An electronic mail encryption mechanism must be compatible with the transparency constraints of its underlying electronic mail facilities. These constraints are generally established based on expected user requirements and on the characteristics of anticipated endpoint and transport facilities. An encryption mechanism must also be compatible with the local conventions of the computer systems which it interconnects. Our approach uses a canonicalization step to abstract out local conventions and a subsequent encoding step to conform to the characteristics of the underlying mail transport medium (SMTP). The encoding conforms to SMTP constraints. Section 4.5 of RFC 821  details SMTP's transparency constraints.
To prepare a message for SMTP transmission, the following requirements must be met:
Although SMTP specifies a standard representation for line delimiters (ASCII <CR><LF>), numerous systems in the Internet use a different native representation to delimit lines. For example, the <CR><LF> sequences delimiting lines in mail inbound to UNIX systems are transformed to single <LF>s as mail is written into local mailbox files. Lines in mail incoming to record-oriented systems (such as VAX VMS) may be converted to appropriate records by the destination SMTP server . As a result, if the encryption process generated <CR>s or <LF>s, those characters might not be accessible to a recipient UA program at a destination which uses different line delimiting conventions. It is also possible that conversion between tabs and spaces may be performed in the course of mapping between inter-SMTP and local format; this is a matter of local option. If such transformations changed the form of transmitted ciphertext, decryption would fail to regenerate the transmitted plaintext, and a transmitted MIC would fail to compare with that computed at the destination.
The conversion performed by an SMTP server at a system with EBCDIC as a native character set has even more severe impact, since the conversion from EBCDIC into ASCII is an information-losing transformation. In principle, the transformation function mapping between inter-SMTP canonical ASCII message representation and local format could be moved from the SMTP server up to the UA, given a means to direct that the SMTP server should no longer perform that transformation. This approach has a major disadvantage: internal file (e.g., mailbox) formats would be incompatible with the native forms used on the systems where they reside. Further, it would require modification to SMTP servers, as mail would be passed to SMTP in a different representation than it is passed at present.