https://bugzilla.wikimedia.org/show_bug.cgi?id=56414

       Web browser: ---
            Bug ID: 56414
           Summary: Get mail relay out of Yahoo! blacklist
           Product: Wikimedia
           Version: unspecified
          Hardware: All
                OS: All
            Status: NEW
          Severity: normal
          Priority: Unprioritized
         Component: General/Unknown
          Assignee: [email protected]
          Reporter: [email protected]
                CC: [email protected], [email protected],
                    [email protected]
        Depends on: 56413
            Blocks: 52915
    Classification: Unclassified
   Mobile Platform: ---

X-YahooFilteredBulk: 208.80.152.133

(from
https://en.wikipedia.org/?oldid=579580929#WMF_notification_email_marked_as_spam_by_Yahoo
)

According to several comments, this means that our mail is currently
blacklisted by Yahoo!, so it's sent in the "Bulk" folder for users who have it
enabled (if not to spam?). WMF needs to send a "Bulk sender application for
whitelisting" http://help.yahoo.com/kb/index?page=content&id=SLN9042 but first
their guidelines have to be respected:
http://help.yahoo.com/kb/index?y=PROD_MAIL_ML&page=content&id=SLN3435

There are several things in there that we don't do; let's add each of them to
blockers when we're sure there's something to do.
* "Use email authentication such as DKIM": low-hanging fruit, let's do it as
soon as possible (bug 56413).
* "Be CAN-SPAM compliant": it's USA law, I assume we're respecting it. :) It
seems very lenient, from a quick skimming we're ok.
http://business.ftc.gov/documents/bus61-can-spam-act-compliance-guide-business
* "Consistently manage your lists": no idea, but MediaWiki surely doesn't
remove/disable addresses which bounce: I remember Brion mentioning this in some
2005 bug comment or something like that, I don't know if there's an open bug
but I'd say it's something worth doing. 
* "Segregate your mail streams by IP address and/or domain": in theory we do, I
can't judge if well enough.
* "Using your domain consistently": no idea, is it consistent to send from
[email protected] but then use @wikipedia.org, @mediawiki.org and so on to
From headers etc.?
* "Publish reverse DNS (PTR) records for your sending IPs": looks ok.
$ dig -x 208.80.152.133
;; ANSWER SECTION:
133.152.80.208.in-addr.arpa. 3552 IN    PTR     wiki-mail.wikimedia.org.
* "Secure your mail servers": I hope so.
* "Use common-sense settings": it would be nice to track this (Ori, do you know
something?), but Echo sends only few thousands notifications per day on en.wiki
(https://toolserver.org/~dartar/en/echo/ ) and standard enotif (talk and
watchlist) on all wikis is probably only one or two order of magnitudes bigger,
it's still a ridiculously low amount of emails, we're not DoS'ing Yahoo!. It's
possible that we have peaks, for instance an edit to a heavily watchlisted
pages could cause a peak of thousands enotifs in a single second, but I doubt
it's relevant. When we enabled enotifwatchlist on all wikis, the increased
network activity of mchenry wasn't even visible at all in ganglia.

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