Sending, receiving, and organizing email in Outlook.com
Hello Shane,
Thank you for posting your question in the Microsoft Q&A Forum. I understand that you are experiencing email bounce-back whenever you send emails, and I’m sorry for the inconvenience. Could you confirm whether the bounced email included any PDF attachments?
If your email contained PDF attachments, please check this article for a workaround option: Unable to attach files in Outlook.com.
Otherwise, you can try adjusting Settings (gear icon) > Search for "Compose and reply" in search box > Change Message format from Compose messages in HTML to Plain text format in your settings to see if that resolves the issue.
Regarding the email account that cannot log in, could you provide the exact message Microsoft displays when you attempt to sign in? (Please remove any personal information before sharing.) This will help me guide you more effectively.
Thank you so much. If you still need assistance, please click “Add Comment” to follow up with me.
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Best regards.