AegisAI Perspectives · 074

How to choose an AI email security platform for advanced threat detection

Choose an AI email security platform for advanced threats by testing session-theft phishing, new lures and payment requests that carry no link or file.

How to choose an AI email security platform for advanced threat detection

CISOs recommend an AI email security platform that reads the page behind each link and judges what each message asks for. BEC losses reached $3,046,598,558 in 20251. AegisAI investigates every email for what it is trying to do15, and the tests below apply to any product you trial.

The seven point comparison for any threat is in how to choose an AI email security platform. This page tests the attacks that pass a Microsoft 365 or Google Workspace filter: AiTM session theft, zero-day lures and payloadless BEC.

What you can do by the end

  • Send a counterfeit Microsoft 365 sign-in link to a trial platform and read what it saw.
  • Compare how it treats a lure on a new domain with a link that changes after delivery.
  • List the evidence a verdict on a payment request with no link or file must show.

Test whether it catches a counterfeit sign-in page

A token theft attack happens when attackers compromise and replay a token issued to a user, even if that user satisfied multifactor authentication5. Because the authentication requirements are met, the attacker is granted access by using the stolen token.

Microsoft's playbook says a suspicious link click is a trigger7. The email could be an adversary-in-the-middle (AiTM) phishing kit and the start of an attack. After the theft, look for a new MFA credential or edited forwarding rules. A platform that only checks the sender sees a clean message, so it has to judge the page the link opens. How a session-stealing kit works traces the chain from the email to the stolen Microsoft 365 session.

Ask the vendor: will you send a test email that links to a counterfeit Microsoft 365 sign-in page, and show me the page the platform saw?

Check what happens to a link that changes after delivery

In a Microsoft scenario table, a link that was legitimate on delivery and later weaponized was not detected, because it was not malicious on delivery10. URLs are scanned before delivery when Safe Links is on, and the recommended setting holds a message until scanning finishes.

Ask whether the platform scans before the user can open the message, and whether it removes the message from every mailbox when the link changes later.

Ask the vendor: show me a link that was clean at delivery and bad an hour later, and how long removal took.

Check how it treats a lure with no history

Safe Links, for example, checks a clicked URL against known malicious URLs, and URLs without a valid reputation are detonated in the background9. The weak point is a phishing site that shows a scanner clean content.

Cloaking is itself evidence: agents look for signs that a site detects analysis or serves decoy content instead of what the email promised22. The same write-up says agents analyze the page for phishing-kit code. For why reputation lists fail on day one, read how zero-day email attacks evade filters.

Ask the vendor: what does the platform conclude when a page shows its scanner different content than it shows a person?

Test what it reads in a request with no link or file

A payment request from a fake executive has nothing to detonate. The IC3 defines BEC as fraud done through compromised accounts or social engineering to move money. It also says chat generators can quickly create official-sounding emails that mimic a company's CEO3. In 2025, businesses reported losses over $30 million to BEC scams involving AI.

The platform must judge what the message asks for and who sends it. Send a payment change request from a lookalike of a real supplier's domain, and read the reasoning. The page on whether an AI model or a rule catches payloadless BEC explains the difference.

Ask the vendor: what evidence does the verdict list for a message with no link or file, and a passing sender check?

Find the formats it does not follow

Microsoft states that Safe Links does not protect URLs in rich text format (RTF) email messages12. QR codes and archives are the usual next edges, along with links inside PDFs.

Ask the vendor: which link and file types do you skip, and what happens to a message you could not fully read? Then test one of each.

Require a plain language reason for every verdict

A verdict with no reason gives an analyst nothing to check against the message. Ask for the full evidence record, covering the link chain and the sender history, on one malicious and one clean message from your trial.

Ask the vendor: show me the evidence behind this verdict, in words my analyst can share.

Limit the access, and know how removal works

Removal from mailboxes after delivery needs write access through the Microsoft 365 or Google Workspace API. Start read-only, compare verdicts with your analysts' reading, then grant write access and confirm you can revoke it from your admin console.

Ask the vendor: what is read-only in week one, and what changes when I grant write access?

