Relay outgoing Mail

Hello,
On the new OS X Server 3.0 when selecting 'Relay Outgoing Mail through ISP' and entering example.com:587 the Server App complains and rejects the entry as invalid.
Works fine on OS X Server 2.2.2
Any suggestions/help will be greatly appreciated.
Thanks,
Michael A.

I have the same problem when i do vi and port then restart mail service i get these problems
Oct 30 09:44:30 tarfan.net postfix/master[3206]: fatal: bad string length 0 < 1: setgid_group =
Oct 30 09:44:41 tarfan.net postfix/master[3229]: fatal: bad string length 0 < 1: setgid_group =
Oct 30 09:44:51 tarfan.net postfix/master[3252]: fatal: bad string length 0 < 1: setgid_group =
Oct 30 16:06:55 tarfan.net postfix/postmap[2544]: fatal: bad string length 0 < 1: mydomain_fallback =
Oct 30 16:06:56 tarfan.net postfix/postmap[2546]: fatal: bad string length 0 < 1: mydomain_fallback =
Oct 30 16:07:09 tarfan.net postfix/postmap[2559]: fatal: bad string length 0 < 1: mydomain_fallback =
Oct 30 16:07:10 tarfan.net postfix/postmap[2563]: fatal: bad string length 0 < 1: mydomain_fallback =
Oct 30 16:08:53 tarfan.net postfix/postmap[2666]: fatal: bad string length 0 < 1: mydomain_fallback =
Oct 30 16:08:54 tarfan.net postfix/postmap[2672]: fatal: bad string length 0 < 1: mydomain_fallback =
Help please not using setgid and have localhost as backup domain can some give me example of what my main .cf file should look like
Thans

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Relaying Outgoing Mail Doesn't seem to work

Hi,
I am a subscriber to Comcast ): and because many mail servers reject my mail from a non-static IP address, I use the option under Server Admin - Mail called "Relay outgoing mail through host: smtp.comcast.net
However this doesn't seem to help. In fact looking at the header of a message I sent from my server to a gmail account, it shows the IPs as my personal ones:
X-Gmail-Received: ed39f49809ec13d0902a5c7b1af1634eb8efbed3
Delivered-To: [email protected]
Received: by 10.65.185.3 with SMTP id m3cs10855qbp;
Wed, 18 Jan 2006 18:24:40 -0800 (PST)
Received: by 10.65.123.16 with SMTP id a16mr12352qbn;
Wed, 18 Jan 2006 18:24:40 -0800 (PST)
Return-Path: <[email protected]>
Received: from empco.org (pcp04542035pcs.brmngh01.mi.comcast.net [68.41.167.143])
by mx.gmail.com with ESMTP id e16si240582qbe.2006.01.18.18.24.39;
Wed, 18 Jan 2006 18:24:40 -0800 (PST)
Received-SPF: neutral (gmail.com: 68.41.167.143 is neither permitted nor denied by best guess record for domain of [email protected])
Received: from localhost (localhost [127.0.0.1])
by empco.org (Postfix) with ESMTP id B3E3E110147
for <[email protected]>; Wed, 18 Jan 2006 21:24:38 -0500 (EST)
Received: from empco.org ([127.0.0.1])
by localhost (empco.local [127.0.0.1]) (amavisd-new, port 10024) with ESMTP
id 00342-02 for <[email protected]>; Wed, 18 Jan 2006 21:24:29 -0500 (EST)
Received: from [127.0.0.1] (localhost [127.0.0.1])
by empco.org (Postfix) with ESMTP id 9CC46110129
for <[email protected]>; Wed, 18 Jan 2006 21:24:28 -0500 (EST)
Mime-Version: 1.0 (Apple Message framework v746.2)
Content-Transfer-Encoding: 7bit
Message-Id: <[email protected]>
Content-Type: text/plain; charset=US-ASCII; format=flowed
To: [email protected]
From: James <[email protected]>
Subject: test
Date: Wed, 18 Jan 2006 21:24:26 -0500
X-Mailer: Apple Mail (2.746.2)
X-Virus-Scanned: by amavisd-new at empco.org
test
How can I get this working so all server like AOL accept my mail?

