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It is stated in the stackoverflow FAQ:

*italic* or _italic_
**bold** or __bold__

so when I type three * followed by a word followed by another three * I expect to see the word to appear to be both italic and bold. Now this is work correctly.

Today I was formatting some message in a chat, I accidentally typed in this:

*this = ***that***

It appeared to read "this = *that" (with 'that' appeared to be bold & italic).

Is this not a bug?

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No, that is not a bug.

It is interpreted as such:

*                *
 this = *

so the outer stars surround this = ***that** making the whole text italic, bolding that, leaving the one extra asterisk hanging. The text is ambiguous at best; other markdown interpreters may leave the first asterisk hanging instead, like the parser used for posting questions and answers:

*this = that

clearly interpreted as

*this =           
       *        *

The Markdown standard doesn't specify how such ambiguous mixing should be handled, both interpretations are equally valid.

If you expected a specific interpretation, use \* to remove a given asterisk from consideration and use HTML tags (<em> for italics, <strong> for bolding) for the emphasis as needed:

*this = \*<strong>that</strong>*

renders as

this = *that

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you mean, HTML <em>in comments</em>? \* renders as *, though, so *escape* – Jan Dvorak Apr 12 '13 at 16:32
@JanDvorak: Comments are a different parser again. – Martijn Pieters Apr 12 '13 at 16:38
Then there's the multi-line chat parser... :-) – Jan Dvorak Apr 12 '13 at 16:39
@JanDvorak: The multi-line parser assumes no formatting, unless you indent 4 spaces, at which point it always formats with <pre>. – Martijn Pieters Apr 12 '13 at 16:40

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