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You can try making a post with this in the markdown box:
**Table of Contents**

{:toc}

# Heading 1

Some text.

## Heading 1.1

Some more text.

# Heading 2

Even more text.
Try it out and see how it looks (make modifications as desired)
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Cool. Why can't we use it on comments?
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Heh, there was some internal discussion about whether it should be enabled for comments too. Can read about it here: https://github.com/stackernews/stacker.news/pull/2213
Short answer is probably just that we don't think any would really need to use it for comments.
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