Redefine Logic
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Must-see common situations
and a starting point for each one

“What do I do if…” — situations that arrive without warning, and where to begin with each. You will find the first steps to take, the reasoning behind it, and a candid assessment of how concerned you should realistically be.

Written to inform

Not to alarm you into a phone call. Where we think a risk is overstated, we say so.

Both halves of the job

Growing an organization and protecting it are the same discipline. Both are covered here.

It expands

Built from situations people bring to us. Send us yours and we will add it.

If something is happening right now — money is moving, or systems are locked — filter to “Happening now” below, then telephone someone before you act. Involving a second person is the most underrated control available, and it costs nothing.

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Please read before acting on anything below

This page provides general education, drawn from our own experience and from published research. It is not advice concerning your particular circumstances, your systems, your contracts or your legal obligations, and it cannot be, since we have visibility into none of those.

Treat each scenario as a starting point for your own research rather than as an instruction. Verify anything consequential independently, and where money, data, personnel or regulators are involved, obtain qualified professional advice before acting. You proceed at your own risk, and responsibility for the outcome remains with you.

Circumstances differ in ways that change the correct answer entirely. A course of action that suits a sole proprietor may be wrong for a regulated practice carrying an insurance policy and a statutory notification duty.

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Show Urgency
Nothing matched that. Try fewer words, or describe it differently. If it is a situation we have not covered, tell us — that is how this page grows.
Protect

When something has already happened

Ordered roughly by how fast you need to move. The red ones are where minutes matter.

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We arrived this morning to find everything locked and a screen demanding payment in cryptocurrency. What should we do?

Right now, in this order

1. Disconnect from the network, but do not power anything off. Unplug the network cable and disable Wi-Fi, then leave the machines running. Shutting down destroys evidence investigators will need, and some variants cause further damage on reboot.

2. Photograph the ransom screen using your phone. Capture the note itself, any reference or identifier it displays, and the altered file extensions. You will need all of it.

3. Contact your cyber-insurance provider before anyone else. Most policies require you to engage their approved incident responders. Bringing in your own IT firm first can invalidate the claim entirely.

4. Do not pay, and do not decide alone. Not yet, and certainly not within the first hour.

What follows, and the mistakes that prove most costly
The next steps
  1. Assume the data was stolen as well as encrypted. Current ransomware copies data out before locking it, specifically so that paying for a decryption key does not resolve the matter. This turns an IT outage into a probable privacy breach.
  2. Establish your notification obligations early. In Canada, a breach presenting a real risk of significant harm must be reported to the Privacy Commissioner and to the individuals affected. If you hold health information in Ontario, PHIPA obligations apply in addition. Both carry deadlines.
  3. Report the incident to the Canadian Anti-Fraud Centre and to your local police. This rarely recovers anything directly, but it is how the case evidence that eventually disrupts these groups is assembled.
  4. Check whether a free decryption tool exists. The No More Ransom project, operated by Europol with industry partners, publishes free tools for many strains. It is worth ten minutes before any conversation about payment.
  5. Do not restore from backup yet. Rebuilding before anyone has established the point of entry restores you directly into a compromised environment, frequently with the attacker still holding valid credentials.
Why these particular steps

The instinct is to resolve the situation quickly and quietly. Almost every expensive error in a ransomware incident originates in that instinct: powering machines down, wiping and rebuilding, paying early, or engaging a responder the insurer has not approved.

The insurance point is the one that catches organizations out most often. Cyber policies generally name a panel of firms you are required to use. Organizations routinely do the apparently sensible thing, call their usual IT support, and discover weeks later that the claim will not be paid.

On the question of paying

We will not tell you never to pay. That decision belongs to you and your counsel, and some organizations genuinely have no other route to survival. What we will tell you is what payment does not achieve: it does not un-steal the data, it does not remove your notification obligations, and decryption tools supplied by attackers are frequently slow and incomplete.

How serious is this?This is the worst day an organization has, and it is survivable — but only on the strength of preparation made beforehand. Tested, immutable backups and a printed incident plan are the difference between a difficult fortnight and closing the business. If you are reading this before it happens, that preparation is the work.
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My manager just phoned asking for an urgent payment. It sounded exactly like them, but the request is completely out of character. What do I do?

Right now

1. Do not act on the request, even partially. Preparatory steps such as drafting the transfer or assembling the paperwork feel harmless, but each one commits you a little further.

2. Hang up and call back on a number you already hold. Use the details in your own records, never a number offered during the call or supplied in a follow-up email.

3. If you cannot reach them, bring in a colleague before going further. Authorization is not the point. A second person interrupts the pressure the caller depends on, since every version of this attack needs you alone with the decision.

Why the voice was convincing, and how to prevent a repeat
Why the voice was convincing

Cloning a voice now requires only a few seconds of source audio, rarely difficult to obtain: a podcast appearance, a recorded talk, a voicemail greeting, a video on your own website. The tools are cheap, fast, and no longer distinguishable by ear. Recognizing a voice has stopped functioning as verification.

The audio is not the attack itself. Urgency, authority and secrecy are. Requests of this kind arrive time-critical, come from someone you would hesitate to challenge, and often carry a confidentiality wrapper — an unannounced transaction, or a matter the wider team must not learn about. The wrapper exists solely to discourage you from checking.

If money has already moved
  • Call your bank immediately and use the word “fraud”. Recovery prospects fall sharply with every hour.
  • Report the incident to the Canadian Anti-Fraud Centre, and to police once funds have left the account.
  • Preserve the evidence: time of the call, originating number, any follow-up correspondence, and the exact wording used.
  • Tell your team the same day. One person targeted usually means several were.
Making sure it fails next time

Agree a verification habit now, while nothing is happening. Two measures, both free:

  1. A call-back rule. Any payment request arriving by phone, message or email gets verified on a channel the requester did not choose. Apply it without exception at senior levels — particularly at senior levels, since senior authority is precisely what gets impersonated.
  2. An agreed passphrase, set in person, known to everyone who can move money. It sounds trivial until the day it prevents a six-figure loss. Worth having at home too, since the version aimed at elderly relatives is now widespread.

One point deserves saying out loud to your team: nobody should ever face criticism for slowing a payment down to check it. A culture penalizing hesitation builds the vulnerability in-house.

How serious is this?Serious. These attacks are active, growing, and no longer require technical skill. They are also almost entirely preventable by one procedural habit costing nothing. Of everything on this page, a call-back rule buys the largest reduction in risk for the least effort.
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An invoice has arrived from a supplier we genuinely use. Everything appears correct, but the email address is slightly different and the banking details have changed.

Right now

Do not pay it, and do not reply to it. A reply confirms that a person is reading, and it reaches the sender rather than your supplier.

Telephone your supplier on the number you held before this email arrived — from your own records, an earlier invoice, or their website reached by your own navigation. Never the number printed on the new invoice.

Ask one specific question: have your banking details changed? The answer is almost always no, and in most cases your supplier has no idea this is happening.

What is actually taking place, and why every detail looks correct
Why it looks so convincing

Because it generally is genuine. In most cases this is a real invoice. Either your supplier’s mailbox has been compromised and someone is monitoring the thread, or a legitimate invoice was intercepted, the banking details altered, and the document resent from a near-identical address.

This is why conventional advice fails here. The logo is correct, the amount is correct, the reference matches genuine work, and the tone is right because earlier correspondence was available to copy. The only incorrect detail is the one that moves the money.

The address substitution

Examine the domain closely. A single letter transposed, a hyphen inserted, .co in place of .ca, or rn standing in for an m. On a phone screen, under time pressure, these are effectively invisible, which is precisely the intention.