#relayhost = $mydomain
#relayhost = [gateway.my.domain]
relayhost = smtp.comcast.net
#relayhost = uucphost
#relayhost = [an.ip.add.ress]
# REJECTING UNKNOWN RELAY USERS
then i did this:
empco:~ james$ grep /etc/postfix/main.cf relayhost
grep: relayhost: No such file or directory
Couple of things...
1. Sorry, I got the grep command wrong way round! It should be...
grep relayhost /etc/postfix/main.cf
All it does is show the lines in the file which contains "relayhost" - easier than listing the whole file.
2. The GUI normally adds the options at the end of the file - so if grep lists another 'blank' relayhost, remark out your old one and edit the entry at the end. (just in case an existing blank entry at the end is overwriting your edited one).
3. You can actually edit main.cf whilst the mail services are running. Just execute the reload command in Terminal afterwards...
sudo postfix reload
The sudo prefix runs the command as root, so it will ask for the root (admin) password.
Any changes made like this should automatically show up in the Server Admin GUI. Click the 'refresh' button.
I've confirmed the above works on my test system, so here's hoping!
-david

Relay Outgoing Mail Through Host Not Updating

We relay our mail through an external company and I have added the entry to Relay Outgoing Mail Through Host field and enabled the tick box. What ever I do I cannot get these changes to take affect. I have tried modifying the main.cf and enabled the relay option without any joy. After modifying these I performed a full restart but it still hasn't taken affect.
This has been working up to now but after a power cut stopped for some reason.
We are running Mac OS X Server 10.4.8.
Thanks
Ross

I'd noticed a small glitch with the GUI during earlier testing. Might not clear things for you but worth trying...
Set it with the Relay Outgoing Mail ticked and relay server entered - click Save.
Wait for whirling update thingy to stop.
Delete the relay server name then tab out of field (field fills with greyed out "relay.example.com"), only then untick the option - Save.
Wait for whirling update thingy to stop.
Tick the option, fill in the relay server - Save.
If no change, people will probably need the unedited output from "postconf -n" and an example mail.log entry showing an outgoing message leaving the server.
-david

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!

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.

I cannot send outgoing mail because it is rejected by the server because it doent allow relaying

I cannot send outgoing mail because it is rejected by the server because it doent allow relaying

Go into Settings>Mail, Contacts, Calendars>your account>Outgoing mail Server SMTP>Primary Server then turn Server ON and fill in both User Name +Password under Outgoing Mail Server.

Outgoing mail server setup

Hello everyone,
I am having problems with setting up the e-mail response.
How do you authenticate the smtp server from FCS?
In the outgoing mail server, I put "smtp.broadband.myISPprovider.com" - string I got from them. There is nowhere in FCS to put user name and password for authentication.
The e-mail response does not even show in the "View All jobs" window like every other response.
I tried every flavor of the string, including the port :587 , my e-mail address and such with no luck.
What am I missing?
If anyone could help, please.
Thanks
Radek

Thanks Simon,
I've just spoken to Apple and sure enough, the outgoing mail needs to go through an open relay server for it to work. Well..., open relay servers are getting blacklisted by most ISPs because of all the spam. I also spoke to my ISP and they do not offer any open relay so I'm stuck. I don't want to leave our system vulnerable by going through some shady open mail server. Apple needs to figure out how to make the authentication possible from FCS.
Thanks again
Radek

Load balancing outgoing mail with 3 outgoing servers

We are trying to balance our mail out with 3 separate mail servers from our incoming server. Our organization sends alot of mail and we wanted to balance it with 3 outgoing SMTP servers. We have them all working, in the zone for the primary DNS and incoming mail server. And we can get mail to go out on the three servers, BUT and this is a problem if the mail includes any messages to the network (hence the incoming server) then the SMTP servers complain they cannot find it and give a error message about not being able to connect to deliver any local mails out of the bulk mail we send. Any ideas how to get the SMTP to see the incoming mail server (which is the DNS server for network) and deliver mail to accounts on the network? Maybe we are doing something that OS X SNL server cannot do? Any ideas.
I will post the error message later but I need to leave for meeting for now.
Thanks
Russ

