iCloud mail-problems: TLS-problems?

[berndleutenecker]

Hi!

1) When sending e-mails to friends with icloud-accounts
from my exchange-account (via Outlook using IMAP/SMTP)
neither these friends receive my e-mails nor do I receive an
error-message of any kind.
As usual I do find copies of these e-mails in my sent-folder.

I am using TLS for IMAP (port 143) and SMTP (port 25).

Sending to any other e-mail-address does not show such
problems.

My friends can't find any trace of my e-mails, they are
not marked as spam, moved to another folder etc.

Whenever a message has a problem, the sender should
be notified about that - but I never have received such a
notification in that case.

2) When sending from Outlook Web Access to these iCloud-
addresses my e-mails do arrive in the inbox of the
recipients.

3) When I answer within Outlook an e-mail received from
one of my friends with iCloud-accounts there is no problem.

In any case the header-informations are not the same,
that's all I can find.
Is there a problem using TLS? But I guess that answering
to an e-mail should not show any difference than writing
a new message; each time my SMTP-settings should
be used.

As many people have iCloud-e-mail-addresses I would
like to find the reason behind this problem - and even
more a solution ...

Thank you!

Bernd

 

[twerppoet]

It might be silent filtering.

Apple has been known to use a silent filter for certain phrases in the past. Emails filtered by this method do not end up in the junk folder, not does the sender get a notification. In general, these are phrases you would never see in a legitimate, non-spam, email; but since no filtering list is perfect it's possible you've been caught on this.

You said the header was different. That seems unlikely to cause issues, though I suppose some meta-data in the header could cause filtering. I'd try send identical emails using both methods (including any automatic signatures) and see fi you can track down the problem phrase.

That is assuming that silent filtering is the issue. It might not be, and if it is not I have no idea what the problem is.

You can do a Google Search for iCloud silent filtering for more information. It was a hot topic, briefly, in 2013, and is mentioned a couple of times after that. The only reason I can think of that the media dropped it is because it doesn't crop up often enough to be an issue for a significant number of people.

Of course that doesn't help if you turn out to be one of those few that it affects.