What to do next
  • Warn your supplier properly. If their mailbox is compromised, every one of their customers is receiving the same thing, and you may be the first to tell them.
  • Check your own sent items and mail rules. This operates in both directions. Look particularly for forwarding rules you did not create, since a common tactic is a rule that quietly conceals the attacker’s replies from you.
  • If payment has already been made, call the bank within the hour and use the word “fraud”, then report it to the Canadian Anti-Fraud Centre.
The rule that closes this category

Every change to banking details is verified by telephone, on a known number, without exception. No allowances for long-standing suppliers, for urgency, or for a plausible explanation about changing banks. Write the rule down, give it to whoever processes invoices, and make it entirely routine.

How serious is this?This is the attack that genuinely empties small business accounts, with both higher frequency and higher average losses than more dramatic threats. If you improve only one process this year, make it the one governing changes to banking details.
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An invoice has arrived from a company I have never heard of. Should I simply ignore it?

Right now

Do not open the attachment, and do not click anything within it. The invoice may not be the objective; frequently the attachment is.

Confirm that nobody in your organization placed an order before concluding it is fraudulent. If no one did, delete it, or report it to your IT provider if you have one.

Two quite different scams use this disguise
Which one you are looking at

Malware delivery. The attachment is the payload and the invoice merely supplies a reason to open it. Anything prompting you to “enable content” or “enable macros” falls into this category without exception.

Or straightforward opportunism. Plausible invoices for modest sums, sent in volume, on the expectation that a busy finance team will pay without checking. Domain renewals, directory listings and office supplies are the standard pretexts, and the amounts are deliberately kept low enough to avoid scrutiny.

If someone has already opened it

Treat it as a possible infection rather than an inconvenience. Disconnect that machine from the network and have it examined before it is reconnected.

How serious is this?Low, provided nobody opened the attachment. The real risk lies in volume: send enough of these to a busy office and eventually one is paid or opened. Well-configured email filtering removes the majority before anyone has to make a judgement.
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I received an email telling me to reset my password, but I never asked for a reset. What should I do?

Right now

1. Do not click the link. Not to inspect it, and not to “cancel the request”. If the email is fraudulent, the button is the entire attack.

2. Go to the service directly, typing the address yourself or using your own bookmark, then sign in as normal. Any genuine problem will be visible there.

3. While signed in, change the password and review which devices have access. If the reset request was real, someone has your address and is actively attempting entry.

Both possibilities deserve attention, for quite different reasons
If the email is fraudulent

The more common case. The message is a lure, the link leads to a convincing replica of the login page, and entering your password there hands it over directly. Read the domain following the @ rather than the display name, and disregard the padlock on the fraudulent site: certificates are free and prove nothing about intent.

If the email is genuine

This possibility gets dismissed as spam far too readily. A legitimate reset email you did not request means someone entered your address on the login page and selected “forgot password”. Nothing has succeeded yet. An attack is in progress, and you are being notified of it.

Where the messages continue arriving, treat the pattern as targeting rather than noise.

What to do next
  • Enable proper two-factor authentication if you have not already, using a passkey or authenticator app in preference to SMS.
  • Check mail forwarding rules and filters. A rule you did not create, quietly copying or concealing messages, is a reliable sign someone already has access.
  • Review the recovery email address and phone number on the account. Altering these is usually an attacker’s first action once inside.
  • If the account is your primary email, treat it as urgent. A primary mailbox can reset most of your other accounts, making it the master key and warranting your strongest protection.
How serious is this?Mildly serious, but do not ignore it. Ninety-nine times out of a hundred it is phishing you can safely delete. The hundredth is an early warning, and five minutes spent visiting the site yourself is what tells the two apart.
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My AI assistant has started asking for personal information and behaving oddly. Is something wrong?

Right now

1. Provide nothing. No passwords, no card numbers, no verification codes. A legitimate assistant requires none of these, neither to “confirm your identity” nor to “continue”.

2. Do not follow links it produces, and do not run any command or script it asks you to run.

3. Begin an entirely new conversation. Do not continue the existing one, since whatever is directing the behaviour resides within that thread.

The likely explanation, and why the model has not “gone rogue”
The likely cause

In most cases the cause is prompt injection. Instructions are concealed inside content the assistant reads on your behalf: a web page it browsed, a document you uploaded, an email it summarized. The assistant cannot reliably separate your instructions from instructions buried in the material, so it follows both.

The behaviour change is therefore often sudden and tied to a specific moment, immediately after the assistant opened a link, read a file or processed a message. The hidden text may be invisible to you, rendered white on white or placed in metadata.

The warning signs
  • A sudden shift in tone or persona mid-conversation
  • Requests for credentials, codes or payment details
  • Pressure toward a particular link or download
  • Claims of a rule change, an account problem or a deadline
  • Evasiveness about its most recent instructions
The part that matters most

Establish what the assistant was connected to. Where it holds access to your email, files or calendar through an integration, the exposure extends well beyond an unusual conversation. Review connected applications and revoke anything you do not actively require.

Review what you pasted earlier in the thread. If client data, credentials or confidential material went in before the behaviour changed, treat it as potentially disclosed and respond accordingly.

Then report the incident to the vendor. These problems get fixed because people report them.

How serious is this?More serious than most people currently assume, and genuinely early in its development. Prompt injection has no complete remedy yet; it remains an open research problem rather than a bug awaiting a patch. The practical defence is straightforward: never give an assistant a secret, and be deliberate about what you connect it to.
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My mouse just moved on its own. I also saw a black window flash up for a second. Should I be worried?

Right now

1. If the cursor is moving while you watch, disconnect from the network immediately. Unplug the network cable or switch off Wi-Fi. This is the one situation where speed matters more than preserving evidence, because someone may be operating the machine in real time.

2. Do not power the machine off, and do not start closing things. Leave it running once it is off the network. Shutting down destroys the record of what was happening.

3. Record it on your phone. A cursor moving by itself is one of the few incidents you can actually capture, and it will matter enormously to whoever investigates.

4. Telephone your IT provider on a number you already hold and ask one question: is anybody connected to this machine right now? Most of the time the answer is yes, and the whole thing resolves in under a minute.

Telling routine maintenance apart from somebody else at the keyboard
The honest starting point

Most of the time this is benign, and we are not going to pretend otherwise. Remote support sessions, overnight patching, a wireless mouse on a glossy desk, a laptop trackpad catching a sleeve. Scheduled tasks and software updaters open and close console windows constantly, and on a managed machine that happens several times a day.

Which is precisely the difficulty. These events are common enough that people learn to ignore them — so the one occasion it is not routine gets ignored along with all the others.

The distinction worth learning

Stop trying to judge whether the behaviour looks suspicious, because legitimate remote support and a hostile operator produce identical symptoms. The cursor moves the same way either way.

Ask instead whether anyone will take responsibility for it. Authorized work is announced, ticketed and attributable — a person can confirm it on the phone. Unauthorized access is the same behaviour with nobody owning it. Attribution is the test, not appearance.

Points toward routine
  • Someone confirms it. Your provider has an open session and a ticket.
  • During working hours, shortly after you reported a fault.
  • The console window appeared at login or on a schedule, not while you were mid-task.
  • Movement looks like drift or jitter rather than navigation.
  • A notification or toolbar appeared saying a session was active.
  • It stops when you lift the mouse off the desk or unplug it.
Points toward a problem
  • Nobody can account for it. No ticket, no session, no explanation.
  • Outside hours, or while the office is empty.
  • The cursor moves purposefully — opening folders, email, banking, password managers.
  • It began right after you clicked a link, opened an attachment, or took an unexpected support call.
  • Remote access software is installed which you do not remember installing.
  • Your screen blanks, or the machine logs you out while you watch.
On the terminal flash specifically

A console window appearing for a fraction of a second is usually a scheduled task, a login script, a software updater or policy processing. Benign by a wide margin.

