Back in my first post, Ludovic kindly posted, in a comment, a link to a talk of someone else's email rant. And the best place to start this post is with a quote from that talk: "If you want to see an email programmer's face turn red, ask him about CFWS." CFWS is an acronym that stands for "comments and folded whitespace," and I can attest that the mere mention of CFWS is enough for me to start ranting. Comments in email headers are spans of text wrapped in parentheses, and the folding of whitespace refers to the ability to continue headers on multiple lines by inserting a newline before (but not in lieu of) a space.
I'll start by pointing out that there is little advantage to adding in free-form data to headers which are not going to be manually read in the vast majority of cases. In practice, I have seen comments used for only three headers on a reliable basis. One of these is the Date header, where a human-readable name of the timezone is sometimes included. The other two are the Received and Authentication-Results headers, where some debugging aids are thrown in. There would be no great loss in omitting any of this information; if information is really important, appending an X- header with that information is still a viable option (that's where most spam filtration notes get added, for example).
For this feature of questionable utility in the first place, the impact it has on parsing message headers is enormous. RFC 822 is specified in a manner that is familiar to anyone who reads language specifications: there is a low-level lexical scanning phase which feeds tokens into a secondary parsing phase. Like programming languages, comments and white space are semantically meaningless . Unlike programming languages, however, comments can be nested—and therefore lexing an email header is not regular . The problems of folding (a necessary evil thanks to the line length limit I keep complaining about) pale in comparison to comments, but it's extra complexity that makes machine-readability more difficult.
Fortunately, RFC 2822 made a drastic change to the specification that greatly limited where CFWS could be inserted into headers. For example, in the Date header, comments are allowed only following the timezone offset (and whitespace in a few specific places); in addressing headers, CFWS is not allowed within the email address itself . One unanticipated downside is that it makes reading the other RFCs that specify mail headers more difficult: any version that predates RFC 2822 uses the syntax assumptions of RFC 822 (in particular, CFWS may occur between any listed tokens), whereas RFC 2822 and its descendants all explicitly enumerate where CFWS may occur.
Beyond the issues with CFWS, though, syntax is still problematic. The separation of distinct lexing and parsing phases means that you almost see what may be a hint of uniformity which turns out to be an ephemeral illusion. For example, the header parameters define in RFC 2045 for Content-Type and Content-Disposition set a tradition of ;-separated param=value attributes, which has been picked up by, say, the DKIM-Signature or Authentication-Results headers. Except a close look indicates that Authenticatin-Results allows two param=value pairs between semicolons. Another side effect was pointed out in my second post: you can't turn a generic 8-bit header into a 7-bit compatible header, since you can't tell without knowing the syntax of the header which parts can be specified as 2047 encoded-words and which ones can't.
There's more to headers than their syntax, though. Email headers are structured as a somewhat-unordered list of headers; this genericity gives rise to a very large number of headers, and that's just the list of official headers. There are unofficial headers whose use is generally agreed upon, such as X-Face, X-No-Archive, or X-Priority; other unofficial headers are used for internal tracking such as Mailman's X-BeenThere or Mozilla's X-Mozilla-Status headers. Choosing how to semantically interpret these headers (or even which headers to interpret!) can therefore be extremely daunting.
Some of the headers are specified in ways that would seem surprising to most users. For example, the venerable From header can represent anywhere between 0 mailboxes  to an arbitrarily large number—but most clients assume that only one exists. It's also worth noting that the Sender header is (if present) a better indication of message origin as far as tracing is concerned , but its relative rarity likely results in filtering applications not taking it into account. The suite of Resent-* headers also experiences similar issues.
Another impact of email headers is the degree to which they can be trusted. RFC 5322 gives some nice-sounding platitudes to how headers are supposed to be defined, but many of those interpretations turn out to be difficult to verify in practice. For example, Message-IDs are supposed to be globally unique, but they turn out to be extremely lousy UUIDs for emails on a local system, even if you allow for minor differences like adding trace headers .
More serious are the spam, phishing, etc. messages that lie as much as possible so as to be seen by end-users. Assuming that a message is hostile, the only header that can be actually guaranteed to be correct is the first Received header, which is added by the final user's mailserver . Every other header, including the Date and From headers most notably, can be a complete and total lie. There's no real way to authenticate the headers or hide them from snoopers—this has critical consequences for both spam detection and email security.
There's more I could say on this topic (especially CFWS), but I don't think it's worth dwelling on. This is more of a preparatory post for the next entry in the series than a full compilation of complaints. Speaking of my next post, I don't think I'll be able to keep up my entirely-unintentional rate of posting one entry this series a month. I've exhausted the topics in email that I am intimately familiar with and thus have to move on to the ones I'm only familiar with.
 Some people attempt to be to zealous in following RFCs and ignore the distinction between syntax and semantics, as I complained about in part 4 when discussing the syntax of email addresses.
 I mean this in the theoretical sense of the definition. The proof that balanced parentheses is not a regular language is a standard exercise in use of the pumping lemma.
 Unless domain literals are involved. But domain literals are their own special category.
 Strictly speaking, the 0 value is intended to be used only when the email has been downgraded and the email address cannot be downgraded. Whether or not these will actually occur in practice is an unresolved question.
 Semantically speaking, Sender is the person who typed the message up and actually sent it out. From is the person who dictated the message. If the two headers would be the same, then Sender is omitted.
 Take a message that's cross-posted to two mailing lists. Each mailing list will generate copies of the message which end up being submitted back into the mail system and will typically avoid touching the Message-ID.
 Well, this assumes you trust your email provider. However, your email provider can do far worse to your messages than lie about the Received header…