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I like this suggestion, @codinghorror’s call on the wording here. I agree calling italics emphasised in the tooltip is somewhat confusing. Looking at Stack Exchange sites it uses “Emphasis” and “Strong” so there is precedent even in non tech sites. GitHub uses “Bold” and “Italic”.

Regarding making Italics/Bold smarter. There are quite a few edge cases… for example, when you highlight this block and hit “B” what do you expect?

- test
    -  text
-test
(3) test

4. test

[spoiler]
test
[/spoiler]

test [i]test
test[/i]

The ideal outcome has a LOT of magic rules, and we don’t want to have to write a full parser here.

- **test**
    -  **text**
**-test**
**(3) test**

4. **test**

[spoiler]
**test**
[/spoiler]

**test [i]test
test
[/i]**

I am sort of pr-welcome here, but we got to determine what a very simple set of rules that capture the 99% case first.

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