The thing worth noticing is timing. A flash at login or on the hour is almost certainly housekeeping. A flash immediately after you opened a document, clicked a link or connected a device is a different matter, because a brief console window is exactly what a script running once looks like.

On the USB question

Autorun has been disabled by default on Windows for many years, so the classic “plug it in and it infects you” is largely historical. The replacement is worse and less known: devices built to look like a memory stick while identifying themselves to the computer as a keyboard, then typing commands faster than you can read. Nothing warns you, because as far as the machine is concerned a person is typing. That produces exactly these symptoms. See the car park USB scenario above.

If nobody can explain it
  • Keep the machine off the network until someone competent has looked at it.
  • Change passwords from a different device, starting with email, and sign out all sessions. Do not type a password into the machine in question.
  • Check for remote access software — and check whether your provider recognizes the one they find. Attackers increasingly abuse the same legitimate remote tools IT departments use, precisely because nobody questions them.
  • Review mail rules and forwarding, which is where this usually leads next.
  • Say something to your team the same day. Where one machine is affected, others are worth checking.
The cultural part, which matters more than the technical part

Someone noticed a cursor move and asked. That instinct is worth more than any product you could buy, and it survives only in an organization where asking is free.

Tell your staff plainly: nobody will ever be made to feel foolish for reporting something odd, including when it turns out to be nothing. The alternative is a team that stays quiet for a week, and a week is a very long time.

How serious is this?Usually nothing, occasionally the earliest warning you will ever get. The cost of checking is one phone call; the cost of assuming is measured in weeks of undetected access. Make the call, and be visibly pleased when the answer is “that was us”.
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Someone called claiming to be our bank, our vendor, our IT company. How do we know what is real anymore?

Right now

1. Assume the caller ID is wrong. The number displayed on your phone is supplied by whoever placed the call, and it can be set to anything. Your bank’s real number appearing on screen proves nothing whatsoever.

2. End the call and dial back on a number you obtained yourself — from the back of your bank card, a previous invoice, or the organization’s website reached by your own navigation. Wait a few seconds before dialling, or use a different phone, since a held line can be kept open.

3. Give out nothing in the meantime. No passwords, no verification codes, no card details, and no remote-access session. A genuine institution will wait while you call back. Anyone who objects to you verifying has told you what they are.

How to tell real from fraudulent, when everything can be faked
The honest position

You cannot reliably authenticate an inbound call. Caller ID is forgeable, voices can be cloned from seconds of audio, and the caller may know your address, your recent transactions and the name of your account manager, because that information leaks constantly through breaches.

Stop trying to detect fraud and change the direction of the call instead. Verification works when you initiate contact through a channel you selected. Every other test can be defeated.

What genuine organizations never do
  • Ask for your password or PIN. No bank, no vendor and no legitimate IT provider needs either.
  • Ask you to read out a verification code. A code arriving by text exists to prove your identity to the service, not to a caller. Reading it aloud hands over your account.
  • Ask you to move money to a “safe account”. No such procedure exists anywhere in Canadian banking. The phrase is diagnostic.
  • Require remote access to resolve an unsolicited problem. Particularly where they called you.
  • Insist you stay on the line while completing a transaction, or discourage you from consulting anyone.
Why the pressure feels so convincing

Urgency exists to prevent verification. Fraud on your account, a compromised server, a payment failing within the hour: each pretext creates a reason to act before checking. Treat urgency itself as the signal, independently of how plausible the story sounds.

Building the habit across the organization

Give every member of staff explicit permission to hang up. Most people comply with an authoritative caller because refusing feels rude, and fraud relies on that politeness far more than on technical skill. A stated policy removes the social cost of ending the call.

Agree one line everyone can use: “I will call you back on our published number.” Nobody needs to accuse anyone of anything, and the fraudulent call ends immediately.

How serious is this?Serious and rising, since voice cloning has removed the last informal check most people relied on. It is also among the cheapest risks to reduce: a call-back rule costs nothing and defeats nearly every version of the attack. Related: the scenario above covering a call that appears to come from your own manager.
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We keep getting strange texts, QR codes and Microsoft login prompts nobody requested. Are these attacks?

Right now

1. Approve nothing you did not personally start. An unexpected Microsoft or Google sign-in prompt means someone is attempting to enter your account at that moment, holding a password which works. Approving it grants them access.

2. If prompts keep arriving, change that password immediately and sign out of all sessions. Repeated requests indicate someone persisting until you tap approve out of irritation, a technique known as MFA fatigue.

3. Do not scan unexpected QR codes, and do not follow links arriving by text. Open the service directly instead.

Three separate techniques, and why each one works
Text messages

Phishing by text succeeds because phones compress everything. Links are shortened, the sender is a bare number, and people read messages while walking. A delivery notice, a toll charge, a tax refund, a message from the boss who has “lost their phone” — all low-effort, all effective at volume.

QR codes

A QR code conceals its destination completely, which is the entire problem. You cannot inspect the domain before committing, and phones often open the page without an intermediate confirmation. Printed codes placed over genuine ones in car parks, on parking meters and on restaurant tables are now a documented pattern.

Treat a QR code in an email as a straightforward red flag. Legitimate senders who already have your email address have no reason to route you through a camera.

Login prompts you did not trigger

The most serious of the three, because it confirms your password is already compromised. Multi-factor authentication is doing precisely its job at that moment, and the attacker is waiting for you to undo it.

Where available, switch to number matching or a passkey. Number matching requires you to type a digit shown on screen, which cannot be satisfied by a reflexive tap. Passkeys remove the approval step altogether.

What to do next
  • Report the messages to your IT provider or administrator, rather than simply deleting them. One person receiving these generally means a campaign is running against the organization.
  • Check mail rules and connected applications on any account that produced an unexpected prompt.
  • Tell staff that reporting is always welcome, including after they have already clicked. The interval between a click and a report determines nearly everything about the outcome.
How serious is this?The texts and QR codes are a nuisance you can train people past. The unrequested login prompt is genuinely urgent, because it tells you a working password is already in someone else’s hands. Treat the first two as hygiene and the third as an incident.
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Some of our computers are old but still work perfectly well. Do we really need to replace them?

The question to ask instead

Not “does it still work”, but “does it still receive security updates”. Those are entirely different questions, and only the second one carries risk. A ten-year-old machine running a supported operating system is far safer than a four-year-old machine running one the vendor has retired.

Check the end-of-support date for each operating system you run, then list which machines are already past it and which pass within the next twelve months. The exercise takes an afternoon and usually produces one genuine surprise.

What actually changes on the day support ends
Nothing visible, which is the difficulty

The machine behaves exactly as it did the previous day. What stops is the supply of security patches. From that point every newly discovered flaw remains permanently open, and those flaws are published in public databases that attackers read as a shopping list.

An unsupported system therefore does not degrade gradually. It accumulates known, documented, unfixable weaknesses, and the gap widens every month it stays in service.

It extends well past operating systems
  • Routers and firewalls. The most consequential category, since these face the internet directly. Internet-facing edge devices have become a leading route into organizations, and consumer routers typically stop receiving firmware updates after a few years without any notification.
  • Phones and tablets. Android devices in particular often stop receiving security patches while still functioning normally.
  • Applications and plugins. An abandoned plugin on your website is the same problem in a different place.
  • Printers, cameras and anything else holding an IP address. Rarely inventoried, almost never updated.
A practical order of replacement

Start with whatever faces the internet, because an exposed device can be reached by anyone without requiring a mistake from your staff. Replace the router or firewall first, regardless of how well it appears to run.

Then take the machines holding sensitive data. Client records, patient information, payroll, financial systems.

Everything else can wait, and often should. A machine with no network access and no sensitive data on it is a genuinely low priority. Replacing hardware that works is a real cost, and we are not going to pretend otherwise.

If replacement is not affordable this year

Reduce what the device can reach. Take it off the main network, remove its internet access, revoke its access to shared drives, and limit it to the single task requiring it. Isolation is a legitimate control, not a compromise, and for small organizations it is frequently the correct answer.

How serious is this?More serious than it appears, and genuinely under-appreciated. End-of-life equipment rarely causes the incident by itself, but it is repeatedly what turns a contained problem into an uncontained one. The internet-facing devices are the urgent part. A desktop in the corner running an old operating system with no network access is not worth losing sleep over.
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We have antivirus installed. Is that not enough?

The short answer

It is necessary and no longer sufficient, and the reason is worth understanding. Traditional antivirus compares files against a list of known-bad signatures. It is excellent at catching threats somebody has already catalogued, and blind to anything assembled this morning.

The attacks that matter to small organizations mostly involve no malicious file at all. Someone signs in with a working password, creates a mail rule, and sends an invoice. No antivirus product was ever designed to see that, because nothing malicious was downloaded.

What the acronyms mean, and which one you actually need
Plain definitions
  • Antivirus matches files against known signatures. Fast, cheap, and limited to the already-known.
  • EDR — Endpoint Detection and Response. Watches behaviour rather than files. A process encrypting documents in bulk looks wrong whether or not anyone has seen that program before. It also records what happened, so an investigation afterwards is possible.
  • XDR — Extended Detection and Response. The same idea widened across email, cloud accounts and network, so signals can be correlated. A suspicious sign-in plus an unusual mail rule plus an odd process forms a story no single tool sees.
  • MDR — Managed Detection and Response. Any of the above with human analysts watching it around the clock.
The distinction nobody explains

Detection without response is an alarm in an empty building. Most small organizations that buy EDR never configure anyone to answer it, and alerts arrive at 3am into a mailbox nobody opens until Monday. If nobody will respond, MDR is the honest purchase, and if MDR is unaffordable, say so and plan around it rather than buying the alarm alone.

What to do before spending anything

Several measures reduce risk further than an endpoint product and cost nothing: multi-factor authentication everywhere, removing administrator rights from daily accounts, a tested backup, and a rule governing changes to banking details. An organization without those should fix them before buying detection software, because detection assumes an attacker who got in, and those four reduce how often one does.

How serious is this?Worth addressing, though not before the free controls above. Built-in protection on current Windows and macOS is genuinely capable now, and anyone describing it as worthless is selling something. The real gap is not the product you run but whether anybody is positioned to act when it reports something.
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How many computers, phones and tablets are actually connected to our organization?

Where to begin

Most organizations cannot answer this, and the inability is itself the finding. You cannot patch, protect or remotely wipe equipment nobody has recorded, so every unknown device is by definition an unmanaged one.

Start from accounts rather than hardware. Open your Microsoft 365 or Google Workspace admin console and review the sign-in and device lists for each user. Mail accounts reveal phones nobody registered, and the exercise usually surfaces several devices the organization did not know existed.

Building a usable inventory in an afternoon, and the equipment everyone forgets
Four places to look
  • Your identity provider. Microsoft 365 and Google both list every device signed into each account, including personal phones collecting work email.
  • The router or firewall. Its connected-devices table shows everything currently on the network, printers and smart televisions included.
  • Twelve months of purchase records. Laptops bought and issued without ever reaching an asset list.
  • Your staff. Simply ask what people use for work. Framed without blame, the answers arrive quickly and reveal more than any scan.
The equipment consistently missed
  • Phones belonging to departed staff, frequently still receiving organizational email months after the person left.
  • Shared devices — the reception tablet, the laptop in the meeting room, the machine attached to a piece of equipment.
  • Household devices used for work, including a partner’s laptop borrowed during a busy week.
  • Printers, cameras and door controllers, each holding an address on your network and almost never updated.
  • A server or appliance nobody has switched off, running an application retired years ago.
What a useful inventory records

A spreadsheet is entirely adequate. Device, who holds it, operating system and version, whether updates install automatically, and what organizational data it can reach. The final column is the one carrying value, since a phone holding only calendar access presents a different problem from a laptop with the shared drive mapped.

Review it when someone joins and when someone leaves. Those two moments account for most of the drift.

On personal devices

Permitting staff to use their own phones is reasonable and widespread. The requirement is a documented position rather than a prohibition. Decide what personal devices may access, require a screen lock and current updates as a condition, and establish how access gets removed when someone leaves. Without a stated position, personal devices accumulate access silently and nobody can describe the exposure.

How serious is this?Not urgent, and genuinely foundational. An inventory prevents nothing by itself, yet every other control depends on it: you cannot confirm patching, enforce encryption or revoke access across equipment you have never listed. Of all the unglamorous work available, this one unlocks the most.
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How quickly do we really have to patch things?

The honest answer, by tier

Anything facing the internet: days, not weeks. Firewalls, routers, VPN appliances and remote-access gateways. Exposed edge devices have become a leading route into organizations, and a flaw in one can be reached by anyone without a single mistake from your staff.

Everything else: enable automatic updates and stop deliberating. For organizations without a dedicated IT team, automatic updating outperforms any schedule a person will actually maintain.

Why speed matters more than coverage, and what to prioritize
You cannot patch everything, and nobody does

Any organization running more than a handful of systems carries a backlog permanently. Treating every vulnerability as equally urgent guarantees paralysis, so the discipline lies in sequencing rather than completeness.

Three questions ranking any given patch
  1. Can the system be reached from the internet? Internet-facing moves to the front of the queue regardless of severity score, because exploitation requires no human error.
  2. Is the flaw being exploited in the wild right now? A vulnerability under active attack warrants immediate action, while a theoretical one with no known exploit can wait for your normal cycle.
  3. What does the system hold or connect to? A machine carrying client records ranks above a shared workstation holding nothing.

Severity scores alone are a poor guide. A critical-rated flaw nobody can exploit matters less than a moderate one being used against organizations this week.

The reason given for delay, and its real cost

Organizations postpone updates because an update once broke something important. The concern is legitimate, and the remedy is a staged rollout rather than indefinite deferral — update a small group first, confirm nothing breaks, then proceed.

Indefinite deferral converts a temporary risk into a permanent one. An unpatched system does not become safer as the months pass. Each publicly documented flaw remains open and available to anyone who looks.

A workable cadence for a small organization
  • Automatic updates on every workstation, phone and browser. Enable and leave alone.
  • Router and firewall firmware checked quarterly, since these rarely update themselves and matter most.
  • Website platform and plugins on automatic security updates, with a backup taken beforehand.
  • One hour each quarter to confirm updates are genuinely installing. Machines fail silently far more often than anyone expects.
How serious is this?Serious in one specific place and routine everywhere else. Internet-facing equipment deserves genuine urgency. For workstations, switching on automatic updates and verifying occasionally captures most of the available benefit for almost no effort — and outperforms an ambitious schedule nobody sustains past the first quarter.
?

Employees keep adding browser extensions and connecting apps to our accounts. Is this dangerous?

Where to look first

Open the connected-applications list on your Microsoft 365 or Google Workspace tenant. Most organizations have never viewed it, and most find entries nobody recognizes. Each one represents a third party holding standing permission to read, and sometimes to send.

Review browser extensions separately, since they live on the device rather than in the account. An extension with permission to “read and change all your data on all websites” can observe every page a person opens, including the banking portal.

Why a granted permission outlasts a stolen password
The mechanism worth understanding

When someone connects an application to their work account, they grant it a token rather than a password. The distinction matters considerably.

A token survives a password change, and frequently survives multi-factor authentication as well. Revoking the password does nothing. The connected application continues reading mail and files until somebody explicitly withdraws the grant — which almost nobody thinks to do, because the breach being responded to concerned a password.

