Email Delivery Troubleshooting

Diagnose why emails are not being delivered

🧪 Tested by a human Intermediate 👤 It Admin 👤 Support
Help me diagnose email delivery failure. Scenario: [DESCRIBE — emails not received / going to spam / bouncing / delayed]. Check: (1) Message trace in Exchange Admin, (2) SPF/DKIM/DMARC alignment, (3) Transport rules that might redirect, (4) Recipient mailbox issues, (5) IP reputation, (6) Content filtering triggers. Provide step-by-step diagnosis with Exchange admin paths.

Works on

⚡ M365 Copilot ⭐ ChatGPT (Best)

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🟢 ChatGPT

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Tips for Best Results

  • Message trace is your best friend for email issues
  • Check transport rules — they silently redirect more than you expect
  • SPF/DKIM failures cause legitimate emails to land in spam

📎 More Prompts

Blameless Post-Incident Report

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Write a blameless post-incident report for [INCIDENT]. Include: (1) Executive summary (2 sentences), (2) Timeline of events with timestamps, (3) Impact assessment (users, revenue, SLA), (4) Root cause analysis, (5) What went well in the response, (6) What could be improved, (7) Action items with owners and deadlines. Tone: factual, constructive, forward-looking.
⚡ M365 🟢 GPT ⭐ Claude

Diagnostic Decision Tree

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Create a diagnostic decision tree for [ISSUE TYPE — network connectivity / application crash / login failure / slow performance / email delivery]. Structure as: If symptom A → check B → if yes → do C, if no → check D. Include: expected outcomes at each step, escalation triggers, and resolution confirmations. Write for a Level 1 support technician.
⚡ M365 ⭐ GPT 🟠 Claude

End User Self-Service Fix Guide

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Write a self-help troubleshooting guide for [ISSUE] that a non-technical user can follow. Structure: (1) What you are experiencing (symptom description), (2) Try this first (easiest fix), (3) If that did not work, try this (next steps), (4) Still stuck? Contact IT (what info to provide). Use simple language, include where to click, and add helpful screenshots descriptions.
⚡ M365 ⭐ GPT 🟠 Claude
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