You usually cannot tell whether a phishing email was written by AI just by reading its prose. A polished message can be malicious, and a typo does not prove one is. Judge the sender, the request, its fit with your relationship and normal workflow, and any link or attachment. If the request is unexpected or consequential, pause, verify it through a separate trusted channel, and report the message without clicking or opening anything.
How to assess a suspicious email
Phishing tries to get you to do something that benefits the sender: send money or confidential information, disclose a password, approve a sign-in, open a file, or visit a fraudulent site. AI can help produce fluent or personalized text, but writing quality alone is weak evidence of whether an email is genuine. Look at what the message asks you to do and whether that request makes sense.
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Check the request and its context
- Is the action expected? Treat an unexpected payment, bank-detail change, password request, confidential-data request, or file as a reason to stop and verify.
- Is the pressure unusual? Urgency, secrecy, or a demand to bypass the normal approval process deserves extra scrutiny, especially when money or access is involved.
- Does it fit the relationship and workflow? A familiar name does not make an unusual request safe. Consider whether this person normally contacts you this way and whether the request follows established procedures.
- Does the sender address match? Check the actual address and domain, not just the display name or logo. A lookalike domain can resemble the real one, and a real account may be compromised.
Check links and attachments without taking the bait
Do not click a message link, scan its QR code, open an unexpected attachment, or approve a sign-in prompt to investigate. If your organization permits it, inspect a link’s destination without opening it; if anything is unclear, go to the service using a known address or existing bookmark instead. The FTC’s small-business cybersecurity guidance recommends avoiding an included login link and contacting the person or company using a number you already know is correct.
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What to do when you receive a suspicious email
- Pause. Do not follow the request while you assess it. In particular, do not send money or data, enter credentials, open a file, or approve a sign-in solely because the email tells you to.
- Verify independently if the request might be legitimate. Navigate to the service yourself or contact the person through a phone number or channel already in your records. An email reply is not independent verification.
- Report the original message. At work, use your organization’s report-phishing button or the reporting route provided by IT or security. Keep the original message available so security staff can inspect and trace it; do not simply delete it unless your organization tells you to.
- Ask for help if you are uncertain. Contact IT/security or a trusted colleague through a separate channel rather than testing the message yourself.
For Microsoft 365 administrators, Microsoft recommends enabling user reporting and routing submissions to an administrator mailbox, Microsoft, or both. For external reporting, the FTC lists [email protected] and ReportFraud.ftc.gov. If personal or business data was exposed, follow the organization’s incident process and applicable reporting obligations; the FTC advises businesses to alert affected customers when their data was stolen and points affected individuals to IdentityTheft.gov for a recovery plan.
If you clicked, entered information, or opened a file
Tell IT/security promptly, even if you are not sure anything happened. Give a factual account of what you did and when. Report whether you opened a link or attachment, entered a password, approved a multifactor sign-in, ran software, sent a payment, or disclosed information. Preserve the original email and follow your organization’s instructions; prompt reporting gives responders a chance to limit further access.
If credentials or a sign-in may be exposed
Use your organization’s account-recovery process to secure the affected account and change a compromised password. Tell responders if you approved an unexpected multifactor-authentication prompt or reused that password elsewhere, so they can assess which accounts may be at risk. Do not rely on changing a password alone if the account or device may still be under an attacker’s control.
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If an attachment may have run malware
Tell IT/security what was opened or run and on which device. If malware may have run, disconnect the affected device from the network according to your organization’s procedure; the FTC also advises disconnecting a malware-infected device. Avoid trying to clean or investigate a work device on your own if that could interfere with your organization’s response.
If money or information was sent
Report the payment or disclosure immediately to the relevant internal team, such as finance, privacy, or security, as well as IT. Share what was sent, to whom, and when. The organization can then assess financial, account, data, and notification implications under its incident process.
What a small-business response should cover
Make reporting a prompt, blame-free process. The first questions should establish what happened and when, not why someone missed a warning sign. A responder can use the following sequence, adapting Microsoft’s published phishing-investigation workflow to the mail, identity, and endpoint tools in use:
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- Identify the message. Preserve the original email and establish its Message-ID and relevant headers where available.
- Determine delivery and reach. Use message trace or the equivalent mail-platform tool to check when it arrived, which recipients received it, and whether it was delivered, blocked, or otherwise handled.
- Scope user interaction. Establish who opened a link or file, submitted credentials, approved a sign-in, sent money, or disclosed data, and when.
- Assess exposure and follow-on activity. Check for credential misuse, unexpected identity or mailbox activity, endpoint alerts, forwarding rules, and related data access or transfer.
- Contain and remediate. Remove malicious copies where possible, secure or reset affected accounts, and handle affected devices under the organization’s incident procedures.
- Review controls and communicate. Investigate how the message got through, tune detection where appropriate, and meet applicable internal and external notification duties.
Microsoft’s anti-phishing tuning guidance recommends reviewing message headers and the Spam Filtering Verdict (SFV) in the X-Forefront-Antispam-Report field when investigating whether filtering was skipped. It also discusses reviewing false positives and false negatives, reporting messages, considering multifactor authentication, and auditing external forwarding rules. These are Microsoft-specific investigation examples; use equivalent evidence and controls for your environment.
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SPF and DKIM help receiving systems assess whether mail was sent through authorized infrastructure and whether signed message content is intact. DMARC checks whether the authenticated domain aligns with the visible From address. Together, these controls can help an organization identify spoofing of its own domain, but they do not certify that a request is safe. A lookalike domain may authenticate for itself, and a legitimate account can be compromised. Filtering and authentication are useful layers alongside user reporting and independent verification, not replacements for them.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.When an AI assistant reads the mailbox
Email processed by an AI assistant introduces a separate risk: malicious content may include instructions aimed at the assistant rather than the human recipient. Microsoft describes possible outcomes such as revealing mailbox information, misclassifying a message, producing a misleading summary, or taking an unwanted workflow action. A message can therefore be risky even when its visible text appears to address only a person.
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Microsoft documents a prompt-injection detection control in Defender for Office 365. It uses LLM classification alongside existing sender and message signals and considers visible and hidden content, forwarded threads, and normalized obfuscated segments. Detections receive a high-confidence phishing verdict under a prompt-injection detection technology label. Microsoft explicitly says the control is not meant to block every instruction-like phrase or serve as a general-purpose prompt-injection benchmark, so it is a product-specific defense-in-depth measure, not a universal guarantee.
Microsoft’s Phishing Triage Agent is an AI-assisted analyst tool for reported messages, not a consumer detector. Its documentation lists Security Copilot capacity, Microsoft Defender for Office 365 Plan 2, and required reporting and role configuration among the prerequisites. Analysts can inspect and provide feedback on its classifications and generated feedback. Availability and licensing can change, so administrators should check Microsoft’s current product documentation before planning around it.
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