Hi postfix users,
I’m new here. I have setup postfix recently on my AWS instance and things work 
pretty well. I can read (dovecot) and sent (postfix) and all works well. I 
experienced some uncertainty lately and i was hoping maybe one of you could 
assist me, or maybe you experienced this before, yourself.

1. DKIM. This is not really postfix related but if anyone knows i’d appreciate 
it. When i send mail from my domain to another domain (say outlook) it adds the 
signature field and is fine.
Aug 16 08:58:56 www postfix/cleanup[12690]: 4A61A63F61: 
message-id=<e09e3d20-fbfb-44ea-9cdd-24082d934...@mydomain.com<mailto:e09e3d20-fbfb-44ea-9cdd-24082d934...@mydomain.com>>
Aug 16 08:58:56 www opendkim[13789]: 4A61A63F61: DKIM-Signature field added 
(s=default, d=mydomain.com<http://mydomain.com>)
Aug 16 08:58:56 www postfix/qmgr[14386]: 4A61A63F61: 
from=<sa...@mydomain.com<mailto:sa...@mydomain.com>>, size=778, nrcpt=1 (queue 
active)

When i get an email from outlook.com<http://outlook.com> i see this. Is that 
normal ? Worried slightly about the not authenticated and failed to parse 
messages.
Aug 16 09:01:47 www postfix/cleanup[12710]: B609463F61: 
message-id=<db5pr03mb11111d02543e8f7833add9e9c9...@db5pr03mb1111.eurprd03.prod.outlook.com<mailto:db5pr03mb11111d02543e8f7833add9e9c9...@db5pr03mb1111.eurprd03.prod.outlook.com>>
Aug 16 09:01:47 www opendkim[13789]: B609463F61: 
mail-oln040092068076.outbound.protection.outlook.com<http://mail-oln040092068076.outbound.protection.outlook.com>
 [40.92.68.76] not internal
Aug 16 09:01:47 www opendkim[13789]: B609463F61: not authenticated
Aug 16 09:01:47 www opendkim[13789]: B609463F61: failed to parse 
authentication-results: header field
Aug 16 09:01:47 www opendkim[13789]: B609463F61: DKIM verification successful
Aug 16 09:01:47 www postfix/qmgr[14386]: B609463F61: 
from=<u...@outlook.com<mailto:u...@outlook.com>>, size=5355, nrcpt=1 (queue 
active)

2. Why do i sometimes get a anonymous TLS connection.
Aug 16 09:01:47 www postfix/smtpd[12706]: SSL_accept:SSLv3 flush data
Aug 16 09:01:47 www postfix/smtpd[12706]: Anonymous TLS connection established 
from 
mail-oln040092068076.outbound.protection.outlook.com<http://mail-oln040092068076.outbound.protection.outlook.com>[40.92.68.76]:
 TLSv1.2 with cipher AES256-SHA256 (256/256 bits)

And sometimes a regular TLS connection ? Same ip and same cipher as well.
Aug 16 09:01:47 www postfix/smtpd[12706]: initializing the server-side TLS 
engine
Aug 16 09:01:47 www postfix/smtpd[12706]: connect from 
mail-oln040092068076.outbound.protection.outlook.com<http://mail-oln040092068076.outbound.protection.outlook.com>[40.92.68.76]
Aug 16 09:01:47 www postfix/smtpd[12706]: setting up TLS connection from 
mail-oln040092068076.outbound.protection.outlook.com<http://mail-oln040092068076.outbound.protection.outlook.com>[40.92.68.76]
Aug 16 09:01:47 www postfix/smtpd[12706]: 
mail-oln040092068076.outbound.protection.outlook.com<http://mail-oln040092068076.outbound.protection.outlook.com>[40.92.68.76]:
 TLS cipher list "ALL:+RC4:@STRENGTH"

Aug 16 09:01:47 www postfix/smtpd[12706]: Anonymous TLS connection established 
from 
mail-oln040092068076.outbound.protection.outlook.com<http://mail-oln040092068076.outbound.protection.outlook.com>[40.92.68.76]:
 TLSv1.2 with cipher AES256-SHA256 (256/256 bits)

3. Finally, i have this bizarre problem where 2 of my iMacs at home cannot 
connect to my mail server anymore. MacBook and iPhone work fine (although i had 
some problems with iPhone as well). It seems like a local issue (as i’m sure 
anyone would say) but i can’t for the life figure out what it is. All i get on 
the maillog is this:
Aug 16 09:01:47 www postfix/smtpd[12706]: read from 5565938E6820 [556593910343] 
(5 bytes => -1 (0xFFFFFFFFFFFFFFFF))

I tried deleting the accounts and re-adding, but it just says cannot verify 
mail server, and then just waits for a long time. Is this certificate/SSL 
related? It sure feels like it. Should i turn off SSL to test ?

4. Finally, does anyone know what to do to get through to 
outlook.com<http://outlook.com> addresses? Smartscreen filters all the email 
into junk. I added SPF, DKIM, DMARC, a PTR record, SenderID etc but when i 
contact the microsoft delivery team all i get is : "Not eligible for 
mitigation”.
My address is, while in the Amazon AWS pool, an elastic ip address and it is 
not on any spam or RBL’s. I owned it for 6 months or so, including the domain.

Gmail or yahoo has no problem receiving it in the normal mailbox. And as 
microsoft is not giving me any real pointers as to why it is being filtered, 
i’m not sure what else to do.
I can send the postconf -n upon request.
Alef

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