This is good advice but let's not ignore the simplest answer as well. If
you have a Hotmail/Outlook/Office365 account there's a good chance that
you have emails from Microsoft in your spam folder. The first time I
signed up for Office 365 to test their inbox/spam folder behavior, their
email welcoming me to Office 365 was right there in the spam folder. If
Microsoft can't deliver their own emails to their own inboxes, good luck
to the rest of us.
On 2022-06-01 16:39, Sebastian Nielsen via mailop wrote:
I suspect your webmail system is putting certain headers in the email,
that Hotmail/Outlook detects, and Hotmail/Outlook have detected a
issue with the particular webmail system, like a security issue that
allows unauthorized users to send spam through the webmail system,
causing Hotmail/Outlook to blanket block that particular webmail
software.
My suggestion: Send an email to yourself from the webmail system, and
then from a desktop client.
Compare the headers. Then set up your outgoing SMTP server, to
dump/modify those headers that the webmail system is putting in,
effectively hiding that the mails are sent by that particular webmail
software.
NOTE: ONLY do this after you are sure that there is no issues with
your installation of webmail software (ero either upgraded to latest
version, or any security holes back-ported and patched). Else you risk
either getting blocked, or causing other issues like Thunderbird
becoming spam filtered (however pretty low risk of that).
Från: Rob McEwen via mailop <mailop@mailop.org>
Skickat: den 1 juni 2022 23:26
Till: mailop <mailop@mailop.org>
Ämne: [mailop] outlook/hotmail (silently!) putting legit msgs into
"Junk Email" folder
RE: outlook/hotmail (silently!) putting legit msgs into "Junk Email"
folder
All of a sudden - my users are having either all or most of their
webmail-sent legit hand-typed messages going to outlook/hotmail -
placed into outlook/hotmail's "Junk Email" folder - specifically, when
logged into the outlook/hotmail webmail site. But if the same message
is instead sent by the user from their Outlook Desktop app or
Thunderbird, it works. Fwiw, the accounts I tested had SFP and DMARK
setup and working correctly. (fwiw, I'm using the same webmail setup
that I've used for a long time - no recent changes there.)
I've reached out to some of my contacts at Microsoft - so I'm waiting
to hear back from them - but in the meantime - is anyone else seeing
this? Any suggestions?
The kind of messages getting blocked - would be the kind that I would
be embarrassed by if my system were blocking such hand-typed not-spam
business emails - this must be overzealous spam filtering - but if, in
the meantime, I could find a workaround to get past this, that would
be great!
Also, I think this is appropriate for Mail Op because (1) others could
be having this issue too, but not even be aware of this yet? These
message are getting "250 OK" responses, so this won't get noticed as
quickly! and (2) messages going to outlook/hotmail are a statistically
significant percentage of all email, so this might be a new issue
impacting many many people.
--
Rob McEwen, invaluement
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