Operator profile

Hi, I’m Sky
Blu DeGrate.

IT support. Cybersecurity. Still asking why the computer did that.

I’m an IT support professional based in Brooklyn, New York, with more than five years of experience helping people troubleshoot hardware, software, accounts and connectivity. My background includes Windows and macOS support, Microsoft 365 and Google Workspace, account access, MFA, onboarding and documentation. I earned CompTIA Security+ in February 2026.

I’m documenting my path into cybersecurity: the labs I build, the attacks I study, the tools I misuse before learning to use them correctly, and the moments AI says something with terrifying confidence that turns out to be completely false.

This site is part technical portfolio, part field journal, and part evidence that persistence occasionally defeats configuration files.

The work behind the case files

These are personal labs and training investigations. I build the environment, follow the evidence, write down what broke, and distinguish what I observed from what I only expected to happen.

• Wazuh + Sysmon endpoint detection

  Getting a Windows endpoint talking to an Ubuntu-hosted manager, fixing enrollment, and validating a custom detection rule.

• Windows incident investigation

  Connecting process, file, DNS, network and registry events into a timeline, then working out why collected events did not all become alerts.

• Linux forensics with LuckyShot

  Reconstructing a Hack The Box training incident through authentication logs, shell history and persistence artifacts. Configured, attempted and observed are different findings.

There’s a creative side, too.

My background includes Screen Studies at The New School and software-development training at Flatiron School. Film, storytelling and building things for the web are part of how I approach technical work: notice the details, understand the sequence, and explain what happened clearly.

The name here is Documentation Princess. The person behind it is Sky Blu DeGrate.