anyone else had this problem? Any advice would be appreciated!