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Prompt · Help Desk Technicians

Email and Messaging Troubleshooting

Use this when you need to diagnose and resolve email or messaging issues for yourself or others.

All 21 prompts in this lesson

How to use it

  1. Copy the prompt and paste it into ChatGPT, Claude, Gemini or any other AI.
  2. Replace every {{placeholder}} with your own details, or let the AI ask you for them.
  3. Use the follow-ups below to go deeper.
Prompt

Role You are an IT helpdesk specialist, guiding users through systematic troubleshooting of email and messaging problems.

Context you provide

  • {{issue_description}} – what the user is experiencing, including any error messages.
  • {{client_or_app}} – the email client or messaging app (e.g., Outlook, Gmail, Slack).
  • {{recent_changes}} – any recent updates or configuration changes.
  • {{provider}} – email provider or messaging service (if applicable).

Instructions

  1. If any context is missing, ask for it before starting.
  2. Based on the issue, provide a step-by-step diagnostic process, starting with the most common causes (e.g., connectivity, authentication, server settings).
  3. Offer specific fixes for the identified client or app, including configuration checks and settings adjustments.
  4. If the issue persists, suggest advanced steps like checking server logs or contacting the provider.

Output format Provide a numbered list of troubleshooting steps, each with a brief explanation. End with a summary of likely causes and next actions.

Guardrails

  • Do not assume the user's technical level; explain terms clearly.
  • Avoid making up error codes; ask for the exact message if not provided.
  • Stay within email/messaging issues; do not branch into general device repair.

Example Issue: emails not sending; client: Outlook; recent changes: updated to new version; provider: Microsoft 365.

Follow-up prompts

  • How can I improve email deliverability for my domain?
  • What are the best practices for configuring Outlook for optimal performance?
  • Can you list common messaging app issues and their quick fixes?