Is Your Business Leaking Data Without You Knowing?

Posted: February 27, 2026

Asked where we actually see data leave a business, the honest answer is email, email, and email. Not sophisticated intrusions. Someone sends something, forwards something, or has their mailbox read by someone who should not be in it.

The other routes matter. They are a long way behind the first one.

Email, Three Ways

Mailboxes being read. A compromised account is a quiet, continuous leak. The attacker is not stealing files, they are reading correspondence, and most businesses have no way of knowing it is happening.

Forwarding rules. A rule that copies messages to an outside address, created by an attacker or occasionally by a departing employee. It keeps working long after any password change. Almost nobody audits these.

Ordinary mistakes at volume. Autocomplete selecting the wrong recipient. A spreadsheet attached with more tabs than intended. A reply-all on a confidential thread. Individually trivial, collectively the most frequent cause of reportable incidents.

For the mailbox compromise route specifically, our post on business email compromise covers how attackers get in and stay in.

The Other Routes

Departing staff. Accounts left active after someone leaves is one of the most common findings when we assess a new client's environment. Add personal devices still synced to company file shares, and credentials to shared accounts that nobody changes.

Personal cloud storage. Someone moves a file to a personal account to work on it at home, and it stays there. Not malicious, entirely invisible, and completely outside your control.

Unmanaged devices. A personal laptop with company data on it cannot be wiped, audited or recovered when the relationship ends.

Why It Stays Hidden

A leak produces no symptom. Nothing breaks. Nobody is locked out.

Unless something is specifically watching for the behaviour, the business finds out from a customer, a supplier, or a regulator. Usually long after it would have been cheap to fix.

What to Check This Week

  • Audit mailbox forwarding rules across every account. This takes a few minutes and finds things more often than people expect.
  • List everyone who has left in the past year and confirm their access is genuinely closed.
  • Ask whether anyone works on company files from a personal device or a personal cloud account.
  • Find out whether anything is monitoring for unusual mailbox activity. If the answer is no, that is the gap.

If you hold personal information about customers or staff, a leak carries obligations under PIPEDA as well as commercial consequences. The Office of the Privacy Commissioner sets out what is required.

How Digital Sky Solutions Helps

At Digital Sky Solutions, we help small and mid-sized businesses across Victoria and Vancouver understand where their data lives, how it moves, and where the real risks are.

Our work often includes:

  • Reviewing data access and permissions
  • Securing devices, email, and cloud platforms
  • Implementing encryption and monitoring
  • Providing employee security awareness training
  • Delivering ongoing managed IT and cybersecurity support

If you are unsure whether your business is leaking data, or you want a clearer picture of your current risk, we can help you get answers and put practical protections in place. Learn more about our Cyber Security Services here. Call us at (250) 483-5623 or send us a message to start a conversation.

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author avatar
Carlos Flores Founder and President
Carlos Flores is the founder and President of Digital Sky Solutions, a BC-based Managed IT Services Provider (MSP) he launched in 2006 to help businesses harness technology for long-term success. With nearly two decades of leadership in the Managed IT industry, Carlos works closely with clients, employees, and partners to deliver world-class IT service and support. He’s dedicated to staying ahead of technology trends, security best practices, and evolving cybersecurity threats—ensuring clients have the tools, protection, and strategies they need to thrive in a fast-changing digital landscape. His focus is on creating scalable, repeatable technology roadmaps that keep systems secure, efficient, and ready for growth.

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