Guide

Is this email a scam? Check it with Claude or ChatGPT in one minute

Phishing emails get through every filter sooner or later, and the good ones look exactly like the real thing. Desktop Steward adds an Email check: the AI reads one email you point at, checks the things humans cannot see (sender records, where links really go, how old the domain is) and tells you in plain words whether to trust it. It is off until you turn it on.

Step 1: turn it on

Email check is opt-in because it sends the text of one email to the AI. Open the Desktop Steward panel (menu bar or tray icon → Open panel, or ask Claude to “open the panel”), scroll to Features and switch on Email check. You can switch it off any time.

What leaves your computer: the headers, links and text of the single email you ask about, sent to the AI you are chatting with, plus the domain names in it, looked up in the public RDAP registry to learn how old they are. Nothing is stored.

Step 2: point at the email

On a Mac, click the email in Apple Mail so it is selected. The first time, macOS asks whether Desktop Steward may control Mail; allow it. On Windows, or if you read mail in a browser, save the email as a file: in Gmail open the ⋮ menu → Show original → Download original, then move the .eml file into Downloads.

Is the email I have selected in Mail real?

DANGER: this email shows signs of phishing. The sender calls itself “Apple Support” but writes from apple-id-support.com, not apple.com. DMARC failed. The link “appleid.apple.com” actually goes to secure-verify.ru, a domain registered 9 days ago. The attachment Invoice.pdf.exe is a program. The text pushes for action within 24 hours. Do not click, reply or open the attachment.

To sweep the inbox instead of one message, ask “check my last 10 emails for phishing”: you get one line per message (ok / suspicious / danger with the main reason) and details only for the flagged ones. On a Mac this reads the most recent inbox messages in Apple Mail, up to 25 at a time.

What the check looks at

  • Who really sent it. The display name against the real address, reply-to addresses on other domains, look-alike domains (paypa1.com, apple.com.secure-login.ru, non-Latin characters).
  • The mail server's own checks. SPF, DKIM and DMARC results from the headers: whether the sending server was allowed to use that domain.
  • Where links go. Link text that shows one site while the address goes to another, URL shorteners, bare IP addresses, logins hidden in links.
  • How old the domains are. A domain registered days ago is a strong sign; real companies' domains are years old.
  • Attachments. Programs and scripts, web pages (fake login forms), archives, Office files with macros, fake double extensions.
  • The wording. Urgency, threats to lock the account, requests for codes, passwords, gift cards or transfers, “keep this confidential”, generic greetings. The technical checks come from Desktop Steward; the reading of the request itself comes from the AI.

The verdict is Danger, Suspicious or Likely genuine, always with the reasons. “Likely genuine” means the technical side holds up; whether the request makes sense is still your call, and the AI will say so.

Step 3: act, carefully

On a Mac you can say “flag it” or “mark it as junk”. A confirmation window opens on your computer before anything changes, and nothing is ever deleted: junk mail stays in the Junk mailbox. If the email is from someone you know, call them on a number you already have, not one from the email.

Mark it as junk.

A window on your Mac asks: “Mark this email as junk in Mail?” Click Allow. The email is marked as junk.

Why not just rely on the spam filter?

Filters stop the mass mailings. The ones that reach you are the targeted ones: your name, your bank, a plausible invoice. Email check is a second opinion for exactly those, and it explains itself, so you learn what to look for next time. It is not an antivirus and it does not scan your mailbox; it only reads the email you ask about.

Questions

Does it work with Gmail or Outlook?

Yes. On a Mac, any account added to Apple Mail works (iCloud, Gmail, Outlook, work mail). Otherwise save the email as an .eml file and ask to check the file.

Does it work from ChatGPT?

Yes, through the Desktop Steward app and remote access: the same check_email tool is available to ChatGPT.

Can it read my whole mailbox?

No. It reads the one selected message, or the most recent inbox messages when you ask for a sweep (up to 25 at a time), and never stores anything.

Is it safe to send the email to the AI?

The email text goes to Claude or ChatGPT in the same way as text you paste into a chat. Do not use it on emails whose content must not leave your computer.

A second opinion before you click

Free on Mac and Windows. Turn on Email check in the panel and ask “is this email real?”.

Download for Mac or Windows