Microsoft Outlook can use three types of message format:
Using RTF with PGP encryption can result in missing annotations:
This occurs whether PGP Encryption Desktop or PGP Encryption Gateway is used to encrypt or decrypt messages.
PGP Encryption Server and PGP Encryption Desktop 10.5 and above.
If the body of the outbound RTF message only contains formatted text, whether or not the message has an attachment, recent releases of Outlook will automatically convert the RTF message body to HTML format. The raw message will include a text/html section with this comment:
<!-- Converted from text/rtf format -->
However, if the message contains inline graphics, no conversion to HTML takes place and instead all rich text formatting and inline graphics are contained in a binary winmail.dat attachment. This winmail.dat file is encrypted by the sender's PGP Encryption Desktop or Server and decrypted by the recipient's PGP Encryption Desktop or Server. Outlook then decodes the winmail.dat file. Because winmail.dat is a binary file, no annotations can be added by PGP Encryption Desktop or Server.
There are two main ways of working around this issue: