Documents Folder Cleanup — Full Execution + Verification — 2026-05-20

Session Overview

This session started as a request to build a top-level index of the entire /Users/samaguiar/Documents folder (33 top-level folders, ~95k files total) so Sam could identify consolidation opportunities. After reviewing the index, Sam approved executing all three cleanup tiers (A, B, C) plus full autonomous cleanup of all 40 loose root files. The session ended with full execution, verification, and workbook update.

The planning Notion entry (index creation only) is at: Documents Folder Index + Consolidation Plan — 2026-05-20

This entry covers the execution phase.

What Was Accomplished

Index Workbook

Created /Users/samaguiar/Documents/Documents-Folder-Index-2026-05-20.xlsx via Python/openpyxl with 5 tabs:

Overview: 33 top-level folders with flags and last-mod dates
Root Files: 40 loose files with suggested destinations
Consolidation Plan: 13 ranked P1/P2/P3 opportunities
Folder Map: Second-level expansion of Projects, Claude, Codex, etc.
Cleanup Done (added at session end): Full execution summary with before/after, every move, every deletion, and final root state

Rollback Manifest

Created /Users/samaguiar/Documents/ROLLBACK-MANIFEST-2026-05-20.md before any moves. Every file operation is logged with its inverse mv command. Safe to archive after 30 days.

Before vs After

Metric	Before	After
Root-level items	73 (33 folders + 40 loose files)	12 (10 folders + 2 files)
Loose files at root	40	2 (index.xlsx + rollback manifest)
Named top-level folders	33	10
Empty folders deleted	0	10+
Folders archived	0	2

Phase A: Critical Moves (P1)

8 UPS/Boeing case PDFs moved from root to UPS-Case_project/04 - Evidence and Exhibits/
Prehearing Statement (Sam).pdf moved to Laduke/