On Fri, 26 Aug 2022, post...@ptld.com wrote:

 EMAIL HEADER
 Subject: =?UTF-8?B?8J+YsSBTSE9QIE5PVzogR2V0IDAlIElOVEVSRVNUIERlYWxzIHBs?=
  =?UTF-8?B?dXMgZXhjbHVzaXZlIHZvdWNoZXJzIHdpdGggU1BheUxhdGVyISDwn5GJ?=

 SIDE BY SIDE COMPARE
 =?UTF-8?B?8J+YsSBTSE9QIE5PVzogR2V0IDAlIElOVEVSRVNUIERlYWxzIHBs?=
 =?UTF-8?B?dXMgZXhjbHVzaXZlIHZvdWNoZXJzIHdpdGggU1BheUxhdGVyISDwn5GJ?=
 =?UTF-8?B?8J+YsSBTSE9QIE5PVzogR2V0IDAlIElOVEVSRVNUIERlYWxzIHBs?=?
 =?UTF-8?B?dXMgZXhjbHVzaXZlIHZvdWNoZXJzIHdpdGggU1BheUxhdGVyISDwn5GJ?=

 You missed the newline in the first line.  Postfix will obviously not
 let those through and will replace such characters with '?' or so.  It
 does not interpret stuff.

Can you elaborate more? What do you mean I missed the new line? The email header subject being two lines? What did i miss about it? Isn't that how it is supposed to be? And why would postfix insert a '?' just because line breaks were used when it's expected on long lines? Wietse just said "Postfix (and Postfix logging) does not alter subject lines".

The subject line is just one line, but in the example you posted it had been split into two lines, so the actual subject had a space in the middle, which must be quoted (i.e. " " becomes "? ").

Check RFC5322, section 2.2.1 "Unstructured Header Field Bodies".
  Semantically, unstructured field bodies are simply to be treated as a
  single line of characters with no further processing (except for
  "folding" and "unfolding" as described in section 2.2.3).

where 2.2.3 ("Long Header Fields") explains the "folding", e.g.

Subject: This is a test

can be represented as:

Subject: This
 is a test

After "This" you have a (quoted) space, not a CR/LF.

Hope that helps,
Bernardo

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