How permission gets over-granted

The consent screen arrives mid-task, worded vaguely, while the person is trying to finish something. “Read your contacts” and “Read, compose and send email on your behalf” appear in identical grey text, and nobody reads either. The scheduling tool, the signature generator, the PDF converter, the free analytics dashboard: all legitimate categories, all commonly over-permissioned.

The extension problem specifically

Extensions change ownership. A useful tool acquires a small user base, gets sold, and the new owner pushes an update injecting advertisements or harvesting browsing data. The extension updates silently, and nobody is notified. The product you vetted and the product running today are not necessarily the same software.

What to actually do
  • Review connected applications once, properly, and remove anything unrecognized or unused. Expect the list to be longer than anticipated.
  • Restrict who may grant consent. Both Microsoft 365 and Google Workspace allow administrator approval to be required before staff connect third-party applications. A single setting, and the most effective control available here.
  • Publish a short approved list rather than imposing a ban. Prohibition relocates the activity to personal accounts where you have no visibility at all.
  • Revoke application grants during offboarding, alongside the password reset. Departed staff frequently retain connected applications long after their account closes.
  • Audit annually. Fifteen minutes, and it catches the drift.
How serious is this?Underrated rather than alarming. Few organizations are harmed by a malicious extension, yet connected applications are a standing, invisible grant of access unaffected by the controls most organizations rely on. Requiring administrator approval takes one setting and closes most of the exposure permanently.
?

Our staff work from home, from coffee shops and on personal devices. How do we secure any of this?

Start with the shift in thinking

Stop protecting a location and start protecting the identity. There is no office perimeter to defend when the work happens everywhere, so the account becomes the thing worth securing, not the network someone sits on.

In practice, three measures capture most of the benefit: phishing-resistant multi-factor authentication on every account, full-disk encryption on every device, and a documented way to revoke access remotely when a laptop disappears.

What genuinely matters, and the risk everyone overestimates
Public Wi-Fi is not your problem

Worth stating plainly, because the advice persists well past its expiry. Nearly all web traffic is encrypted in transit now, so the classic coffee-shop interception attack has largely stopped working. A consumer VPN mainly relocates your trust from an internet provider to a VPN company, and the marketing around it considerably outruns the benefit.

A business VPN connecting staff to internal systems is a different matter and remains useful. The two get conflated constantly.

What genuinely creates exposure
  • A stolen or mislaid laptop without encryption. Full-disk encryption is free and built into both Windows and macOS, and it turns a serious data breach into a hardware loss.
  • Passwords reused between work and personal accounts. A breach anywhere becomes a breach everywhere, and remote staff mix the two more readily.
  • Household devices with organizational access. A shared family computer where the browser retains a logged-in session.
  • No means of revoking access. Where a laptop vanishes and nobody can remotely sign that device out, the account remains open indefinitely.
  • Home routers nobody has updated. Running on the firmware shipped four years ago, with the default administrator password still in place.
A proportionate position for a small organization

Require three things of any device touching organizational data: a screen lock, automatic updates enabled, and disk encryption switched on. All three are free, all three are verifiable, and together they address most of what actually goes wrong.

Keep work in the browser where practical. Data accessed through a browser session rather than downloaded locally reduces how much a lost device carries, and revocation becomes a single action in the admin console.

Write down what happens when a device is lost, before one is. Who to telephone, who revokes the sessions, who changes the passwords. Lost devices are discovered at inconvenient hours, which is precisely when nobody improvises well.

How serious is this?Manageable, and frequently over-engineered. Remote work does not demand enterprise tooling for a small organization. Encryption, strong multi-factor authentication and a revocation procedure cover the great majority of realistic scenarios — and are considerably more valuable than the VPN subscription most organizations buy first.
?

I found a USB stick in the car park — or there is a charging cable in the office nobody recognizes. What do I do?

Right now

Dispose of it. Both items. Do not plug either in to identify the owner, not on a spare laptop, and not on a machine you consider unimportant.

If the item appeared somewhere it should not have — inside a locked office, on a reception desk, in a bag — report it before disposing of it. Placement of that kind raises a different question entirely.

The stick is well documented. The cable is the more subtle problem.
The USB stick

Researchers have repeatedly scattered USB drives across car parks and measured how many were subsequently plugged into work machines. The technique continues to succeed, because curiosity is the exploit. Wanting to find the owner is a perfectly decent instinct, and the attack depends on it.

A hostile drive need not behave like a drive at all. Devices exist which are physically identical to a memory stick but identify themselves to the computer as a keyboard, then issue commands faster than anyone could read them. No warning appears, because the machine believes a person is typing.

The cable

Malicious cables are real and sold openly as penetration-testing equipment, with the electronics concealed inside the moulded connector. They are indistinguishable from an ordinary cable by sight or by weight.

We will be straightforward with you, however: we are aware of no documented cases of these being deployed against ordinary consumers. They remain a professional tool, and the odds of the mystery cable in your drawer being one are low.

Why dispose of it regardless

One principle here is worth carrying well beyond this page:

When the safe choice costs you nothing, you need very little evidence to justify it. When the safe choice costs you money or attention, you need a great deal.

Discarding a cable you never owned costs nothing, which is why we offer the advice confidently despite thin evidence. By the same reasoning we tell you not to avoid airport charging points, since avoiding them carries a real cost against a threat nobody has documented.

How serious is this?Barely serious at all, provided you do not plug it in. A near-zero-cost precaution against a low-probability event is the easiest decision available. Reserve your concern for the invoice scenarios above.
Grow

When you are trying to get something moving

The other half of the work. Same format throughout: the first step, the reasoning behind it, and a candid assessment of how difficult it genuinely is.

?

We are a nonprofit. We applied for the Google Ad Grant and were told our website is not up to spec. What now?

Right now

1. Confirm you applied through Goodstack. Google’s validation partner is Goodstack, formerly Percent — not TechSoup, despite a great deal of online guidance still saying otherwise. Beginning elsewhere can stall the entire application on its own.

2. Obtain the specific rejection reason in writing rather than working from a summary. “Not to spec” covers several quite different problems, each with a different remedy.

Their usual objections, and the order in which to address them
Common causes, most frequent first
  • No HTTPS. The site must be secure. This is both the most common objection and the easiest to resolve, since most hosts now include a certificate at no charge.
  • Thin or unclear content. The site must state plainly what the organization does and who it serves. A single holding page with a donate button will generally not pass.
  • Broken links, pages under construction, or placeholder text left in place.
  • Commercial activity reading the wrong way. Advertising on your own site, or affiliate links, can raise questions about the nature of the organization.
  • Domain mismatch. The domain should belong to the organization rather than being a free subdomain on another platform.
The order to work in

Resolve HTTPS first, since nothing else can be assessed without it. Next, make the homepage answer three questions directly: who you are, who you help, and what a visitor should do next. Then reapply.

The part nobody mentions

Approval is the straightforward half. Retention is where charities lose the grant. A 5% click-through minimum, active conversion tracking, no single-word keywords, and an account requiring genuine management. A meaningful proportion of approved organizations lose the grant within a year to rules nobody explained to them.

Before celebrating approval, decide who will run the account. An unmanaged Ad Grant does not sit quietly idle; it gets suspended.

How difficult is this?The website corrections usually amount to a day of work rather than a rebuild. The compliance side is the genuine commitment. Ten thousand US dollars a month justifies the effort — simply go in understanding it as an ongoing responsibility rather than a form submitted once.
?

Everyone keeps telling me to add conversion tracking or “snippets” to my site. Where do I even start?

Right now

Before touching any code, define what counts as success. A booked call, a submitted form, a tapped phone number, a donation. You cannot measure a conversion you have not defined, and most tracking projects fail at this point rather than on anything technical.

