Date: 2026-05-25. Type: Workflow. Project: Operations. Status: Complete. Priority: High.

1. Session Overview

Sam Outlook 365 mailbox hit storage cap. New mail blocked. Goal: free space fast. Two firm priorities up front: empty Junk Email, empty Deleted Items. Then find other big storage hogs and report; no deletion without approval.

Goal evolved mid-session. After report delivered, Sam approved deleting everything dated before 2025-11-01 across the recommended hog folders. Did that too. End goal now broader: keep mailbox leaner + more organized.

2. What Was Accomplished

Connected to mailbox via MS Graph API, client-credentials OAuth flow. App = "Sam Outlook Knowledge Review". Browser (outlook.office.com via Chrome MCP) used for folder Empty actions; Graph API used for everything else.

Step 1 - Junk Email: emptied via browser right-click Empty. 10 items gone.

Step 2 - Deleted Items: emptied via browser. 5,011 items, ~1,062 MB gone.

Step 3 - storage audit via Graph: pulled all folder sizes + item counts. Found big hogs. Reported to Sam, no deletion.

Step 4 - after Sam approval, purged all items dated before 2025-11-01 from: Sent Items, CallRail Calls, Alert Call Center, SpeedAI, Dashboards from Nate, KJA Listserve, NSL - Derby City Squash. Clutter already auto-cleared by Outlook 30-day rule. ~31,400 messages deleted total. ~6 GB freed.

Method: Python script. Graph $batch endpoint, DELETE 20 messages per request. Filter receivedDateTime lt 2025-11-01 (or sentDateTime for Sent Items). Paginate IDs 100 per page, then batch-delete.

3. What Was Tried and Didn't Work

• First script version: token expired mid-run (1 hr TTL). Long folders -> many batches failed 401. Reported high "failed" counts (e.g. CallRail 4,073 failed first pass).
• Fix: rewrote script with proactive token refresh every 30 min plus per-batch 401 retry. Re-ran. Still some failures per pass.
• Root cause of "failures": mostly cosmetic. Folder counts confirmed deletes succeeded far beyond what script self-reported. Took 3 to 4 cleanup passes per big folder to hit zero pre-Nov-2025 remaining. Verified via Graph $count with ConsistencyLevel: eventual header.
• Graph folder query with $select failed 400 when $ mishandled in shell. Workaround: drop $select, run query in Python heredoc.
• Graph $orderby=size plus $filter=hasAttachments on messages: 400 InefficientFilter. Workaround: used $search KQL (size>10000000) to find big mail.

4. Decisions Made and Reasoning

• Browser for Empty folder, Graph API for bulk date-filtered deletes. Browser has one-click empty; API has no empty-folder endpoint but does precise date filtering.
• Skipped Drafts. Drafts can hold unsent demand letters or work product. Needs separate approval.