Modern phishing emails arrive as convincing invoices from vendors you actually use, fake Microsoft 365 login pages, and urgent messages appearing to come from your own boss. This post covers the five types of phishing hitting Calgary businesses in 2026, five habits that catch most attempts, and an exact five-step response protocol for when someone on your team clicks something they should not have.
Windows 10 reached end of support in October 2025, meaning Microsoft stopped releasing security patches. Attackers are already targeting businesses running Windows 10 knowing unpatched systems cannot defend against the latest phishing and malware techniques. Calgary small businesses still running Windows 10 face compounding risk from an ageing operating system and increasingly sophisticated phishing campaigns.
Break-fix IT works fine for small, simple setups — but there is a tipping point. When IT problems start costing more than repair bills, when updates happen only when someone remembers, and when security scares go unaddressed, the reactive model is no longer adequate. This post identifies five specific signs Calgary small businesses have already crossed that line and explains what a managed IT alternative actually looks like.