PipedreamHQ / PipedreamHQ/pipedream

Microsoft Outlook / Microsoft Graph

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bug triaged user request
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Description

### App
Microsoft Outlook / Microsoft Graph

### Summary:
Exchange rejects Pipedream Connect Graph sends with 550 5.7.501 while Outlook Web sends succeed

### Details:
We are using Pipedream Connect's proxy to call Microsoft Graph v1.0 for a delegated Exchange Online mailbox. We create a new or reply draft, update its recipients/body, optionally attach a small file, and call POST /me/messages/{id}/send.

Graph accepts the calls, the message appears in the correct mailbox's Sent Items, and Exchange message trace shows Received -> Processed -> Not delivered. Exchange then generates an NDR for both same-tenant and external recipients:

550 5.7.501 Service unavailable. Spam abuse detected from IP range.
Marker: S(2017052602)

Tenant: ralfiio.onmicrosoft.com
Test sender: ralfi-test-03@ralfiio.onmicrosoft.com
External test recipient: tarzanclawsonmain@agentmail.to

Controlled results on 15 July 2026 (Australia/Sydney):
- Outlook Web: Test 03 -> same-tenant Test 01 delivered.
- Outlook Web: Test 03 -> external AgentMail delivered.
- Outlook Web: Test 01 and Test 02 controls delivered.
- Pipedream Connect / Graph exact reply with attachment: all recipients failed. MessageTrace ID 6b9852c1-dbcd-4f0a-d254-08dee2384f89.
- Same Graph reply with no attachment: all recipients failed. MessageTrace ID dc0922d9-de20-4e97-2724-08dee23d9b44.
- New Graph message, one external recipient, plain text, no attachment: failed. MessageTrace ID 88e2e830-9166-4194-acc0-08dee240ff31.

The traces report source IPs 20.190.151.37 and 20.190.152.152. Microsoft Defender Restricted entities contains zero users/connectors. Exchange has zero transport rules and zero connectors; forwarding is off.

This isolates the failure to the Pipedream Connect / Microsoft Graph path rather than the mailbox, recipients, attachment, message body, or tenant-wide outbound delivery.

Could you please:
1. Confirm whether there is a known Microsoft anti-abuse or reputation issue affecting Pipedream's managed Microsoft OAuth client or Connect proxy path.
2. Identify whether Microsoft could be associating these sends with a Pipedream application identity or shared service path.
3. Advise whether we should use a custom Microsoft OAuth client to bypass the managed client, or whether Pipedream can escalate/delist the affected path with Microsoft.

Please tell us what additional non-secret identifiers or trace evidence you need. We can provide the full sanitized NDR and Exchange event details.

### Screenshots:
No screenshots included

Contributor guide

Open the contributing guide

Research direction

No repository file, test, or entry point is named. Start by locating the Pipedream Connect Microsoft Graph OAuth/proxy path, then compare its sends with the supplied Exchange message traces; done means determining whether the managed path is responsible and documenting the escalation or supported workaround.

Written by the indexing model from the issue text.

Assessment

Domain
api
Issue type
Bug
Difficulty
5/5
Estimated time
Over a week
Activity status
Quiet
Clarity
Needs clarification
Newbie friendliness
35/100

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