Then install a single container rather than five separate snippets. Google Tag Manager places one piece of code on the site and holds everything else inside it.

What these components actually are, and the order to tackle them
Plain meanings

A snippet or tag is a small piece of code supplied by a platform, pasted into your site so the platform can observe what visitors do. A conversion is your instruction to that platform about which action carried value. A container holds all of them, sparing you from pasting code each time.

The sequence
  1. Define the actions worth measuring. Two or three, not fifteen.
  2. Install a tag container once, across the whole site.
  3. Connect analytics so traffic and behaviour become visible at all.
  4. Mark those actions as conversions, then test each one by performing it yourself and confirming it registered.
  5. Only then commit budget to advertising. Advertising without functioning conversion tracking amounts to buying clicks and hoping.
Two problems worth anticipating

Cookie consent. Where you serve visitors in regions with consent requirements, tags must respect the choice a visitor makes. Retrofitting consent afterwards is considerably more painful than planning for it.

Untested tracking. Broken conversion tracking is the most common root cause we find behind “our marketing does not work”. It is worse than having none, since it produces confident numbers which happen to be wrong.

How difficult is this?A competent afternoon for a straightforward site, provided the goals are clear. The technical work is genuinely not the hard part. Deciding what counts as success, then verifying it registers, is where both the value and the failures sit.
?

What is affiliate marketing, and could I sell my products through it for the holiday season?

Right now

In plain terms: you pay other people a commission on sales they send you. They promote, you pay only when a sale completes, and tracking links record who sent what.

An honest answer on timing: with the holiday season only weeks away, this is not your lever. Affiliate programs take months to recruit partners and build trust. Establish one now for next season, and use a faster channel for this one.

What it requires, what it costs, and when it is the wrong choice
What you genuinely need
  • Margin to share. Commission typically runs between 5 and 20 percent. Where your margin cannot absorb this alongside payment fees and shipping, the program loses money on every sale it generates.
  • Tracking you can rely on — a platform or plugin attributing each sale to the correct partner and handling payouts. Most organizations underestimate this component.
  • Clear terms. What partners may and may not claim, whether they can bid on your brand name in advertising, the cookie window, and your payment schedule.
  • Someone to recruit and manage partners. An untended program attracts coupon sites which cannibalize sales you would have made in any case.
Disclosure, which is not optional

Affiliates must clearly disclose when a link is paid. In Canada this falls under the Competition Act’s provisions on misleading representations, and the Competition Bureau has grown increasingly active on undisclosed influencer and affiliate promotion. Enforcement can reach the brand as well as the affiliate, so write disclosure requirements into your terms and verify compliance rather than assuming it.

Where it succeeds, and where it does not

It works well for products carrying healthy margin and clear appeal, in categories with an established audience of reviewers or creators. It works poorly for services, for anything with a long or consultative sales cycle, and for thin-margin goods.

If you need revenue this holiday season, the faster levers are your existing email list, your Google Business Profile, and confirming the checkout genuinely works on a phone. Unglamorous, and they pay this month.

How difficult is this?Setting up a program takes a few weeks. Making it produce meaningful revenue takes a quarter or more of recruitment and relationship work. Treat it as a channel you are building rather than a campaign you are running, and complete the margin arithmetic before anything else.
?

My Google Ad Grant has been suspended. What do I do next?

Right now

1. Do not open a second Google Ads account. This is the most damaging instinct available, and almost everyone has it. Creating a new account to circumvent a suspension is itself a policy violation, and it can convert a fixable problem into a permanent one.

2. Establish which kind of suspension you are facing. Sign in and read the notice at the top of the account. A policy suspension names the rule breached. An inactivity or program-compliance pause is a different matter with a different remedy.

3. Do not reapply or appeal before you have corrected something. A rejected appeal leaves you in a worse position than an unfiled one.

The usual causes, and how each is resolved
Common causes
  • Click-through rate below 5 percent for two consecutive months. The most frequent cause by a considerable margin, and nearly always a symptom of keywords pitched too broadly.
  • Single-word or overly generic keywords. Both are prohibited outright under program policy, and both quietly erode your click-through rate on the way to a suspension.
  • Absent or broken conversion tracking. The program expects at least one meaningful conversion action to be tracked and firing.
  • Missing geographic targeting, or targeting set to the entire world.
  • Account inactivity — no sign-in over an extended period, or the annual program survey left incomplete.
  • Site or advertisement problems — a domain no longer resolving, a site not substantially the organization’s own, deceptive claims, or a mismatch between the advertisement and its landing page.
What to do next

Correct the cause before touching the appeal. Remove the offending keywords, rebuild the ad groups around specific intent phrases, verify conversion tracking is firing, and set your geography properly. Then submit the reactivation request, stating plainly what was wrong and what you changed.

Expect the review to take time. Reviews are not instant, and chasing them does not accelerate the outcome.

Then address why it happened. A suspension nearly always indicates the account was never configured to program rules in the first place. Reinstating it without changing how it is managed buys a few months and no more.

How serious is this?Not very. Most suspensions are recoverable and the grant itself is not lost. The genuine risk lies in the panic response: a duplicate account, or an appeal filed before anything was corrected. Slow down, and this becomes an administrative problem rather than a lost program.
?

We have run this business for 20+ years with no website and done fine. How could one possibly help us now?

The honest answer first

You are right that you did not need one. Twenty years of business built on reputation and word of mouth is a genuine asset, and most companies with handsome websites would trade them for it. Nobody should suggest otherwise, and anyone opening with the implication you have been doing it wrong is selling rather than advising.

What changed is not websites, but what people do before they call you. They look you up first, to confirm you are real, still trading, and the same business someone has just recommended. Where there is nothing to find, a proportion of them stop there. You never hear from those people, which is precisely why the gap stays invisible.

What it genuinely buys you, and what you probably do not need
What a modest site achieves
  • It confirms the referral. Word of mouth still does the selling. A single page simply prevents the handoff failing at the final step.
  • You own it. A social page or directory listing is rented space, where the platform sets the rules, the reach, and whether your page remains available. Your own domain and email cannot be suspended by someone else’s policy change.
  • It answers the questions you field by telephone all day. Hours, service area, the work you do and do not take on, and typical costs. All of it is time returned to you.
  • It is where AI assistants and search engines now read from. People increasingly ask an assistant for a local recommendation, and those answers are assembled from sources the assistant can find. Where nothing about you exists, you are not in contention — not because you lost, but because you were never a candidate.
  • It matters at sale or succession. A business with no findable presence is harder to value and harder to transfer.
What you probably do not need

Not a large build, and not a monthly retainer producing content nobody reads. For a great many established businesses, a properly completed Google Business Profile alongside one honest page — who you are, what you do, where, how to reach you, a few genuine photographs and a handful of real reviews — captures most of the available value. Anyone quoting a substantial project before asking what you actually want more of is guessing.

A poor site is worse than none. A neglected page carrying a dead telephone number, 2019 prices, or a contact form going nowhere actively costs you work. If you will not keep it current, keep it small enough to stay true.

One step worth taking either way

Register your own domain name and move your email onto it, even if the site waits. The annual cost is small, the asset is yours, and it prevents someone else registering your business name later.

Is this urgent?No. You have earned the right not to be rushed. The cost of the gap does compound quietly, however, since it consists of enquiries which never reach you and therefore never appear as a problem you can point to. Treat it as overdue maintenance on an otherwise healthy business rather than an emergency.
The Problem Pool

From what needs attention right now, to what keeps you up at night

Real things people have said to us, close to word for word. Some are emergencies. Most are the quieter kind — a question someone carried around for a year because nobody gave them a straight answer, or one they are living with this week and have not said out loud yet.

