Why does my network scanner keep failing when trying to send multi-page PDF documents directly to my Microsoft 365 email via SMTP and how do I fix the authentication error
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Fan-out diagram
The searches the AI actually ran for this prompt.
SEED QUERY
Why does my network scanner keep failing when trying to send multi-page PDF documents directly to my Microsoft 365 email via SMTP and how do I fix the authentication error
2 real searches · 1 real-search pass
Badge and edge weight = share of passes that produced the query. Hover a query for its intent and routing format.
Query classes
Google's semantic query class for every sub-query: what kind of answer each search is after, simulated vs real.
ChatGPT real searches (2)
Classes come from the query-classifier (a local Laya model). 2 of 2 calls are low-confidence (under 50%) — hover a query in the table to see its confidence.
Searches and sources
ChatGPT2 real searches · gpt-6
Microsoft 365 SMTP AUTH client submission settings smtp.office365.com port 587 STARTTLS authentication basic authentication retirement 2026 Google ↗
Microsoft 365 enable or disable SMTP AUTH per mailbox Exchange Online documentation Google ↗
- How to set up a multifunction device or application to send email using Microsoft 365 or Office 365 · learn.microsoft.com
- How to set up a multifunction device or application to send email using Microsoft 365 or Office 365 · learn.microsoft.com
- Microsoft 365 Admin Center · admin.microsoft.com
- Enable or disable SMTP AUTH in Exchange Online · learn.microsoft.com
- Exchange Admin Center · admin.exchange.microsoft.com
- Updated Exchange Online SMTP AUTH Basic Authentication Deprecation Timeline · techcommunity.microsoft.com
- Deprecation of Basic authentication in Exchange Online · learn.microsoft.com
Queries
2 queries · click a column to sort
| Query / type | Search | Intent | Query class | Routing format | Cluster | Freq ↓ | Weight |
|---|---|---|---|---|---|---|---|
Microsoft 365 SMTP AUTH client submission settings smtp.office365.com port 587 STARTTLS authentication basic authentication retirement 2026 OBSERVED | Google ↗ AI Mode ↗ | — | Instruction | — | — | 1x of 1 | |
Microsoft 365 enable or disable SMTP AUTH per mailbox Exchange Online documentation OBSERVED | Google ↗ AI Mode ↗ | — | Instruction | — | — | 1x of 1 |