Hi @Melanie Ouellette ,
What's the type of your account(POP, IMAP, Exchange)?
As you mentioned, this issue seems to be a problem that has only recently occurred, so what special operations did you perform before this issue happened?
outlook has decided to no longer send my deleted emails to the folder
Could you normally delete emails in other folders (such as Sent Items or Drafts)?
How did you delete your mails? As I know, there are multiple ways to delete emails in Outlook client such as right-click the emails > choose delete, click “Delete” key on keyboard or directly drag emails into Deleted Items folder. It’s suggested to switch other ways to delete for tests and check if the issue has any difference.
Besides, to confirm if you have already permanently delete those emails, it is also suggested to try to search them within your Deleted Items folder and see if you could find any results.
I tested with my exchange account to delete Inbox emails on the Outlook 365(Version 2007 Build 13029 .20344 Click-to-Run), and it can work fine like you said ”delete a message from your inbox and it goes into your deleted folder”. As I know, the interference of add-ins may cause this issue, in order to conduct further researches on your issue, please try to open your Outlook in safe mode(Windows + R > type “outlook.exe /safe”).
Any update, please feel free to post back.
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