Several of these sit across both halves of the job at once, and are labelled Grow + Protect. Those show up under either filter, because the problem genuinely does.

Hit a term you do not know? The glossary explains every word on this site in plain English — written on the assumption that nobody is born knowing this.

“

We never marketed, and we never needed security beyond what Windows gave us. We have been fine so far.

What is usually going on underneath

Start with what is true here, because most of it is. “Fine so far” is real evidence and it deserves respect — you have run a business for years without an incident, which plenty of far better-resourced organisations cannot claim. And Windows Defender is genuinely good now. Anyone who tells you it is worthless is selling something.

The gap is not that you were wrong. It is that “nothing has happened” and “we are not exposed” feel like the same sentence, and they are not. One is a record. The other is a forecast.

What actually changed — and what you probably do not need to do about it
On the security half

What changed is not that threats got cleverer. It is that they got automated and indiscriminate. Most attacks on small organisations are not aimed at you — nobody chose you. Scanners sweep the whole internet for a known weakness and take whatever answers. Being small used to mean being uninteresting. Automation removed that protection, because the cost of trying you fell to nearly nothing.

Defender handles the file-on-the-disk problem well. It does not cover the three things that actually cause bad weeks: someone signing in as you with a working password, a backup nobody tested, and an account you forgot to switch off. Those are not virus problems, so no antivirus was ever going to catch them.

On the marketing half

Word of mouth built this. Keep it — but notice that it is a single channel you do not control, and its capacity is capped by how many people happen to know you. That is concentration risk in commercial clothing. It is the same shape of exposure as one customer being 60% of revenue, and it is fine right up until the week a key referrer retires.

Where we would start — and it is smaller than you expect
  • Multi-factor authentication on email and anything financial. Free, an afternoon, and it removes the single most common way small organisations get hurt.
  • Restore one file from your backup this week. Not review the backup — restore from it. If that fails, nothing else on this list matters yet.
  • List who still has access to what. Former staff, the old bookkeeper, the web person from 2019.
  • Own your domain and your email on it. The commercial equivalent: stop renting your identity.

That is most of the risk, and none of it is a project. If someone is quoting you a monthly retainer before they have asked whether your backup restores, they are selling a product rather than answering your question.

How worried should you be?Not frightened. But “fine so far” stops being evidence the day something happens, and the four items above cost almost nothing against what they cover. Do those and you are ahead of most organisations your size — genuinely, not as a sales line.
“

Our competitors seem to be using new AI tools. We do not want to change. Is it actually necessary?

What is usually going on underneath

Mostly, no — and a great deal of what you are seeing is theatre. Plenty of businesses announce AI adoption and change almost nothing about how they work. Some are worse off, having added a tool nobody governs.

But two real things hide inside the question, and they pull in opposite directions: a genuine efficiency gain on repetitive work, and a visibility shift that is happening whether or not you adopt anything. Those deserve separate answers.

The honest split: what is real, what is hype, and the one risk of standing still
Where it is genuinely useful

Narrow, boring, repetitive text work. First drafts, summarising a long document, turning notes into something sendable, rewriting the same reply for the hundredth time. The gain is real but unglamorous, and it is measured in hours rather than transformation.

Where it is oversold

Anything promising strategy, judgement, or replacing a person who knows your customers. And anything sold as an “AI platform” that is a normal product with a new label on the pricing page.

The one thing standing still does cost you

This is the part that has nothing to do with whether you adopt a tool. People increasingly ask an assistant for a recommendation instead of scrolling a results page, and those answers are assembled from sources the model can find, read and quote. If your business is thinly documented online, you are not losing that comparison — you were never a candidate in it.

So the defensive move is not buying AI. It is making sure clear, accurate, specific information about what you do exists somewhere machine-readable. That is closer to writing a good page than to adopting a platform.

If you do adopt something, the one rule

Decide what must never be pasted in, and say so out loud, before anyone starts. Client records, anything covered by a confidentiality clause, payroll, credentials. The most common AI incident in small organisations is not a rogue model — it is a well-meaning employee pasting something sensitive into a personal account nobody knew existed.

How worried should you be?Not about falling behind on tools — that fear is mostly manufactured, and late adopters of this will be fine. Mildly about being invisible to a question your best customer asks an assistant next year. Those are different problems, and only the second one has a deadline.
“

Someone got into our email — or emails went out pretending to be us.

Right now, in this order

1. Change the password and sign out every session. Changing the password alone is not enough — an attacker with an active session stays in. Look for “sign out everywhere” or “revoke sessions”.

2. Check for mail rules and forwarding you did not create. This is the step people skip, and it is the one that matters most. A rule quietly copying your mail outward, or filing anything containing “invoice” into a folder you never open, means they intended to stay. Remove them and note what they were.

3. Read the Sent and Deleted folders. What went out, and to whom? If anything asked a customer or supplier to change bank details, phone those people now — do not email them.

4. Check the recovery email and phone number on the account. Changing these is usually the first thing done once inside.

Why this one is expensive, and what stops it happening again
What this is called, and why that matters

This is business email compromise, and it costs organisations more than ransomware does. There is no malware to find and nothing looks broken — someone simply signed in as you and read your mail until they understood how your money moves. Then they sent one message, from a real address, at a plausible moment.

That is why it defeats staff training. The email is genuine. It comes from the right person, continues a real thread, and uses the right vocabulary.

Then
  • Turn on multi-factor authentication on every mailbox, not just the owner's. Attackers go for whoever handles invoices, which is rarely the person with the biggest title.
  • Prefer an authenticator app or passkey over text messages. A code by SMS can be defeated by someone taking over your phone number.
  • Set up SPF, DKIM and DMARC on your domain. These are the records that make it hard for anyone to send mail that appears to come from you. Most small businesses have either none or a half-finished set, which is why the spoofing half of this works at all.
  • Agree one out-of-band rule and write it down: no change to bank details is ever actioned on an email alone, no matter who it appears to be from. A phone call to a number you already had defeats nearly every version of this attack.
Also worth doing

Assume anything in that mailbox was read. If it held client records, contracts, or personal information, you may have a notification obligation — that is a question for your lawyer and, if you carry it, your insurer. Tell the insurer early; policies often require prompt notice, and a delay can matter more than the incident.

How worried should you be?Properly worried, and act today. Not because of what was taken, but because access was the goal — the payoff usually comes days or weeks later, in an invoice that looks completely normal. Closing the door is the urgent part; warning the people who transact with you is the close second.
“

We have backups… but we do not actually know if they work.

Right now

Restore something this week. Not check the dashboard, not confirm the green tick — take one real file, or better a database, and bring it back. Time how long it takes and write the number down.

Until you have done that, you do not have a backup. You have a hypothesis. That is not a slogan — a meaningful share of the failed recoveries we hear about involve a backup that had been running, and reporting success, for months.

The four ways backups fail quietly — and what to fix first
How they fail while looking healthy
  • Incomplete scope. It backs up the file server but not the accounting system, the mailboxes, or the line-of-business database that actually runs the company. Very common, and only discovered at the worst moment.
  • Reachable from the network. Ransomware hunts backups first and encrypts them before touching anything you would notice. A backup the attacker can reach is a backup you do not have.
  • Never restored. Corruption accumulates silently. Jobs succeed, files are unreadable.
  • Recovery takes longer than the business can survive. A restore that technically works but needs nine days is a different kind of failure, and it is the one nobody measures until they need it.
Then

Get one copy out of reach. Offline, or immutable — meaning it cannot be altered or deleted for a set period even by someone holding valid credentials. This single property is what makes the difference between a bad week and an existential event.

Answer two questions in plain numbers. How much work can we afford to lose — an hour, a day? And how long can we be down before this becomes serious? Those two answers drive every other decision, and most organisations have never been asked them.

