Mail doesn't reach the addressee

my problem a mail doesn’t reach the addressee on icloud.com though in mail.log there are no errors or warnings

root@box:~# echo ‘test eMial’ | mail -s ‘test subject’ appleid@me.com
root@box:~# tail -n 35 -f /var/log/mail.log
tail result -> https://gist.github.com/anonymous/93c545788e3af17aba79

Strange indeed, I just tried to send an email to an .icloud address and it work like a charm. Tailing /var/log/mail.log gave me the same result as yours.

You can do a checkup on your email address using the allaboutspam.com service.
It should give you hints about what may be wrong with your box.

@SaliVan, did you check your spam folder on icloud?

Check that the system status page at /admin doesn’t show any problems. Try @buraitopengin link. If neither of those reveals a problem, post again and we’ll keep looking.

spam folder on icloud is empty!

system check report

[![](https://www.dropbox.com/s/cfemjuvr7ik99j8/Скриншот 2014-12-01 14.34.54.png?dl=1)]

i try @buraitopengin link. All results are green other than these two
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Oh, just a moment, I just re-read your initial post.

Does this happen just when you send mail from the command line, or also when you send mail from a normal mail client?

yes the same thing if I send a ‘Mail-in-a-Box / Roundcube Webmail’

Can you send me an email (jt@occams.info)? I can try to see if anything is wrong from the mail headers.

It could also be that iCloud just doesn’t like you / your ip / your domain. Things like that happen.

you receive an email?

Dec  1 16:03:09 box postfix/smtp[14012]: setting up TLS connection to box.occams.info[94.76.*.*]:25
Dec  1 16:03:09 box postfix/smtp[14012]: box.occams.info[94.76.*.*]:25: TLS cipher list "aNULL:-aNULL:ALL:!EXPORT:!LOW:+RC4:@STRENGTH:!aNULL"
Dec  1 16:03:09 box postfix/smtp[14012]: looking for session smtp&occams.info&box.occams.info&94.76.*.*&&EDD03C79CCE9EE55C528987DA27B22559097DA5009C7D53A4F8B8A50F525B06C in smtp cache
Dec  1 16:03:09 box postfix/tlsmgr[13488]: lookup smtp session id=smtp&occams.info&box.occams.info&94.76.*.*&&EDD03C79CCE9EE55C528987DA27B22559097DA5009C7D53A4F8B8A50F525B06C
Dec  1 16:03:09 box postfix/smtp[14012]: box.occams.info[94.76.*.*]:25: SNI hostname: box.occams.info
Dec  1 16:03:09 box postfix/smtp[14012]: SSL_connect:before/connect initialization
Dec  1 16:03:09 box postfix/smtp[14012]: SSL_connect:unknown state
Dec  1 16:03:09 box postfix/smtp[14012]: SSL_connect:SSLv3 read server hello A
Dec  1 16:03:09 box postfix/smtp[14012]: box.occams.info[94.76.*.*]:25: depth=3 verify=1 subject=/C=US/O=Equifax/OU=Equifax Secure Certificate Authority
Dec  1 16:03:09 box postfix/smtp[14012]: box.occams.info[94.76.*.*]:25: depth=2 verify=1 subject=/C=US/O=GeoTrust Inc./CN=GeoTrust Global CA
Dec  1 16:03:09 box postfix/smtp[14012]: box.occams.info[94.76.*.*]:25: depth=1 verify=1 subject=/C=US/O=GeoTrust, Inc./CN=RapidSSL CA
Dec  1 16:03:09 box postfix/smtp[14012]: box.occams.info[94.76.*.*]:25: depth=0 verify=1 subject=/serialNumber=OyPBD/rAziqKWnBgFmancxa3zVL2nssw/OU=GT24358451/OU=See www.rapidssl.com/resources/cps (c)14/OU=Domain Control Validated - RapidSSL(R)/CN=box.occams.info
Dec  1 16:03:09 box postfix/smtp[14012]: SSL_connect:SSLv3 read server certificate A
Dec  1 16:03:09 box postfix/smtp[14012]: SSL_connect:SSLv3 read server key exchange A
Dec  1 16:03:09 box postfix/smtp[14012]: SSL_connect:SSLv3 read server done A
Dec  1 16:03:09 box postfix/smtp[14012]: SSL_connect:SSLv3 write client key exchange A
Dec  1 16:03:09 box postfix/smtp[14012]: SSL_connect:SSLv3 write change cipher spec A
Dec  1 16:03:09 box postfix/smtp[14012]: SSL_connect:SSLv3 write finished A
Dec  1 16:03:09 box postfix/smtp[14012]: SSL_connect:SSLv3 flush data
Dec  1 16:03:09 box postfix/smtp[14012]: SSL_connect:SSLv3 read finished A
Dec  1 16:03:09 box postfix/smtp[14012]: save session smtp&occams.info&box.occams.info&94.76.*.*&&EDD03C79CCE9EE55C528987DA27B22559097DA5009C7D53A4F8B8A50F525B06C to smtp cache
Dec  1 16:03:09 box postfix/tlsmgr[13488]: put smtp session id=smtp&occams.info&box.occams.info&94.76.*.*&&EDD03C79CCE9EE55C528987DA27B22559097DA5009C7D53A4F8B8A50F525B06C [data 1441 bytes]
Dec  1 16:03:09 box postfix/tlsmgr[13488]: write smtp TLS cache entry smtp&occams.info&box.occams.info&94.76.*.*&&EDD03C79CCE9EE55C528987DA27B22559097DA5009C7D53A4F8B8A50F525B06C: time=1417449789 [data 1441 bytes]
Dec  1 16:03:09 box postfix/smtp[14012]: box.occams.info[94.76.*.*]:25: depth=0 matched end entity certificate sha256 digest 7B:22:1D:C3:DD:37:B8:71:F6:44:91:1B:F7:EE:7A:33:FD:66:BB:4A:30:7C:69:EE:7D:2B:38:55:67:24:44:9E
Dec  1 16:03:09 box postfix/smtp[14012]: box.occams.info[94.76.*.*]:25: subject_CN=box.occams.info, issuer_CN=RapidSSL CA, fingerprint=5D:6A:A5:EA:A6:67:DE:64:53:6C:48:70:B0:9F:0D:0F, pkey_fingerprint=69:6E:98:78:8B:6F:99:D2:FE:B4:D9:61:CE:67:D1:8C
Dec  1 16:03:09 box postfix/smtp[14012]: Verified TLS connection established to box.occams.info[94.76.*.*]:25: TLSv1.2 with cipher ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits)
Dec  1 16:03:10 box postfix/smtp[14012]: 90C7842F6E: to=<jt@occams.info>, relay=box.occams.info[94.76.*.*]:25, delay=5.5, delays=0.29/0.03/3.4/1.7, dsn=4.2.0, status=deferred (host box.occams.info[94.76.*.*] said: 450 4.2.0 <jt@occams.info>: Recipient address rejected: Greylisted, see http://postgrey.schweikert.ch/help/occams.info.html (in reply to RCPT TO command))

