When you install Outlook, an Inbox repair tool (scanpst.exe) is also installed on your PC. The Inbox repair tool can resolve problems by scanning your Outlook data files, and repairing errors. To use the Inbox repair tool, exit Outlook, and then follow the steps in Repair Outlook Data Files (.pst and.ost). The certificate name mismatch causes Outlook to present the warning that is mentioned in the 'Symptoms' section. When you view the details of the certificate by clicking Show Certificate, you see a warning message in the certificate details that states the following: This certificate is not valid (host name mismatch). How to Restore the Forgotten Attachment Warning in Outlook on the Web July 7, 2016 by Paul Cunningham 3 Comments Outlook on the Web (what used to be called OWA) has a useful feature that checks an email you’re about to send, and if it contains words that indicate that there should be a file attached to the message, will warn you that nothing.

Outlook on the Web (what used to be called OWA) has a useful feature that checks an email you’re about to send, and if it contains words that indicate that there should be a file attached to the message, will warn you that nothing has been attached. It’s very nice, and it’s something we’ve all done once or twice or a few hundred times over the years, so I certainly appreciate the warning.

Included in the warning is that tick box to tell Exchange “Don’t show me this message again.” Obviously that tick box exists to cater to what is surely a small number of people who frequently mention words like “attachment” or “attached” without actually attaching anything to the email message, and therefore don’t want to be nagged about it all the time. But of course, it also means that normal people are going to tick that box by accident, and then complain when “that warning that usually appears didn’t show up and I accidentally sent an email without an attachment!”

Fortunately, the setting is controlled in the message configuration for the mailbox as an attribute named CheckForForgottenAttachments, which can be checked by running Get-MailboxMessageConfiguration.

Outlook Attachment Warning Disable

It shows trying to sync inbox 0/2, it will eventually got to 1/2 and then sync complete but has 2 errors that the attachment could not be synced because it was too large. We found the email w/ the attachment - deleted the attachment and the email but it still tries to sync the 2 instances. I too have a user who continues to get the 'Attachment Security Warning' AFTER uninstalling KB3191898 (Outlook 2007). I also tried several of the MS fixes in the registry - 'AllowUnregisteredMapiServices' as well as 'Level1Remove' The specific file type causing issues is Adobe PDF's.

Mac
Outlook For Mac Attachments Warning
[PS]C:>Set-MailboxMessageConfiguration-Identity adam.wally@exchangeserverpro.net-CheckForForgottenAttachments$true

The user may need to log out and in to Outlook on the Web, or at least do a refresh in their browser, for the setting to take effect again.