This week a customer had the following problem, some items in several mailboxes couldn’t be deleted in Outlook and Outlook Web App. When trying to delete the message in OWA, the following error was presented: “Some items cannot be deleted. They were either moved, already deleted, or access was denied”

After a bit of investigation I noticed that the “undeletable”messages where bigger than the send and receive limits set on the Server (receive connectors) and Transport (transport config and send connector) level. So I went on the Internet and came across the Blog of Network Steve where he explained the same issue.

In this case the customer was migrated from Groupwise to Exchange 2010 SP1 a while ago, during the migration (with Quest) several mailboxes were failed because of the message size limits that were preset in the Exchange environment. The messages that were to big were rejected, so because of the migration the limits were temporary set to a higher number. Setting these limits to a higher level of course gave the users a change to send and receive bigger email messages. 

Normally you will receive error’s like in the pictures below, but since the message size limits were set to a higher value the migrated messages were already in the Exchange Mailbox Database before setting the receive and send limits to a lower figure. 

For me the fix was setting the receive and send limits to a higher number. (25MB) After a while of synchronizing, the messages could be deleted. Another fix was to delete the attachments in Outlook first before deleting the message. This issue looks like a bug, it doesn’t make sense why you cannot normally delete a message that is to big.

Deleting a message in Exchange will normally result in that the message can be undeleted for 14 days (default value) when you have the “Keep deleted items for (days)” set on 14 days. Disabling this option will not fix the described issue. It was just a though since the message is actually moved instead of being deleted.