Mavericks Server mail relay custom port

After upgrading to Mavericks i cannot enter a custom port in the mail relay section of the Mail Service
in older versions i could enter: mail.domain.com:587, but now i cannot save this setting.
Anyone an idea how to fix this ?
Thanks in advance

It is about the mail service in OS10.9 SERVER I presume.
I got the same problem.
Via the terminal I was able to set anther portnumber (port 26) instead of standard port 25.
Now I can have mail sent via a script I have running om my website, BUT
only mails to my own domain are sent.
All other mailaddresses do not get my script-generated mails.
Same config on OSX10.8 server2 works fine, it went wrong after upgrading to OSX10.9 Server 3.
what can I do?

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OS X Server 3 outgoing mail relay no longer supports a specific port

Just installed OS X Server 3 on Mavericks. All is well, but for some reason it does not allow adding a specific port for "Outgoing mail relay: mailout.isp.com:587"
OS X Server 2 used to allow this and i used it to connect to my smtp relay from my isp. It does not allow port 25 connections. If you try this in OS X Server 3 it just complains with "bad formatting"
Can anyone confirm this?

Found another thread discussing this.
https://discussions.apple.com/message/23544605#23544605
Answer from there:
You need to edit the postfix main.cf file manually with your favorite text editor:
sudo vi /Library/Server/Mail/Config/postfix/main.cf
find the line
relayhost = host.example.com
change it to
relayhost = host.example.com:587 (or some other port)
then do a
sudo postfix reload
to reload postfix configuration files
and
sudo postsuper -r ALL
to retry sending the e-mails again.
NOTE: If you open OS X Server 3 app and go to Mail -> Relay outgoing mail through ISP -> Edit the Outgoing server address will show as BLANK, this is normal, just click cancel and leave it alone.

How do I install stunnel on Yosemite server 4 so my mail relay works on port 465?

My ISP blocks outbound smtp mail and insists I point to their relay server on port 465. After I set up mail relaying in the server config app I get SMTP log errors saying it's unimplemented. After some research it looks like I need to install a SSL tunnel package called stunnel. Has anyone had an success getting stunnel installed? Or, has anyone had any luck using Yosemite Server 4 to mail relay through verizon.net (port 465)? Any suggestions are much appreciated.

I'll assume that you have to authenticate to the mail relay with a name and password. The Server GUI doesn't provide for this use case.
Take the following steps to configure Postfix to relay mail to a remote SMTP server with password authentication over SSL. Substitute as required for strings in italics below. Address is the fully-qualified domain name of the relay host. The value of port is usually either 25, 465, or 587. Username and password refer to your credentials on the relay host.
In the current version of OS X Server (but not necessarily in older versions), Steps 1 and 3 should be done for you when you enable relaying and relay authentication in the Server application.
1. If necessary, create or update the relayhost directive in
     /Library/Server/Mail/Config/postfix/main.cf
It should look like this:
     relayhost = [address]:port
2. Add these lines, above the section at the end that begins with the comment "# Mac OS X Server":
     smtp_sasl_security_options =
     smtp_tls_CAfile = /etc/certificates/relayhost.pem
     smtp_tls_session_cache_database = btree:$data_directory/smtp_tls_session_cache
     smtp_use_tls = yes
3. If it doesn't already exist, create the password file
     /Library/Server/Mail/Config/postfix/sasl/passwd
with this content:
     [address]:port
     username:password
Here address must match $relayhost.
Then create the password database:
sudo postmap /Library/Server/Mail/Config/postfix/sasl/passwd
This action creates the file
     /Library/Server/Mail/Config/postfix/sasl/passwd.db
The two password files should be readable by root only.
4. Create the file
     /etc/certificates/relayhost.pem
with the CA certificate(s) to be trusted for authentication of the remote host. You get those certificates from the service provider. If you can't find a link to download them, try this:
openssl s_client -connect address:port -showcerts < /dev/null | sed -n '/-BEGIN /,/-END /p' | sudo sh -c 'cat > /etc/certificates/relayhost.pem'
The command may produce an error message that isn't necessarily significant. For servers that use the older STARTTLS protocol, rather than straight TLS or SSL, this command may need to be modified.
5. Restart the Mail service.

Mail relay server specifying a port...

Hi,
The advanced server guide says you should be anle to specify a port .. ie.. myserver:587 in the dialog box.
Dialog box says Formatting error invalid value.
I use the Dyn mailforwarding service .. or i did till the latest upgrade broke it.
Does anyone know of a fix? .. I assume it will mean editing the postfix files .. that no doubt the next upgrade will break again.
Thanks in advance.

