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Re:Email Explained from First Principles by alexpotato on Saturday May 08, 2021 @12:55PM (#27088811)
Back in the early 2000's I worked for a company that was the lead firm doing analysis of email spammers for later targeting by the law firms of the big free email providers.

The phrase "be liberal in what you accept, and conservative in what you send" certainly applied to SMTP which led to all kinds of craziness in spam.

For example:

- Emails with multiple "From" fields in the headers

- Totally bogus relay chain data

- all kinds of other garbage in random fields

- sender IPs that were faked etc

This was also around the time that spammers were switching to using bas64 MIME encoded images to get around text filters.

The company I worked for actually got pretty good at analysing the spam thanks to a combination of a IMDB style web based browser for the spam I put together and good old fashioned "leg work" to track the owner of URLs, merchant accounts etc. That in turn led to some of the spammers actually shutting down.

More details here: https://twitter.com/alexpotato/status/1208948480867127296

Re:Email Explained from First Principles by walrus01 on Saturday May 08, 2021 @04:58PM (#27090616)
> - Totally bogus relay chain data

- all kinds of other garbage in random fields

- sender IPs that were faked etc

Anyone interested in looking at all the possible permutations of spam, can view the spamassassin rule sets which are quite comprehensive by now. Spamassassin has been around for close to 20 years.

Re:Email Explained from First Principles by romanixromanix on Saturday May 08, 2021 @03:00PM (#27089809)
>> Emails with multiple "From" fields in the headers

Do you think this is still possible?

Re:Email Explained from First Principles by gumby on Saturday May 08, 2021 @04:03PM (#27090217)
Sure better be, for the sake of backwards compatibility.

This isn't a problem for mail transport as the recipient is specified in the envelope and the message itself is not examined.

What a client should do in such a case is unclear. I suspect that they all use the first one encountered and ignore the rest.

Re:Email Explained from First Principles by secabeen on Saturday May 08, 2021 @04:44PM (#27090516)
Multiple From: fields are allowed by https://tools.ietf.org/html/rfc5322#section-3.6.2 as long as a Sender: is also included.
Re:Email Explained from First Principles by KasparEtter on Sunday May 09, 2021 @03:45AM (#27094072)
Just to be precise: It's a single From field with several addresses, not multiple From fields (see https://tools.ietf.org/html/rfc5322#page-21).

RFC 6854 updated the From field to allow an empty group construct (see https://explained-from-first-principles.com/email/#no-reply) but mainly for other reasons (see https://explained-from-first-principles.com/email/#email-add...).

DMARC authentication either rejects multiple addresses in the From field or authenticates them all and applies the most strict policy (see https://explained-from-first-principles.com/email/#domain-ba...).