Outlook emails landing in recipients' Spam/Junk folder

Hello Stefan Vlajich,

Thank you for providing those details. Since you're using an Outlook.com account and the issue mainly affects recipients who have not previously contacted you, I'd like to gather a bit more information while we perform a few quick checks.

Could you please confirm:

• Do messages sent from Outlook.com on the web also go to recipients' Junk folder, or only messages sent from the Outlook app on your Mac?
• Does this happen with all recipients or only certain domains (for example Gmail, Outlook.com, company email addresses, etc.)?
• Have any recipients marked your messages as "Not Junk" and then successfully received future emails in their Inbox?

As a first test, please try the following:

• Sign in to Outlook on the web at Outlook.com.
• Send a simple plain-text test email (no links, images, attachments, or special formatting) to a recipient who has experienced the issue.
• Ask the recipient whether the message arrives in their Inbox or Junk folder.
• If it still goes to Junk, ask the recipient to mark the message as "Not Junk" and then send a second test message to see whether delivery improves.

For reference, Microsoft notes that junk mail filtering can be influenced by recipient-side filtering and sender reputation, and that marking messages as "Not Junk" helps improve future delivery decisions:

• Mail goes to the Junk folder by mistake
• Filter junk email and spam in Outlook

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