You have to edit the configuration using the command line; Server.app lost the ability to handle the outbound SMTP relay otherwise.
sudo serveradmin settings mail
You're after the relayhost setting (the following is from a generic setup, you'll want to set the host name via the GUI then check the output here, and add the port to the relayhost specification:
$ sudo serveradmin settings mail | grep -i relay
mail:postfix:smtp_auth_relay_dict:smtp_auth_relay_userid = ""
mail:postfix:smtp_auth_relay_dict:smtp_auth_relay_pwd = ""
mail:postfix:smtp_auth_relay_dict:smtp_auth_relay_host = ""
mail:postfix:luser_relay_enabled = no
mail:postfix:relayhost = ""
mail:postfix:relayhost_enabled = no
mail:imap:lmtp_luser_relay_enabled = no
mail:imap:lmtp_luser_relay = ""
$
Once edited, you'll end up with something like this:
mail:postfix:relayhost = "mail.example.com:587"
Where you've entered your relay host and port. See this thread (for the Postfix-level path to this data and for some background, I'd generally use serveradmin here and not the Postfix-level access) and see this Krypted article for some more details on the setup and commands available here.
You can use postconf -n /Library/Server/Mail/Config/postfix to verify that the changes have been implemented, and here's a similar discussion of the lower-level path into this same general area.

Server App: Outgoing Mail Relay not working

Hi,
I'm trying to set up Outgoing Mail Relay on my Mountain Lion Server, but I always get bounced emails:
Oct 1 04:33:34 my.server.private postfix/smtp[9582]: C855DCE700D: to=<[email protected]>, relay=mx2.sub5.homie.mail.dreamhost.com[208.113.200.128]:25, delay=0.91, delays=0/0.02/0.65/0.24, dsn=5.7.1, status=bounced (host mx2.sub5.homie.mail.dreamhost.com[208.113.200.128] said: 554 5.7.1 Service unavailable; Client host [myIP] blocked using zen.dnsbl; http://www.spamhaus.org/query/bl?ip=myIP (in reply to RCPT TO command))
If I use in the SMTP servers list of Mail app, the exact same account credentials, the email is been delivered only when using SSL. So, I tried adding :465 and :587 to the ougoing relay server in the Server app (Relay outgoing mail throught ISP), but I get the following error and the message stays queued:
Oct 1 04:13:41 my.server.private postfix/smtp[8920]: connect to mx2.sub5.homie.mail.dreamhost.com[208.113.200.128]:587: Connection refused
Oct 1 04:13:41 my.server.private postfix/smtp[8920]: connect to mx1.sub5.homie.mail.dreamhost.com[208.113.200.127]:587: Connection refused
Oct 1 04:13:41 my.server.private postfix/smtp[8920]: 0BAD1CE6340: to=<[email protected]>, relay=none, delay=369, delays=369/0.02/0.43/0, dsn=4.4.1, status=deferred (connect to mx1.sub5.homie.mail.dreamhost.com[208.113.200.127]:587: Connection refused)
It seems I'm missing something. I want to use smtp account to send all the email coming from my Mac OS X Server, but it looks like I'm doing something wrong or the Server App doesnt work the same way Mail App does when connecting to a SMTP server.
Any comments?

Let me add....
Mail app is connecting and sending the emails correctly with the same credentials but using SSL through port 25:
READ Oct 01 05:04:01.566 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:my.externalrelayserver.net -- port:25 -- socket:0x7f890be0c620 -- thread:0x7f890ca3dd70
250-homiemail-a45.g.dreamhost.com
250-PIPELINING
250-SIZE 40960000
250-ETRN
250-AUTH PLAIN LOGIN
250-AUTH=PLAIN LOGIN
250-ENHANCEDSTATUSCODES
250 8BITMIME
WROTE Oct 01 05:04:01.588 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:my.externalrelayserver.net -- port:25 -- socket:0x7f890be0c620 -- thread:0x7f890ca3dd70
AUTH PLAIN (*** 48 bytes hidden ***)
READ Oct 01 05:04:01.793 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:my.externalrelayserver.net -- port:25 -- socket:0x7f890be0c620 -- thread:0x7f890ca3dd70
235 2.7.0 Authentication successful
I would like to force Server App to do a SSL connection to port 25 of the specified relay server, but not sure how to do this. If I don't manage to do SSL on port 25, then, my relay server will bounce the emails...
grrrr!

Mail changes "Use custom port:" to 587

I have set Mail to use SMTP port 25 "Outgoing Mail Server (SMTP)->Edit SMTP server list...->Advanced->Use custom port: 25"
Restarting Mail doesn't effect the setting, but if I restart the system it will change that custom setting to 587. Why?
Anyone else having this problem?

