Session Overview

Sam requested a comprehensive cleanup and organization of his personal Mac files across three folders: Desktop, Documents, and Downloads. The goal was to visually examine every screenshot, rename files descriptively, group them into logical folders, delete junk, remove duplicates, and reclaim disk space. Total space recovered so far: approximately 22.3 GB.

Desktop and Documents work is complete. Downloads Phase 1 (large files, installers, video duplicates) is complete. Downloads Phase 2 (empty folders, duplicate zips, duplicate docs, loose file organization) was approved but not yet executed.

What Was Accomplished

Desktop (Complete)

83 loose screenshots (Dec 13, 2025 to Feb 7, 2026) were visually examined, renamed descriptively, and sorted into 7 folders: Marketing-Video-Stills (11), Marketing-Stock-Photos (26), Website-QA (13), Google-Ads (3), Development (3), Security-Camera (4), Misc-Reference (6). 17 junk files deleted. Zero loose screenshots remaining. Six .mov screen recordings and one .zip left in place.

Documents (Complete)

Started at 1.7 GB, 28,610 files. Deleted wp-content backup (28,225 files, ~1.6 GB), metasync.log (182 MB), duplicate CSV (13.3 MB). Organized 157 loose root files into Review/ folder with 8 subfolders: Data-Exports (55), Blog-Images (55), Team-Headshots (11), Photos (22), Design-Assets (4), Potential-Duplicates (5), Needs-Renaming (empty), Misc (10).

Downloads Phase 1 (Complete)

Started at 48 GB. Freed ~21.9 GB: deleted 24 installers (CapCut x4, Microsoft Office, Genetec, VS Code, Claude x2, ChatGPT x3, Screaming Frog, etc.), Singleton video duplicates (6.3 GB), and IMG_2329 duplicate MOV (370 MB).

Downloads Phase 2 (Approved, NOT Executed)

Four tasks approved but not started:

  1. Delete 73 empty folders (exclude sam-wp)
  2. Delete duplicate zips (~575 MB): Photos-1-001 (2)(3)(4), Google Ads Assets (1), How to Improve FAQ Page (1)(2)(3) + unzipped folder, 3-21-cv-00478-DJH (1)(2), 3-21-cv-00135-CRS-RSE (1)(2)(3), Reducing Cannibalization (1)(2), PIM Presentation (1)
  3. Delete duplicate documents (~15 MB): Brand Guidelines, RandyCook cover letters, Decline Letters, SAIL spreadsheets, Schema files, Presentation Prompts, NSC docs, FAQ schema files. Keep highest-numbered version.
  4. Organize ~30 loose root files into existing subfolders

Technical Issues and Workarounds

Unicode U+202F: macOS Sequoia uses narrow no-break space before AM/PM in screenshot filenames. Bash mv commands fail. Solution: use Python with .replace('\u202f', ' ') for all file operations.

Delete permissions: allow_cowork_file_delete must be called before deletions. Even after calling it, Desktop deletions initially failed; workaround was moving to To-Delete/ folder. Documents deletions worked after second permission grant.

Downloads mount: Does not persist between sessions. Must re-request via request_cowork_directory. First mount attempt may return empty; retry fixes it.