Why Markdown falls apart in an email, and what to do about it

Ask an assistant to draft a reply and you get Markdown, because that is what assistants write. Paste it into an email client and you get asterisks. The formatting that made the draft readable on screen becomes noise in the message.

Why it happens

Markdown is a source format. It only looks like formatting once something renders it. Your assistant’s chat window renders it; your email composer does not — it treats **Total cost** as five literal characters followed by a word followed by five more.

The same is true of applicant-tracking forms, most chat inputs, ticket fields and spreadsheet cells. Anywhere that accepts plain text, Markdown syntax arrives verbatim.

The part everyone gets wrong

The obvious fix is to strip the syntax characters. That is easy, and most online converters do exactly that — usually by reaching for a library that walks the document and removes formatting nodes.

The trouble is what those libraries do to lists. Given this:

1. **Preferred intake:** September 2027
2. **Total work experience:** 5 years
3. **Current role:** Operations analyst

a typical stripper returns:

Preferred intake: September 2027
Total work experience: 5 years
Current role: Operations analyst

The bold is gone, which is right. So is the numbering, which is not. If you were answering a numbered questionnaire, those numbers were the structure of your answer. The recipient asked question 7; without the number, nobody can tell which answer is question 7.

What good output looks like

Four things should survive a conversion into plain text:

1. Ordered-list numbering, including lists that do not start at 1.
2. Nested indentation, so a sub-point still reads as a sub-point.
3. Line breaks and paragraph spacing as you wrote them.
4. Anything a reader would need, including the URL behind a link — plain text has nowhere to hide an href, so it is either written out or lost.

Everything else is a judgement call, which is why they are settings rather than opinions. A heading with nothing left to make it a heading can be plain text, uppercase, or keep its #. A table can be aligned columns, tab-separated values, or label-and-value lines. None of those is universally correct; it depends where the text is going.

One more thing worth cleaning

AI-written drafts tend to carry typographic characters that look wrong in a plain-text field: curly quotes, en and em dashes, ellipsis characters, non-breaking spaces, and occasionally invisible zero-width characters that survive copy and paste and confuse whatever receives them.

Converting those to their ASCII equivalents — ", -, ..., an ordinary space — is usually what you want for an email or a form field, and it is on by default here for that reason. It is a switch, because a document you intend to typeset properly wants the real characters kept.

Try it

Paste your draft into the converter and pick the Email reply preset. It sets plain headings, hyphen bullets, ASCII punctuation and aligned tables, and leaves your numbering exactly where you put it.