Microsoft 365

Multi-factor authentication: the control that matters most, done properly

Multi-factor authentication is the single highest-impact security control available to a small business, and Microsoft has stated it blocks the overwhelming majority of automated account compromise attempts. But not all MFA is equal: SMS codes are meaningfully weaker than an authenticator app, and both can be defeated by an adversary-in-the-middle phishing kit that steals the session token rather than the password. For accounts that control money or administration, phishing-resistant methods — passkeys, FIDO2 security keys, certificate-based authentication — are the only reliable answer.

Key facts

  • MFA blocks the large majority of automated credential-stuffing and password-spray attacks.
  • SMS-based MFA is vulnerable to SIM swap and SS7 interception; it is still far better than no MFA.
  • Authenticator app push notifications are vulnerable to MFA fatigue attacks unless number matching is enforced.
  • Number matching is enabled by default for Microsoft Authenticator push notifications.
  • Adversary-in-the-middle phishing proxies can defeat both SMS and app-based MFA by stealing the session cookie.
  • Passkeys and FIDO2 security keys are phishing-resistant because the credential is cryptographically bound to the legitimate domain.
  • MFA on its own does not protect against a stolen session token — revoking sessions is a separate action.

Why MFA works, and what it does not solve

Passwords fail for structural reasons: people reuse them, breaches leak them, and attackers automate the guessing. MFA breaks that model by requiring a second factor the attacker does not have. Against the dominant threat — automated attacks using credentials from unrelated breaches — it is close to decisive.

What MFA does not do is protect a session that has already been established. If an attacker steals a valid session token, they are inside without ever presenting a factor. This is why incident response after a compromise must include revoking sessions, not just resetting the password and re-registering MFA. It is also why Conditional Access and sign-in risk policies add value on top of MFA rather than duplicating it.

The methods, ranked honestly

SMS codes are the weakest common method. A SIM swap — persuading a mobile network to move a number to an attacker-controlled SIM — defeats them entirely, and this is a documented, practised attack against people who hold valuable accounts. Nevertheless, SMS MFA is dramatically better than no MFA, and if the choice is SMS or an exemption, choose SMS.

Authenticator app codes (TOTP) are better: the secret lives on the device and is not transmitted. Push notifications are more convenient again, but introduced their own weakness — MFA fatigue, where an attacker who already has the password triggers approval prompts repeatedly at antisocial hours until someone taps Approve to stop the noise. Number matching, now the default for Microsoft Authenticator, largely closes this: the user must type a number displayed on the sign-in screen, which they cannot do unless they are the one signing in.

Phishing-resistant methods are a different category. Passkeys and FIDO2 hardware keys use public-key cryptography bound to the legitimate domain, so a proxy phishing site cannot relay the authentication — the credential simply refuses to work on the wrong origin. For administrators, finance staff and anyone who can move money, this is where you should be.

  • SMS — weakest, but still far better than nothing
  • TOTP authenticator codes — solid, no network dependency
  • Push with number matching — convenient, resistant to MFA fatigue
  • Passkeys / FIDO2 keys — phishing-resistant, correct choice for privileged accounts
  • Certificate-based authentication — strongest, generally overkill below enterprise scale

Adversary-in-the-middle, and why MFA alone is no longer sufficient for privileged accounts

The attack that has changed the calculus is the adversary-in-the-middle phishing kit. The victim clicks a link and reaches a proxy that renders the genuine Microsoft sign-in page. They enter their password, they approve the MFA prompt legitimately, and the proxy captures the resulting session cookie. The attacker replays that cookie and is inside, having never needed the password or the second factor again.

Nothing about SMS or app-based MFA prevents this, because the user genuinely authenticated — just on the wrong site. Only domain-bound credentials stop it, which is the practical argument for passkeys on any account that matters. Conditional Access with device compliance requirements also raises the bar considerably, because the stolen cookie is presented from an unmanaged device.

Rolling it out without a week of chaos

MFA rollouts fail on logistics, not on technology. The predictable problems are shared accounts nobody owns, service accounts embedded in scripts, staff without smartphones, and the people who are on leave during the enrolment window.

Run it in a deliberate order. Enrol IT and administrators first so they experience it before supporting it. Communicate a week ahead with a one-page explanation of what will happen and why, in language that does not assume technical knowledge. Give a two-week enrolment window and then enforce. Require every user to register two methods, which prevents the single most common lockout — a replaced phone with no backup method.

Have a documented, verified process for resetting MFA when someone is locked out, including identity verification that does not depend on the account they cannot access. An MFA reset request is a favourite attacker pretext, and a weak reset process undoes the entire control.

Offer people an alternative to their personal phone

A recurring and legitimate objection is staff not wanting a work authenticator on a personal device. This is worth taking seriously rather than overriding, because a forced rollout produces workarounds.

The usable alternatives are a hardware security key (a few pounds per user, no phone involved, and phishing-resistant into the bargain), Windows Hello for Business on a managed laptop, or a low-cost dedicated device for the handful of people who need it. Offering a hardware key to objectors frequently resolves the issue immediately and improves your security posture at the same time.

What businesses most often get wrong

  • Exempting directors and service accounts because enforcement was inconvenient
  • Allowing only one registered method, guaranteeing lockouts when phones are replaced
  • Leaving legacy authentication enabled, which bypasses MFA entirely
  • Treating MFA as complete protection and never revoking sessions after a compromise
  • Using a weak identity check for MFA reset requests, which hands attackers a route in
  • Relying on SMS for administrator accounts that can change billing or payment details

Where AlwaysOnIT fits — and doesn't

MFA resets and re-enrolment are core to what we do, and we perform an identity check before every one of them — that check is the security value of the process, not an obstacle to it. We will advise on method selection and rollout sequencing. We do not ship or manage hardware security keys, because we do not handle physical hardware at all.

Frequently asked questions

Multi-factor authentication — common questions

Is SMS multi-factor authentication secure enough?

It is better than no MFA by a wide margin, and it defeats ordinary credential-stuffing. It is weak against a targeted attacker because of SIM swap and interception risks. Use it as a fallback for staff who cannot use an app, and never as the primary method for administrators or anyone who can authorise payments.

What is an MFA fatigue attack?

An attacker who already has a valid password repeatedly triggers approval prompts, often overnight, until the user approves one to make the notifications stop. Number matching defeats it: the user must enter a number shown on the sign-in screen, which they cannot see unless they initiated the sign-in. Microsoft Authenticator enforces number matching by default.

What is phishing-resistant MFA?

Methods where the credential is cryptographically bound to the legitimate website domain, so it cannot be relayed through a proxy phishing site — passkeys, FIDO2 security keys and certificate-based authentication. Unlike codes or push approvals, they cannot be intercepted and replayed by an adversary-in-the-middle kit.

Can attackers get past MFA?

Yes, in three main ways: stealing a session cookie via an adversary-in-the-middle phishing proxy, SIM-swapping an SMS number, or exploiting a weak MFA-reset helpdesk process through social engineering. This is why MFA should be paired with session revocation procedures, phishing-resistant methods for privileged accounts, and a rigorous identity check before any MFA reset.

How should a small business handle MFA when someone loses their phone?

Verify the person's identity through a channel independent of the lost device — a callback to a known number or confirmation from their manager — then require MFA re-registration, revoke existing sessions in case the device is in someone else's hands, and have them enrol two methods on the replacement. Record who requested and approved the reset.

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