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Security writing for practitioners

Analysis and field notes from working with small businesses and MSPs on security, documentation, and compliance.

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Security Operations8 min read

Why Solo MSPs Need Documented Environments Before They Need Monitoring

It's 2am. A client site goes down. Your monitoring tool fires an alert. But now what? The firewall credentials are in someone's head, or an old spreadsheet, or a sticky note in an office you can't get into until 8am. This is not a monitoring failure. What failed was everything that comes before monitoring: knowing the environment.

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Compliance9 min read

How Small Law Firms Are Answering Insurer Security Questionnaires in 2026

The renewal questionnaire arrives. It's longer than last year. It asks for MFA enforcement logs, immutable backup configuration, and evidence your incident response plan was tested in the last twelve months. You have most of these controls. You just can't prove it. And in 2026, "we have it" isn't the answer carriers want.

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Phishing10 min read

Three Months of Phishing Simulation Data from SMB Engagements

Here's what we found running phishing simulations across 12 SMB clients over a 90-day period: the first simulation is almost never the interesting part. The interesting part is what happens after it. Click rates, report rates, who clicked twice — that's the data that tells you whether the program is working.

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