I was having this problem too. I ended up rebuilding my user account, and then my mail accounts, from scratch. The problem, and several others, are gone now.
I am testing SL on two other computers and one of them is having the problem -- Mail forgets to use port 25 for SMTP.

Yosemite Server Mail and Google Domain Relay

I want to simply use the server to send automated emails from scripts. I have server installed. Over the course of two days I've have followed several posts:
http://www.anujgakhar.com/2011/12/09/using-macosx-lion-command-line-mail-with-gm ail-as-smtp/
http://blog.anupamsg.me/2012/02/14/enabling-postfix-for-outbound-relay-via-gmail -on-os-x-lion-11/
And the updated Yosemite version here:
http://blog.anupamsg.me/2013/12/22/enabling-postfix-on-osx-as-a-relay-revisited/
Yosemite Server configuration
http://krypted.com/mac-security/configure-the-os-x-yosemite-server-mail-service/
I've gotten no where. In my last attempt all sasl errors and no mech connections had stopped but mail did not appear to go anywhere. No trace. I stumbled across a post that said ssl connections from Mac OS X Yosemite are broken and just don't work.
Now the real rub. I have gotten the same thing working with Linux in 5 minutes following this post:
https://rtcamp.com/tutorials/linux/ubuntu-postfix-gmail-smtp/
Then within an hour my crontab and scripts were written, debugged, and blissfully sending email.
I would rather run this from my Mac server. I understand that this may become an in-depth discussion/debug session (remember the old sendmail.cf day?!) and would greatly appreciate someone's mentoring here.
-Tim

Hi,
maybe it helps or not, I solve a other performance problem which is more related to the mailbox speed but this error on client side is gone afterwards:
In Yosemite there is still also a problem with the automatic settings detection in Mail.
That means that the application try's to find a working authentication mechanism in combination with different ports and encryption.
So far so good, this feature would be okay but the application never stops to do that. So we are shortly connected but the connection becomes invalid again.
This leads to performance issues and the application becomes very slow!
If you refer your client log file maybe you can see some "Failed to start the SASL connection" issues (coming from Mail.app).
In case that you are running a OS X Server which is used by Mail you will see in /var/log/mail* /Library/Logs/mail* various login failures. In case that you have enabled the Adaptive Firewall it can be happen that your IP is blocked for 15 minutes.
Of course this must not be a issue for everyone I believe it strongly depends on your email server / provider which auth. stuff is supported or enabled.
To solve it:
1.) Open the Mail Preferences
2.) Goto "Accounts" and select your Provider/Account
3.) Klick Enhanced (the last right tab)
4.) Disable the automatic settings detection (first checkbox)
5.) In case you didn't enable "MailDrop"
This works in Mail 8.1 on Yosemite 10.10.1

Mail Server when Comcast blocks port 25

I want to host a mail server, and am able to get mail to send, but am unable to receive mail. I tried sending an email from my gmail, and it gets delayed because it can't connect to xxx.xxx.xxx.xxx:25. I then found out that Comcast blocks port 25. Is there a way to change what port the server app uses so it can receive mail?

This is a common question; you're not the first person to have considered resetting the SMTP TCP port.
As Strontium90 indicates, you can most certainly set up your own global mail infrastructure on a variant port (possibly even by using DNS SRV records to find the port de jour), but by the time that's all coded and debugged and generally accepted and standardized and in widespread use around the planet, Comcast and the other ISPs will probably just detect and block the new port or the new service on their residential service tiers. Which means you'll need to add TLS encryption and potentially random ports, and down the proverbial rabbit hole we go.
But seriously, the usual and preferred and best approach is a business class service, as that has port access and you can get correct DNS. Without correct forward and reverse DNS translations, many other SMTP mail servers will detect a dynamic IP service as a spam engine, and drop outbound mail as it arrives. Some mail servers will detect this and will also drop inbound mail, as well.
As an alternative to a business-class service, you can set up a mail relay through your ISP, or potentially a relay via a commercial mail relay service — if either of these approaches is permitted by your ISP terms of service. There are various folks that offer these mail hop services by subscription, but then all your mail is routed through that service and that may or may not be desirable.
Hosting your own virtual private server or dedicated host just for mail can be pretty cheap these days, if you're willing to run your mail server in a data center. That avoids all entanglements with your ISP. (But again, if you're willing to host your mail elsewhere.)

Mavericks Server Firewall Blocking e-mail

I've got mavericks server installed. DNS and mail are configured on the server, however I can't receive mail because the firewall is blocking it. How can I open port 25 on the firewall so I can receive mail? I can send mail with no problem, but I can't receive mail.