........................................................................................................................

Dec  1 16:14:03 box postfix/smtp[14053]: initializing the client-side TLS engine
Dec  1 16:14:33 box postfix/smtp[14053]: connect to box.occams.info[94.76.202.152]:25: Connection timed out
Dec  1 16:14:33 box postfix/smtp[14053]: 90C7842F6E: to=<jt@occams.info>, relay=none, delay=688, delays=658/0.02/30/0, dsn=4.4.1, status=deferred (connect to box.occams.info[94.76.202.152]:25: Connection timed out)

I got it, yes. I’ll take a look later today or tomorrow.

have any news for me?

Actually I don’t see any problem. I’m not sure what’s going on, sorry!

I’ll send a message to “jt@occams.info” from my email "b...v@me.com" could answer it with your MailBox, I want to check if the letter reach from other MailBox.

Hopefully you got my reply.

yes thank you very much

I’ve been experiencing the same issue when sending to outlook.com email addresses.
I don’t get an undeliverable message and the email doesn’t hit the outloook.com spam folder, it just never arrives.
I’ve also tried sending the mail from multiple email addresses and multiple domains with the same result.
As soon as you add the email address to the “Safe Sender” list in the outlook.com account, all of a sudden, everything goes through fine to the inbox.

I’ve tried sending mail from other services to the same outlook.com mail account and they go through ok.

I can only assume there’s something about the setup of the mail-in-a-box server that outlook.com (and by the sounds of it, other mail services) doesn’t like.

As I said above, it could also be your IP address, your ISP, or your domain name that the recipient doesn’t like.

What cloud provider are you using for the machine?

I’m using Digital Ocean.
Whilst I agree it could be the IP, I don’t think it’s the domain or the ISP. As I said, I tried sending mail from other accounts that are not hosted on the MIAB server but using the same ISP and they got through fine, likewise, before I transferred the domain over to my MIAB server I never encountered the same problem.
I have also done a blacklist check using MXtoolbox and it shows up ok on all checked services.

I’m not saying there’s an inherent problem with the MIAB, because the majority of mail gets through without a problem, but there’s obviously something a small number of email providers don’t like about these emails, and I’d love to be able to get to the bottom of what it is, but I’m just not sure how else to do it.

Yeah, I agree. These things are terrible to figure out. It could be any policy on the receiving side.

You may want to check your emails against http://isnotspam.com/

It will double check your SPF, domain key and DKIM settings.

What is the size of your droplet (RAM specifically)?