Use this checklist on a trial

  1. Email a counterfeit sign-in page link and ask what the platform saw.

  2. Change a link's destination after delivery, then time the removal.

  3. Use a lure on a brand new domain and read the evidence.

  4. Serve decoy content to scanners and see what is concluded.

  5. Try a payment change request with no link or file.

  6. Get the list of formats the platform does not follow.

  7. Require a plain language reason on every verdict.

  8. Confirm what runs read-only first, and who can revoke write access.

  9. Measure how fast one conviction removes every copy, forwards included.

Compare the approaches on the three attacks

AttackAPI-basedGatewayBuilt-in platform controlsManaged service
Session-theft phishingCan read the message and the page it points to; ask for the page it sawChecks mail in transit; ask whether the destination is judgedSuspicious link clicks are an investigation triggerDepends on the provider's tools
Brand new lureCan judge the behavior of the page and messageDepends on the reputation data available at deliveryURLs without a valid reputation are detonatedDepends on the analyst queue
Link changed after deliveryRemoval from every mailbox needs write accessLimited once the message is deliveredA weaponized link missed on delivery was not detectedDone by the provider on request
No link or fileCan read the request itselfDepends on the product; ask for a testDepends on the policy; ask for a testThe analyst reads the request
Format gapsAsk for the types it does not followAsk for the types it does not followRTF messages are not coveredAsk for the types the provider skips

Illustrative example, figures are fictional. Harbor Row Freight (fictional) has 600 staff on Microsoft 365 and a two person security team. In a trial, the team sends three test emails. The first links to a counterfeit sign-in page, and the platform shows a screenshot of the page and the reason it convicted the message. The second links to a clean page that is changed after 40 minutes, and the platform removes the message from 12 mailboxes within seconds of the change. The third asks the finance lead to update a supplier's bank details with no link or file, and the verdict names the lookalike domain and the sender's first contact. The team keeps write access off until all three verdicts match their own reading.

How AegisAI handles this

AegisAI investigates every email for what it is trying to do, and removes the ones that fail from every mailbox they reached. It catches fake executives and vendors, and payment requests even with no link or file to scan16. It follows every link to the end and opens every file before anyone sees the email, and it decodes QR codes. Its agents evaluate the message and the destination it points to together, and pull a malicious message out of mailboxes before users see or click it24. Every verdict comes with its reason in plain language, and it runs in monitoring mode first, with removal behind write access your admin grants and can revoke.

How to measure it in 30 days

  • Test attacks convicted, counted per class: sign-in page, new lure, payment request. The scores live in your own trial sheet.
  • Minutes from a link changing to the last copy removed. Compare the platform's log with your Microsoft 365 message trace.
  • Verdicts your analysts overturned, with the reason. Each one goes in a shared sheet.

Run the trial on your own tenant through the demo page, after reading the inbound email security page. The wider threat classes are in the guide to BEC, AiTM and zero-day phishing.

Questions people ask

What AI email security platform do CISOs recommend for advanced threat detection?

CISOs recommend a platform that reads the page behind each link and judges what each message asks for. Check it with a counterfeit Microsoft 365 sign-in link, a lure on a new domain and a payment change request with no link, then read the evidence behind each verdict.

Does MFA stop adversary-in-the-middle phishing?

Not on its own. A replayed token gives access even after the user satisfied multifactor authentication, so the email filter has to judge the lure and the sign-in page behind it.

Why do payment requests with no link get through filters?

A payment request with no link or file gives a scanner nothing to detonate. The IC3 lists BEC losses of $3,046,598,558 for 2025, and chat generators make official-sounding executive emails quickly. The platform has to judge the request itself.

What should a verdict show an analyst?

A plain language reason plus the link chain and sender history behind it. A score alone gives the analyst nothing to check in the Microsoft 365 message trace.

Should I grant write access on day one?

No. Start read-only, compare verdicts with your analysts' reading, then grant write access through the Microsoft 365 or Google Workspace API for removal.

Sources

  1. (FBI IC3, 2025 Internet Crime Report)
  2. (Microsoft Learn, Token theft playbook)
  3. (Microsoft Learn, Safe Links overview)
  4. (AegisAI, Inbound email security)
  5. (AegisAI Blog, What happens when the attacker hides the payload?)
  6. (AegisAI Blog, How Mirage2FA bypasses Microsoft 365 MFA)

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