Hi @hagstrom
You can do that in MS Word too since the product was released in the 90s.
1. Add a tab to the ruler by clicking onto the ruler at a desired position.
2. Double click onto the tab to see the Tabs option.
3. Under Leader, click onto option 2.
4. Click Set.
5. Press the Tab key and the cursor will move to the new tab. You'll see a leading line appear.

Alternatively, you appear to be doing the TOC manually. You could use Headings 1, 2, 3, etc and have the Table of Contents automatically generate by going into the References tab > Table of Contents. This table will update when you right click onto it and updates any changes to headings and page numbers.
Best wishes!
Damien