KB - No longer prompted to ZIP attachments

Issue

When sending an email you are no longer prompted to ZIP attachments.

Check Smartcrypt Settings

If you are not being prompted for all attachments, do you have ZIP Attachments enabled under Smartcrypt Options | Mail | General?

If you are only prompted for certain attachments, check the mail filter under Smartcrypt Options | Mail | General |Attachment Filter. Check to see if your file type is being excluded from the prompt.

Check Outlook Settings

Outlook may have disabled the ZIP Attachments add-in. Verify it is not on the disabled items list using the methods below:

Outlook 2007Outlook 2010
  • Launch Outlook
  • Click on Tools
  • Click Trust Center

  • Click Add-ins
  • Select Disabled items from the manage dropdown
  • Click Go

  • Enable PKZIP Attachments if it is on this list
  • Send a test email to yourself with an attachment
  • Launch Outlook
  • Click File
  • Click Options


  • Click Add-ins
  • Select Disabled items from the manage dropdown
  • Click Go


  • Enable PKZIP Attachments if it is on this list
  • Send a test email to yourself with an attachment