Tried to Automate Phishing Email Reporting on macOS — Here’s Why It Fails (and What Actually Works)

ChatGPT Use cases and examples
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Hi all — I go by EdgeCaseRick here.

I wanted to share a real-world attempt to solve a seemingly simple task: automate phishing email reporting on macOS 15.5 using only native tools like Automator and Shortcuts.

Spoiler: it doesn’t work.
But the lessons were worth capturing — especially for anyone thinking ChatGPT or Shortcuts can streamline this.

:magnifying_glass_tilted_left: What I Tried to Build:

A keyboard-triggered shortcut (Control + R) that would:

  • Grab a selected phishing email in Apple Mail
  • Forward or report it to security agencies (APWG, US-CERT)
  • Include the original message or a .eml attachment

:cross_mark: What Doesn’t Work (in macOS 15.5):

  • Shortcuts can’t access selected Mail messages — no body, no sender, no metadata.
  • Shortcuts can’t trigger a “Forward” — only create a new message.
  • Automator AppleScript to save messages as .eml is now blocked by sandboxing.
  • Even when Shortcuts does run, it fails silently or opens multiple drafts and throws system errors.

:white_check_mark: What Does Work:

  • Manual forwarding.
  • Dragging the phishing message into a new email (adds headers + body).
  • Creating a contact group like “Phishing Reports” to pre-fill recipients.

It’s not sexy, but it works. And for now, it’s faster and safer than trying to automate something Apple doesn’t expose.

:speech_balloon: Why I’m Sharing This:

I spent hours iterating with ChatGPT and testing these flows — and I realized that AI-assisted automation needs to clearly flag what’s not possible in current OS versions.
Even well-intentioned help can lead users straight into a time-wasting wall if model suggestions are based on outdated or deprecated APIs.

If you’re trying to automate mail workflows on macOS, especially anything involving reporting, phishing, or .eml handling: be warned, you’re in for a fight — and it might not be worth it.

If you’ve found better workarounds (especially for interacting with Apple Mail safely), I’d love to hear them.

Thanks for reading.

—
EdgeCaseRick