Here is error message we get:
Mar 17 21:34:45 mailout1 postfix/smtp[32307]: connect to mail.vineyardil.net [173.161.44.97]:25 Operation timed out
Mar 17 21:34:45 mailout1 postfix/smtp[32307]: DE90A1AF591: to =<[email protected]>, relay=none, delay=23732, delays=23701/0.01/30/0, dsn4.4.1, status=deferred (connect to mail.vineyardil.net [173.161.44.97]:25 Operation timed out)
To explain mailout1 is the first one in priority of outgoing separate SMTP servers we set up in the zone of mail.vineyardil.net which is the DNS server. They send out ok all outgoing mail to other addresses as we wanted them (rather than having mail.vineyardil.net do it) but when we send to an address with vineyardil.net on it then we get this same message.
It seems like mailout1 cannot send to the incoming server. Note the ip address it gives is the ip of the cable modem on this network not the ip address locally in the net we have.
Our MX records all look good and things work with mail if we use it both as incoming and outgoing (SMTP) but when we use the secondary servers for outgoing they seem to not be able to send to this server. Is there something we should look for?
Is SL server not capable of what we are trying? Any feedback would be most appreciated. We would like to really use this setup as I explained to do load balancing of mail as part of our attempt on this new network to get our bulk mailing split up between the 3 outgoing servers so we will not be labeled spam by the security systems out there these days like it was on our old network.
Thanks for your time.
Russ Jacobson

How do I get the server to relay outgoing message?

When I try to send an e-mail I receive a message that the server does not allow relaying. How do I fix this?

Try going into Settings > Mail, Contacts, Calendars > select the account > account name , tap on SMTP (under the 'Outgoing Mail Server' heading) and then tap on your Primary Server and try entering your email account and password and see if it then works

Ironport C170 Relay outgoing Email to External Server

We have a new Ironport C170 and am only using the appliance for Encryption/DLP. We wish to have incoming and outgoing Email to flow through this appliance. All incoming Email will be relayed to our Exchange Server and all outgoing Email will be relayed to our SAAS Email Filtering System for processing and delivery. The incoming part I believe is configured correctly but am having issues figuring out how to relay all outgoing to a specific domain in the cloud.
Any assistance would be greatly welcomed,
Stephen

Hi Stephen,
You can control all the outgoing mail from SMTP Route configuration, if is in GUI menu > Netowork > SMTP Route.
You can define the route to next hop based on destination domain, as for default - all other domains (this is the one that goes to SaaS) you can enter your cloud SMTP address and the port number there.
Hope this helps.
Thanks,
Donny

SMTP Outgoing Mail Server does not use password so I can not send mail..

Hi All
Can anyone help me with this?
My POP email accounts on Hosting.365.ie do not use a password to authenticate outgoing mail. They rely on a prior authenticated download to enable the outgoing mail server.
On my MacBook Pro there is an option in the SMTP server settings under authentication for "none' and all my accounts work perfectly on the MacBook.
However my iPhone4 (brand new) and iPad (both up to date) there is no option under the SMTP server settings for "none". I think this is the root of the problem. Has anyone else come across this or is there a workaround?
Many thanks if anyone has any insights.
Peter

Yeah, I don't know why the difference. Interestingly for me, the iOS version in iOS4.2 is "better" than the OSX version of Mail because now I can have more than one Exchange account.
I am sympathetic with your need to separate your lives. I have a client that accidentally got one of my alternate email addresses and cannot/will not update his address book with the "correct" address, despite my requesting several times over the course of a year. In any case, I don't think there is any way around this other than completely changing your email address. (If not a second Gmail, then Yahoo, Hotmail or other email provider.)
The only time I've ever seen a "no password" SMTP server was as I previously said, it used a "network authentication" method. Many, many moons ago, SMTP servers often didn't have password authentication so would often be used for spam relaying. Before mobile users, "network authentication" by ISPs was fine since they could figure out which user was spamming since they could trace the IP addr, MAC addr, etc back through the physical link to the user. But with mobile users who change networks constantly, the general trend was to password authentication, even for wired ISPs since their users would want to have access to send mail while away from home. (e.g.: you're a RoadRunner customer, but want to send mail while using your laptop on vacation in Italy.) This "prior authenticated download" I've never heard of anyone else doing.

