Why does AI-generated text look weird when pasted into email on Mac?

Because copied AI text often includes rich HTML, inline styles, and list metadata. macOS email clients interpret that clipboard data differently, which can cause font changes, spacing issues, and broken bullets.

Why do bullets collapse when pasting into Outlook or Gmail on Mac?

Bullet lists rely on hidden structure. When that structure is stripped during paste—especially via Paste and Match Style or aggressive sanitization—email clients can only paste plain text, causing bullets to collapse.

Is Paste and Match Style the best fix for email formatting issues?

Paste and Match Style is effective for short replies, but it often removes list structure and emphasis. For emails with bullets or formatting, a clean-paste step works better.

What is the best way to paste AI text into email on macOS?

For short messages, Paste and Match Style is usually sufficient. For structured emails, use a clean-paste step that removes hidden styling while preserving paragraphs, simple lists, and emphasis.

Dec 2025 · 6 min read · macOS email workflows

Fix Weird Email Formatting When Pasting AI Text on Mac

You draft an email with ChatGPT, Claude, Gemini, or Copilot. The wording is fine.

Then you paste it into Apple Mail, Gmail, or Outlook for Mac — and it immediately looks wrong.

Fonts don’t match.

Spacing feels off.

Bullets turn into paragraphs or collapse.

Tested with: Apple Mail, Gmail (web), Outlook for Mac, Superhuman.

This guide is for macOS.

Quick answer (Mac)

Short replies: Paste and Match Style.

Emails with bullets or structure: Clean the paste before it hits your email client.

This happens every day: Use a native macOS clean-paste tool.

Key idea

The problem isn’t the AI draft. It’s the clipboard.

AI tools copy rich HTML and inline styles. Email clients on macOS all interpret that data differently.

When you paste AI-generated text into email on Mac, you may see:

Font switches in Apple Mail
Extra or missing line spacing in Gmail (web)
Bullets renumbering or collapsing in Outlook for Mac
Headings or emphasis you didn’t intend

The content reads fine. The formatting makes it look copied.

Why this happens on macOS

When you copy text from browser-based AI tools, your clipboard contains multiple formats at once: plain text, rich text, and HTML.

Each macOS email client sanitizes that data differently:

Apple Mail preserves styling, making imported fonts and spacing stand out.
Gmail (web) strips aggressively, sometimes flattening lists or adding odd spacing.
Outlook for Mac is fragile with list semantics, which is why bullets often collapse or renumber.

This is default behavior. You’re not doing anything wrong.

The paste methods Mac users actually rely on

Method comparison

Method	Keeps rich lists	Keeps rich formatting	Speed	Best for
Paste and Match Style	Sometimes	No	Very fast	Short replies
URL bar / TextEdit (plain text)	No	No	Medium	Occasional cleanup
Clean-paste tool	Yes (simple lists)	Mostly	Fast	Structured emails

Option 1

Paste and Match Style

Removes formatting and matches the surrounding email text.

Common shortcut in many Mac apps: Option–Shift–Command–V.

Good for short replies. Not reliable for lists or structure.

Option 2

URL bar or TextEdit (plain text)

Paste into the browser address bar or TextEdit (Format → Make Plain Text), copy again, then paste into email.

It works, but destroys structure and slows you down.

Option 3

Use a native macOS clean-paste tool

If AI-assisted email writing is part of your daily workflow, this is the least wasteful option.

Purifai cleans AI and web text before it reaches your email client. It strips hidden styles while preserving paragraphs, simple lists, bold text, and links — so pasted emails look native instead of copied.

If this only happens occasionally, you don’t need it. If it happens multiple times per day, it saves real time.

The AI draft isn’t the issue.
The clipboard is.

The takeaway

AI can write solid emails. macOS email clients just need cleaner input.

Editing wording is subjective.

Fixing formatting is a tooling problem.

Once you separate those two, email stops feeling broken.

Common paste failures (and fixes)

Bullets collapse in Outlook for Mac → Clean the paste or rebuild the list after Paste and Match Style.
Font switches in Apple Mail → Paste and Match Style.
Extra spacing in Gmail (web) → Strip imported HTML before pasting.
Lists renumber incorrectly → Avoid mixed list types or clean the paste.