This typically happen because of a rule, filter, sweep setting, blocked sender configuration, mailbox cleanup setting, or a connected device/app that is deleting them automatically.
First check for inbox rules. Go to Settings > Mail > Rules and look for any rule that moves or deletes messages. Disable or remove suspicious rules, especially ones using conditions like specific senders, keywords, or “move to Deleted Items.”
Next, check Sweep settings if you use Outlook.com. Open the message from a sender being affected, select Sweep, and verify there is no cleanup rule configured to move or delete future messages automatically.
Also review blocked senders and junk filtering. Go to Settings > Mail > Junk email and make sure the sender or domain is not listed under Blocked senders and domains. Sometimes messages are routed incorrectly and then deleted by another rule.
If you use the Outlook desktop app alongside webmail, check desktop rules too. In Outlook desktop, go to File > Manage Rules & Alerts and review all active rules. Rules created in the desktop app can still affect messages on the server.
Another potential cause is mobile mail apps or third-party email clients. If your account is connected to an iPhone Mail app, Android mail app, Apple Mail, Thunderbird, or another client, one of them may be deleting or syncing incorrectly. Temporarily remove the account from other devices or apps and test whether new mail still goes to Deleted Items.
If only specific emails are affected, Outlook may be treating conversation threads unusually. Check whether “Ignore Conversation” is enabled for those email threads. In Outlook, right-click the conversation and turn off Ignore. Ignored conversations automatically send future messages to Deleted Items.
You should also verify that no automatic cleanup settings are enabled. In Outlook desktop, Home > Clean Up can remove or move messages automatically within conversations.
If the issue started suddenly, it can also indicate account compromise. Check recent sign-in activity for your Microsoft account and change your password if you see unfamiliar access. Then remove unknown rules or forwarding settings.
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hth
Marcin