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Two version on Story - only one shows in timeline

I have some versions set for my Milestones, and they are filled in in my stories. Now I want to add some "small", checkpoint milestones, that basically split up a long milestone.

If I assign the checkpoint to the story, it says "two versions" on the story in my backlog (correctly), but only the first "version" on the story shows on the timeline.

I want the milestone to be like

Milestone 1 -----Checkpoint 1------Checkpoint 2-------Milestone 2-----....

The milestone 1 period goes  to the beginning of milestone 2. The checkpoints are a subset of the timeline for the enclosing Milestones. The checkpoints are not rendered on the timeline.....

Maybe I should rethink how I am going about this. Anyone have a good way to do this that works

Anyone ... ?

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