November 4: How To Automate Security Documentation

The best way to create a good habit is to automate it so you never have to think about it again.

James Clear, Atomic Habits

In my work helping clients secure their Microsoft cloud services, I learn something new almost every day. Undocumented quirks, easy-to-make mistakes, and hard-earned best practices rattle around my head like so many loose screws in a toolbox — screws I carefully select when crafting each deliverable.

To reduce friction and improve consistency, I figured automation could help me produce better deliverables with less effort.

Not every client needs every topic covered. So I built a SharePoint list with Boolean checkboxes for 34 security configuration topics across Azure, Intune, Entra, Purview, and Office 365. I then built a Power Automate Flow that triggers whenever a list item is created or modified, assembling the relevant topic documents into a personalized client deliverable.

Some security configurations are client-specific, so I allow topic documents to be overridden with customized versions found in dedicated client folders.

This system helps me deliver greater value while giving my best practices a more permanent home. Feel free to reach out if you want a closer look!

After working through some quirks in SharePoint list item parsing and content encoding, the final Power Automate flow:

  • Triggers when a list item is created or updated.
  • Retrieves which content flags are enabled.
  • Loads the corresponding Word documents from SharePoint folders.
  • Merges them using Encodian’s Word – Merge Files action.
  • Outputs a client deliverable ready for review.