Then test on a schedule and keep the evidence. Quarterly is reasonable for most small organisations. Note what you restored, how long it took, and what broke. That record is also what an insurer or a board will ask for.

One thing people get wrong

Cloud file sync is not a backup. It is a mirror, and it faithfully mirrors encryption and deletion. Versioning and recycle bins help, but they have limits and attackers know exactly what they are.

How worried should you be?This is the single highest-value item on the whole page, and the cheapest to check. An untested backup is the one gap that turns a recoverable incident into a closed business — and you can move it from unknown to known in an afternoon. If you only act on one thing here, make it this.
“

Our employees are using ChatGPT and other AI tools. What are they putting into it?

What is usually going on underneath

The honest answer is that most organisations do not know, and the number using these tools is higher than leadership thinks. This is called shadow AI, and the pattern is consistent: capable people solving real problems with a tool nobody told them not to use.

The exposure is rarely malice. It is a personal account — outside your tenant, outside your logging, with settings and retention you do not control and cannot audit.

What actually gets pasted in, and the fix that does not involve banning it
What tends to go in

Whatever someone was already struggling to write. Contracts being summarised. Client emails being softened. Spreadsheets pasted wholesale to ask what a pattern means. Source code. Draft board papers. Almost always the thing that was hardest to do, which is usually the thing that was most sensitive.

Why banning it fails

A ban moves the activity onto phones and personal laptops, where you have no visibility at all. You trade a manageable problem for an invisible one, and you lose the ability to help people do it safely.

Where we would start
  • Name two or three approved tools. Not a policy document — a short list people can actually remember. Ambiguity is what pushes people to personal accounts.
  • Provide business accounts for those tools. The paid or tenant-linked versions generally give you administrative control and clearer data handling than a personal sign-up. This is the highest-value single step, and it is a purchase rather than a project.
  • Write down what must never be pasted in. Client or patient records, anything under a confidentiality clause, credentials, payroll, unreleased financials. One page. Specific, not abstract.
  • Say what output must be checked before it leaves the building. Anything going to a customer, a regulator or a board.
  • Ask, without blame, what people are already using. You will learn more in one honest conversation than from any technical control, and you cannot govern what you have not been told about.
The part that catches people out

AI features are arriving switched on inside tools you already pay for — note-takers joining meetings, assistants summarising mailboxes, features added in an update nobody read. So “we do not use AI” is frequently untrue by the time it is said. Worth checking what is enabled by default across your existing subscriptions.

How worried should you be?Concerned enough to act this quarter, not alarmed. Nothing here is catastrophic on its own, and the fix is unusually cheap — an approved list and one page of rules removes most of the exposure. The genuine risk is leaving it unaddressed long enough that something confidential ends up somewhere you cannot account for to a client who asks.
“

We are paying for marketing, but I have no idea what is actually working.

What is usually going on underneath

This is almost never a marketing problem. It is a measurement problem, and it is the single most common thing we are asked about on the Grow side.

In most cases one of three things is true: conversion tracking was never installed correctly, enquiries arrive by routes nobody counts — phone calls, walk-ins, replies to a personal inbox — or the numbers exist but sit in four dashboards that disagree with each other. You are not failing to read the data. There is no single version of it to read.

How to get to an answer you can trust, in about three weeks
Start at the end, not the beginning

Define one thing that counts as a win — a booked call, a submitted form, a completed sale. Then check it is actually being recorded. Broken or missing conversion tracking is so common that we treat it as the default assumption until proven otherwise, and until it is fixed every other number on this list is decoration.

Then close the counting gaps
  • Ask every new enquiry how they found you and write it down for eight weeks. Crude, unfashionable, and frequently more accurate than the analytics.
  • Tag your links so email, social and ads stop collecting in a bucket labelled “direct”.
  • Route enquiries to one place. If some arrive in a personal inbox, they are invisible by definition.
  • Accept that attribution is approximate. Every model is a simplification and they disagree. Pick one, learn its bias, and stop switching — comparing across models is how people conclude that nothing works.
What good looks like

Not a dashboard with forty numbers. Three numbers you trust: how many enquiries arrived, where they came from, and what a customer costs you to acquire. Most organisations we meet cannot answer the third, which is the one that decides whether any of the spending is sensible.

An honest warning

Once this is measured properly, you will probably discover that something you have been paying for monthly is producing very little. That is the point, and it is usually uncomfortable — often the thing that looks busiest is the thing contributing least.

How urgent is this?Not an emergency, but every month unmeasured is a month of spending on faith. The fix is small and mostly one-off — and it is the prerequisite for every other Grow decision, so doing it first makes everything after it cheaper.
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Our board, our insurer or a client is asking what cybersecurity measures we have. What do we say?

What is usually going on underneath

The question is almost never really about technology. It is about whether anyone is accountable. A board asking this is asking whether someone owns the risk. An insurer is asking whether you qualify for the price they quoted. A client is asking whether you are a safe link in their own supply chain.

Those three want different evidence, and the most common mistake is answering with a list of products. “We have antivirus and a firewall” reads, to all three audiences, as though nobody is in charge.

What to put in writing — and the one answer that is worse than "we do not know"
Answer in four parts, on one page
  • Who is accountable. A named person, even if the work is outsourced. Outsourcing the work does not outsource the accountability, and every one of these audiences knows that.
  • What you actually have in place. Multi-factor authentication and where it is enforced; how devices are patched; what is backed up and when it was last restored; who has administrative rights; how leavers are removed.
  • What happens when something goes wrong. Who is called, in what order, and who can authorise spending at 11pm on a Saturday. This is the part that most distinguishes a serious answer from a nervous one.
  • What you know you have not done yet, and when you will. Counter-intuitive, but a short honest gap list with dates reads as competence. A flawless claim invites someone to go looking.
Insurers specifically

Treat the application as a technical questionnaire with contractual weight, because that is what it is. Questions about multi-factor authentication, backups, endpoint protection and patching are conditions, not curiosity. Answering optimistically is the genuinely dangerous move — a claim can be challenged on the basis of what you attested to. If you are not certain, verify before you tick.

Clients and procurement

Expect a questionnaire that was written for a company twenty times your size. It is reasonable to answer “not applicable at our scale, and here is what we do instead”. Do not invent a policy to fill a box. If you claim one, you may be asked to produce it and to show it is followed.

Where we would start if you have nothing written down

One page covering the four points above. That page is worth more than any tool purchase, because it is what turns scattered good practice into something you can show. Being able to evidence what you do is now part of doing it.

How worried should you be?Not worried, but do not stall — silence reads badly to all three audiences, and to a board it reads as nobody being in charge. This is a writing task more than a technical one, and most organisations discover they are doing more than they could prove. Just never overstate it in a document that could be tested later.

What happened to you?

This page grows from real situations, not from a list we invented. If something happened to you and it is not here, tell us — anonymised, no detail we would ever publish, and we will write it up so the next person finds an answer instead of a panic.

Already in the middle of it?

If money is moving right now, stop reading and phone your bank — use the word fraud. Then report it to the Canadian Anti-Fraud Centre. Speed matters more than getting the sequence perfect.

If something here resonated

Several of these are questions people carried around for months without getting a straight answer. If one of them is yours, book a free conversation or just email the question. No pitch, no obligation.

And we will tell you if you do not need us. Some of what is on this page you can do yourself in an afternoon, and we would rather say so than sell you something.

Educational only. Everything on this page reflects our own experience and published research, offered as a starting point for your own independent research — not as advice about your circumstances, your systems, your contracts or your legal obligations. Verify anything consequential, seek qualified professional help where money, data, staff or regulators are involved, and proceed at your own risk. Responsibility for what you do with this stays with you.

Our full methodology and limitations statement explains how we reach the positions we take, including where we are relying on judgement rather than evidence.