Using Classic Outlook on Windows for personal email, calendar, and contact management
Hi Randy Bauld
I understand how frustrating this must be, especially since emails from this sender were delivered successfully until July 29, 2026, and you have already added both the individual address and the sio.midco.net domain to your Safe Senders list.
Since you can send messages to this person and receive their replies, but newly composed messages from that specific account do not arrive, please first search for the sender’s full email address in Outlook.com and select All folders. Also check Junk Email, Deleted Items, Archive, and the Other tab if Focused Inbox is enabled.
Next, go to Settings > Mail > Rules and make sure no rule is moving or deleting messages from this sender. Please also check whether a Sweep action was previously applied. Under Settings > Mail > Junk email, confirm that neither the sender’s address nor the sio.midco.net domain appears in the Blocked senders and domains list.
If the messages are not in any folder, please ask the sender’s email administrator to check the delivery log for a recent test message and provide the final SMTP response from Microsoft, along with the date and time sent, message ID, and any rejection or delayed-delivery notice. A record showing only that the email left their server does not confirm that Outlook.com accepted it.
If the log shows that Microsoft rejected or delayed the message, the sender’s administrator will need to investigate the sending server’s configuration and reputation and contact Microsoft Support if necessary.
Please note that this is a user-to-user support forum. Moderators, contributors including external Microsoft employees cannot directly intervene in Microsoft product features or access back-end systems. Our role is limited to providing technical guidance on reported issues, requests, or ideas only.
I hope this helps identify whether the message is being redirected inside the mailbox or stopped during delivery. Please feel free to let us know what the sender’s administrator finds.
Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.