HI @cwibben 
Welcome to the Community!
If you’d like to see your timeline reflect the status of each item, you can select this from the settings in the Timeline view, rather than through the Deadline Mode feature.
When setting up your Timeline you will be able to select which logic should be used to colour the timeline bars in the ‘Color by’ drop down:
Selecting the Status will then allow you to visually see the status of all the items in the view!
I hope this helps! Remember to mark as solved if this answers your question 
Best,
Dani