Deleted emails do not appear in trash

Give this a try: boot into Safe Mode according to How to use safe mode on your Mac and test to see if the problem persists. Reboot normally and test again.

NOTE 1: Safe Mode boot can take up to 3 - 5 minutes as it's doing the following; 

• Verifies your startup disk and attempts to repair directory issues, if needed

• Loads only required kernel extensions (prevents 3rd party kernel/extensions from loading)

• Prevents Startup Items and Login Items from opening automatically

• Disables user-installed fonts 

• Deletes font caches, kernel cache, and other system cache files

NOTE 2: if you have a wireless keyboard with rechargeable batteries connect it with its charging cable before booting into Safe Mode. This makes it act as a wired keyboard as will insure a successful boot into Safe Mode.

My settings are all set correctly to never delete, however currently today I can't get to emails before 6/21/2023. I don't understand why I can't get to an email that I need on 6/11 no matter how I try.

I am not understanding how this would help? If it is all cloud based, wouldn't it show up in the cloud on Apple Web portal as well? This is all iCloud emails, but doesn't matter where I go, I am not seeing emails past 6/21.

If you have deleted your emails on your Mac mini and they are not appearing in the Trash folder, it could be due to several reasons. Here are some troubleshooting steps you can try:

1. Check different folders: Sometimes, emails may get inadvertently moved to other folders instead of the Trash. Check your other email folders such as Archive, Junk, or any custom folders you may have created.

2. Search for the deleted emails: Use the search function in your email client to look for the deleted emails. Enter relevant keywords or the sender's email address to narrow down the search results and locate the missing emails.

3. Empty the Trash folder: It's possible that the deleted emails are still in the Trash folder but not visible due to a display issue. Try emptying the Trash folder to force a refresh. Right-click on the Trash folder and select "Empty Trash" or a similar option to remove all items.

4. Verify mailbox synchronization: If you're using an email client like Apple Mail, make sure that your email account is properly configured for synchronization. Go to the Mail preferences and check the settings for your email account, including the synchronization options. Ensure that the "Move deleted messages to the Trash mailbox" option is enabled.

5. Check server settings: If you're using an IMAP or Exchange email account, verify the server settings and ensure that they are correctly configured. Incorrect settings may result in deleted emails not being properly moved to the Trash folder on the server. Refer to your email service provider's documentation or contact their support for assistance in checking the server settings.

6. Contact your email service provider: If the above steps don't resolve the issue, it's recommended to reach out to your email service provider's support team. They can investigate the problem on their end and provide specific guidance based on your account configuration.

Remember to always keep backups of important emails to avoid data loss in situations like these. Regularly backing up your emails ensures you have a copy of them even if they are accidentally deleted or go missing from the Trash folder.

Can you go through this article and make sure you are set up to insure emails are not erased?

Delete emails in Mail on Mac - Apple Support

Often a cache or swap file can get corrupted and cause a number of seemingly unrelated problems throughout a Mac. It also verifies the startup disk and repairs any anomalies it finds.