Security · 10 October 2026 · 15 min read
The invoice is real. The supplier is real. The conversation has been running for weeks between two people who know each other. Then the bank details change, in the same thread, in the same tone, and the payment goes to an account that belongs to neither company. This is the most profitable attack on business email today. It is also one of the most preventable, with controls most Microsoft 365 businesses already own.
A generic pattern, assembled from the public record and from incidents we have worked on. No single company is described.
Business email compromise is the second-costliest category of cybercrime reported to the FBI: almost $3.05 billion in reported losses in 2025, from complaints filed in the United States alone. Most of that money left through one scenario. Not a fake chief executive demanding a wire transfer, and not a crude phishing email, but a genuine invoice conversation that an attacker quietly joined and then redirected.
This article follows that scenario from the first stolen password to the moment the money is gone, because the defences only make sense once you see where each one would have broken the chain. The attack has four stages. Every stage has a control.
From one mailbox to one diverted payment
| Stage | What the attacker does | What you would see, if you looked |
|---|---|---|
| 1. Get into a mailbox | Usually a phishing page that relays the real Microsoft sign-in and steals the session, or a password bought from an infostealer. The mailbox can be yours, your supplier’s or your client’s; one is enough. | A sign-in from a hosting provider or a VPN exit, often at night, with no managed device. |
| 2. Watch and wait | Searches the mailbox for “invoice”, “payment”, “IBAN”, “remittance”. Reads the finance threads. Learns who pays whom, how much, when, and what the invoices look like. Creates inbox rules so replies about payments are moved out of sight. | New inbox rules that move mail to RSS Feeds, Archive or Conversation History, or delete it. Mailbox searches in the audit log. |
| 3. Move the conversation | Registers a lookalike of one party’s domain and sets up a mailbox on it with the same display name and signature. Forwards or replies to the live thread from the lookalike, so the thread continues with every earlier message quoted below. Sometimes both parties are moved to lookalikes, and neither is talking to the other any more. | A reply whose sender domain differs by one character from the one above it. An “External” tag on a sender who was internal yesterday. |
| 4. Change the bank details | When a genuine invoice falls due, sends the “corrected” invoice or a note that the account has changed, with a plausible reason: an audit, a new bank, a problem with the old account. Answers questions quickly and politely. Keeps the hidden rules in place so the real supplier’s chasers never arrive. | A change of payee details requested by email, with urgency, and with a reason not to call. |
The money is usually discovered missing when the real supplier chases the unpaid invoice, two to six weeks later. By then the receiving account has been emptied.
The attack does not break a technical control. It uses trust that already exists.
rn for m, l for i, a different ending, an added hyphen. Our next article covers lookalike domains on their own.The point of the table above is that the chain can be cut in four places. Cut it in all four and a single mistake stops being a disaster.
We have written about how a mailbox is taken over with MFA on, so briefly: MFA alone does not stop a relayed sign-in. What does is Conditional Access in Entra ID P1, which is inside Business Premium and Microsoft 365 E3. Require a managed device for mail, so a stolen session only works on a device enrolled in Intune. Protect MFA registration, so the attacker cannot add their own phone. Use phishing-resistant methods (passkeys, Windows Hello) for finance and administrators. Block the countries you do not operate in. If every mailbox in your supply chain were protected this way there would be no stage 2; yours can be.
The reconnaissance phase is where the attacker is most visible and most ignored. Three things catch it.
This is where Microsoft 365 does more than most people realise, and where most tenants have it switched off.
Set-ExternalInOutlook -Enabled $true, and every message from outside the organisation carries an External label in Outlook, Outlook on the web and the mobile apps. The moment a “colleague” in a thread acquires the tag, the thread has been moved. Mail flow rules that prepend “[EXTERNAL]” to the subject do the same job more crudely and should be retired before the native tag is enabled, or users see both.Everything above reduces the odds. One rule removes them: no change to a payee’s bank details is ever acted on from an email alone. It is confirmed by telephone, to a number the company already holds from before the request, never to a number in the email or in the email’s signature. The same rule applies to new suppliers, to “urgent” payments and to a director’s request from the road.
Written down, the policy fits on an index card:
Technology makes this rule easy to keep. It does not replace it. The companies we see lose money to this attack usually had a verification policy; what they did not have was a culture in which a junior accounts clerk felt able to delay a director’s urgent payment for a phone call.