Actually I solved the issue. I thought the firewall was blocking SMTP port 25 because I used the network tool to scan the system and it kept showing the port was closed. Then I remotely logged into the computer and went to GRC.com and ran Shields Up. Shields Up showed that the port was open. After that I started going through the configurations again to see what might be the issue. I got to DNS I noticed the MX record didn't look correct. So from my computer I ran an nslookup -type=mx on the domain name that was currently in the DNS. It didn't resolve. So I updated the MX record in the DNS with the Fully Qualified Domain Name (FQDN) to see if I could at least get that to resolve. When I did that, everything started working. I left it at that and called it a day.

An error occurred while sending mail. The mail server responded: Relaying not allowed.

Suddenly I am not able to send any email from my account, from pc or phone.
It gives error message "An error occurred while sending mail. The mail server responded: Relaying not allowed. Please check the message recipient --------and try again."
I have checked account setting and is correct. please help

This message, which comes from the server, usually means that you are using an smtp server provided for use with one particular account to send messages "from" other accounts. The fact that it also happens with your phone does indicate that it is external to Thunderbird.
How many different email accounts do you have? How many different providers are involved?

Mail relay issue since lion server install

I upgraded (or not) my Mac Mini Server with Snow Leopard, to Lion Server.
I'm now getting mail relay errors when sending email to an account on my server from gmail.
"Technical details of permanent failure:
Google tried to deliver your message, but it was rejected by the recipient domain. We recommend contacting the other email provider for further information about the cause of this error. The error that the other server returned was: 554 554 5.7.1 <[email protected]>: Relay access denied (state 14)."
I'll post postconf -n if required.
voigtstr.com has an A name at the domain name registrar
mail.voigtstr.com has an mx record.
dig +short MX voigtstr.com returns
1 mail.voigtstr.com.
voigtstr.com and mail.voigtstr.com both point to my external ip address
any pointers?

LincNesh,
Seems the problem has been solved by Peter Rauen.
See this discussion: Mail relay SASL problem / postconf -n
I checked on my server and Peter is right. Although there are configs in /etc/postfix there is another path with postfix conf files: /Library/Server/Mail/Config/postfix
I actually only had to insert this line to main.cf there: smtp_sasl_security_options =
After a postfix reload my mails are being delivered via dyndns again.
Cheers!

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I want to install Oracle 10g Application Server in Port 1522 or some other port as in port 1521 Oracle 10g database server is already installed.
But every time I try to install Oracle 10g Application Server it give the warning about 1521 port and then start installing on same 1521 port automatically.
What should I do if I want to install in some other port ?
Please help
Thanx

As a method, to install an OAS on a custom port,
1) make a file called staticports.ini and define your components/ports there.
2) on the Specify Port Configuration Options screen, select Manual and specify this file.
Follow this link for details for 10g.
http://download.oracle.com/docs/cd/B14099_19/win.1012/install.1012/install/reqs.htm#CHDJACIG
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Sending external emails thru Mail relay in Lion Server

Hi,
I've setup Lion Server with a Mail Relay for outgoing emails and currently paying for x amount of emails per day.
Does Lion Server send all outgoing emails through the relay, or is it smart enough to know that internal emails (on the same subdomain) or emails generated by web apps on the server itself do not go through the relay because it can deliever it directly into the mailbox that resides on itself?
We generate a lot of emails internally, but only a handful to external addresses.
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Please let me know.
Thanks!

The mail server first checks the domain of any recipient. If it's a local domain (i.e. one that the server handles) then it just passes that message to the user's mailbox.
It's only non-local domains that need passing upstream through your relay, so you can send as many internal emails as you like - they won't touch your relay server.

ML server: more than one mail relay

How can I add more than one mail relay for outgoing mail through ISP?
In the server.app I can only add one mail-relay. My ISP recommends more

First I've heard of that recommendation....
Unless there's something rather odd going on here — cases such as very flaky ISP mail servers or very flaky network connections to the mail servers, such that you're finding a need to redirect your own mail client host settings to different mail servers at the same ISP, for instance — or if you're going to be sending out massive volumes of mail — I would leave it at one host, and see if there's an issue.
Mail servers are designed to retry for transient outages, so most errors should retry.
Postfix allows one relayhost, unless you want to get into sender_dependent_relayhost_maps and that's not particularly common.
With static IP and correct DNS, you could eliminate the relayhost setting entirely. That's a typical approach with mail servers.

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http://jonathanhult.com/intradoc-api/intradoc/shared/SharedObjects.html
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Mavericks Server mail relay custom port

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