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+# SuperOffice Email Sending Strategy Analysis (Feb 28, 2026)
+
+## Executive Summary
+Automated email sending "on behalf of" sales representatives directly via the SuperOffice API is currently **technically blocked** due to missing permissions and license restrictions on the configured System User (Client ID `0fd8...`).
+
+We have exhausted all standard API paths (Agents, REST, Archive, CRMScript). A strategic reconfiguration by the SuperOffice administrator is required.
+
+## Technical Findings
+
+| Feature | Status | Error Code | Root Cause Analysis |
+| :--- | :--- | :--- | :--- |
+| **Document Creation** | ✅ Working | 200 OK | We can create `.somail` files in the archive. |
+| **Native Sending** (`/Shipment`) | ❌ Failed | 500 Internal | The System User lacks a valid `Associate` context or "Mailing" license. |
+| **Agent Sending** (`/Agents/EMail`) | ❌ Failed | 401 Unauth | The standard OAuth token is rejected for this Agent; likely requires "interactive" user context or specific scope. |
+| **CRMScripting** | ❌ Failed | 403 Forbidden | Access to the Scripting Engine is blocked for this API user. |
+| **User Context** (`/Associate/Me`) | ❌ Failed | 500 Internal | **Critical:** The System User does not know "who it is". This breaks all "Send As" logic. |
+
+## Required Actions (IT / Admin)
+
+To enable automated sending, one of the following two paths must be implemented:
+
+### Option A: Enable Native SuperOffice Sending (Preferred)
+1.  **Fix System User:** The API User must be linked to a valid "Person" card in SuperOffice Admin with **Service / Marketing Administrator** rights.
+2.  **Enable Mailings:** The tenant `Cust26720` must have the "Marketing" license active and assigned to the API User.
+3.  **Approve "Send As":** The API User needs explicit permission to set the `SenderEmailAddress` field in Shipments.
+
+### Option B: External Sending Engine (Recommended Fallback)
+If Option A is too complex or costly (licensing), we switch the architecture:
+1.  **SMTP Relay:** Provision a dedicated SMTP account (e.g., Office365 Service Account or SendGrid) for the "RoboPlanet GTM Engine".
+2.  **Logic Shift:** The Python Connector sends the email via SMTP (Python `smtplib`).
+3.  **Archiving:** The Connector saves the *sent* email as a `.eml` document in SuperOffice (which already works!).
+
+## Immediate Workaround
+Until a decision is made, the system uses the **"Activity Handoff"** method:
+1.  System generates the text.
+2.  System creates a Task (Appointment) in SuperOffice.
+3.  User clicks a link, copies the text, and sends via their own Outlook/Gmail.