Controls by plan
| Plan | What you can switch on | What you cannot |
|---|---|---|
| Business Basic and Business Standard | MFA; the External tag; blocking auto-forwarding; the built-in alert policies; spoof protection for your own domain. | No impersonation protection, no Conditional Access, no managed-device requirement. A stolen session works from anywhere. |
| Business Premium | All of the above plus Defender for Office 365 Plan 1 (impersonation protection for users and domains, mailbox intelligence, first contact safety tip, Safe Links, Safe Attachments), Entra ID P1 Conditional Access and Intune device compliance. | Risk-based automatic blocking; the longer evidence retention; anomaly detection on inbox rules. |
| Microsoft 365 E5, or the add-ons | Entra ID P2 risk policies that act on their own; Defender for Office 365 Plan 2 with Threat Explorer, automated investigation and attack simulation; Defender for Cloud Apps anomaly detection; Audit Premium with a year of retention. | — |
For most businesses under three hundred users, Business Premium is the right answer: every control in stages 1 to 3 is inside it, at a price per user per month that is a rounding error against one diverted invoice. What it does not include is the finance rule in stage 4, which costs nothing.
There is a second licensing question, and it is the one businesses discover too late. When a mailbox has been compromised, the investigation depends on logs that were being kept before anyone knew there was a problem. Audit licences cannot be bought after the fact: a record that was not retained is gone.
Two separate systems hold the evidence, and they answer different questions.
Purview Audit comes in two tiers, and the tier is a per-user licence, not a tenant setting. Each user whose activity you want kept at the higher tier needs the licence assigned to them.
Audit tier and retention, by licence
| Licence | Audit tier | Retention |
|---|---|---|
| Business Basic, Business Standard | Audit Standard | 180 days |
| Business Premium | Audit Standard | 180 days |
| Microsoft 365 E3 | Audit Standard | 180 days |
| Microsoft 365 E5 | Audit Premium | One year for Exchange, SharePoint, OneDrive and Entra ID records, by default; 180 days for other services unless a policy extends it |
| Business Premium + Microsoft Purview Suite for Microsoft 365 Business Premium | Audit Premium | One year, as above |
| Microsoft 365 E3 + Microsoft 365 E5 eDiscovery and Audit, or + Microsoft Purview Suite | Audit Premium | One year, as above |
| Audit Premium + 10-Year Audit Log Retention Add On | Audit Premium | Up to ten years, under a custom retention policy |
Audit Standard’s 180 days applies to records generated since 17 October 2023. Audit Premium also records finer events, such as which individual messages were accessed, that the standard tier does not.
Three caveats that Microsoft’s documentation is clear about and sales conversations often are not:
What we recommend. A business on Business Premium that wants long-term evidence for the accounts most likely to be targeted does not need to move everybody to Microsoft 365 E5. Add Audit Premium to the accounts that matter: directors, finance, anyone who approves payments or holds signing authority, and the administrators. On Business Premium that is the Purview Suite for Business Premium add-on, on the November 2026 European list €10.44 per user per month; on E3 it is E5 eDiscovery and Audit at €6.24 or the full Purview Suite at €12.48. If the requirement is “we must be able to reconstruct what happened in the managing director’s mailbox eighteen months ago”, add the 10-Year Audit Log Retention add-on, €2.08 per user per month, and write the retention policy the same day. Current prices are in our catalogue; these were correct when this was written.
Done this way, ten protected accounts cost less per month than one hour of the incident response they make possible, and the rest of the company stays on the licence it already has.
A thread hijack succeeds because each person in it does one reasonable thing: opens a link, replies to a known contact, pays an invoice that is due. The defences are not about making people suspicious of everything. They are about making the stolen password useless, making the watching visible, making the lookalike wear a label, and making one phone call compulsory before money moves.
Switching those controls on, in report-only mode first so that nobody is locked out, and investigating an incident that has already happened, is what our incident response and hardening service does. A phishing simulation tells you how your own staff respond to the lure before an attacker finds out. Contact us for an initial incident assessment and response estimate.
No. Those records prove a message came from the domain it claims. The attacker owns the lookalike domain, so their messages pass. Authentication stops someone forging your domain; impersonation protection and the External tag are what flag a domain that merely resembles it.
Either works for the attacker. If the lookalike imitates the supplier, the reconnaissance usually happened in the supplier's mailbox; if it imitates you, in yours. The investigation starts with the sign-in and audit logs of whichever side the lookalike copies, and both sides should check.
No. Defender for Office 365 Plan 1 is included, but user and domain impersonation, mailbox intelligence and the first contact safety tip are configured in an anti-phishing policy. The Standard preset switches them on; adding your key suppliers' domains and finance contacts needs a custom policy.
No. Audit Premium is licensed per user. Add it to the accounts that matter, typically directors, finance and administrators, through the Purview Suite for Business Premium add-on or, on E3, the E5 eDiscovery and Audit add-on; add the 10-Year Audit Log Retention add-on and a custom policy where you need more than a year. The policy keeps records from the day it is created, so do it before the incident, not after.
Sometimes, if the recall is raised within hours. The receiving account is usually emptied within a day. The call to the bank comes before the investigation, not after it.
Usually because the call went to the number in the email, or because the person who should have called felt unable to delay an urgent payment from a senior colleague. The number must come from a record that predates the request, and the delay must be expected and praised.