Thanks for the update. Can you send emails to other accounts? In the end, this is a rejection from the recipient's system, and after multiple emails, the recipient detected them as spam.
Delivery has failed to these recipients or groups
I keep getting the message below, despite changing the text / content to sound less like spam:
This has now happened for 2 different contacts.
I am using hotmail / outlook on Chrome.
Delivery has failed to these recipients or groups:
[person's email address]
Your message wasn't delivered because the recipient's email provider rejected it.
Diagnostic information for administrators:
Generating server: AS4PR08MB7759.eurprd08.prod.outlook.com
[person's email address] Remote server returned '554 5.7.0 < #5.7.520 smtp;550 5.7.520 Message blocked because it contains content identified as spam. AS(4810)>' Diagnostic information for administrators:
Generating server: DB9PR08MB8674.eurprd08.prod.outlook.com
[person's email address] Remote server returned '554 5.7.0 < #5.7.520 smtp;550 5.7.520 Message blocked because it contains content identified as spam. AS(4810)>'
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Emmanuel Santana 38,255 Reputation points Independent Advisor2026-04-09T09:04:57.1366667+00:00