Outgoing Mail Problem on iPad and iPhone

I have a Telstra iPhone and iPad. When I try to send or relay emails from work or other locations (not at home) to my work email or to other people I get the following message: Cannot Send Mail. A Copy has been placed in your Outbox. The recipient xxxxxx was rejected by the server because it does not allow relaying When I am at home and connected via wifi to my optusnet account, I can usually send emails from my iPad, but not always from my iPhone. Very frustrating!

Hi sgn,
Please ensure you have the correct settings by following our guide here:
https://support.telstra.com.au/t5/Email/ct-p/LSP_Email#item-ARTICLES-LSP_Email-399836
I'm assuming this is a Bigpond email address?If so it will be best to follow the heading: Set up Telstra email on the BigPond® platform, on your tablet or mobile
If you continue to have problems it may be due to network you're connected to at the time restricting this. You may need to use the outgoing mail server of the provider that you're connected to via Wi-Fi. If the email isn't large you can toggle on Mobile data to send if this suits.
-Matt W

Problems with incoming and outgoing mail

I've read a number of posts on this topic, yet none completely matches the problems I'm having.
Incoming Mail:
My incoming e-mail is a pop account hosted by Earthlink. I am able to enter my data and get mail using a non wi-fi network.
Outgoing Mail:
When I use the generic AT&T outgoing server, it works, but then I am unable to get mail, and vice-versa. (I tried sending mail through the general web hosting server that Earthlink recommended (and works on my laptop when traveling away from home network, but it just spins.)
Conflict:
I am either able to send mail or receive mail, not both at once, thank-you-very-much.
The settings and ports are unchanged. And, I can't figure out why one would affect the other considering they are two completely different settings.
We're currently trying to set up a smtp.com or Google mail account, which is okay, but I would much rather solve this without any more links in the chain.
Any suggestions? Will re-setting my iPhone completely help?

Yes, thanks, was my first stop and very handy.
Unfortunately, because my pop account is hosted/relayed at Earthlink, it did not identify the account as it would a stand-alone service. I tried using the basic Earthlink account info, but of course, my basic account does not have anything to do with my current business pop account. So after using the set-up assistant, I was back at square one.
I was able to set up smtp.com successfully and am up and running.
I just can't figure out why one setting would mess up another.

Need advice to make outgoing mail work again

This has gotten too weird for me to figure out, and I'm looking for some help. It's like Mail has decided to stop sending mail. I'll explain the problem and then I can explain why it's almost certainly a problem on my end.
Any mail I send gives me error messages.
If I use my company's server, I get the message:
Cannot send message using the server mail.mydomain.us
The server response was: sorry, that domain isn't allowed to be relayed thru this MTA (#5.7.1)
Use the pop-up menu below to try a different outgoing mail server. All messages will use this server until you quit Mail or change your network settings.
If I try to use my Roadrunner server, I get
Cannot send message using the server smtp-server.houston.rr.com
Use the pop-up menu ...
If my wife sends mail using Mail from her machine, using our company server, it goes through.
I can receive mail via both mail servers, no problem.
If I go to the web interface for my server, I can send and receive.
The last note I was able to send (from my domain) was Sunday night at 10:16 pm. The first message I tried to send the next morning, I got this error. No Mail settings were changed. No network settings were changed -- I know, that makes it sounds like it can't be a Mail problem, but I don't know what other choices I have.
I've logged off and back on with no change. I've rebooted the machine with no change.

Are you also unable to send messages via your RR email account using RR's SMTP server?
Is your company's SMTP server authenticated?
Are you using 25 for the Server Port with your company's SMTP server and if so, have you tried changing the server port from 25 to 587?
FYI - sending messages via webmail access using a browser is not done with an SMTP server as is required when sending messages with an email client such as the Mail application so this is not related.
Do you have any SMTP servers available with Mail that are not being actively used by any email account?
I am also a RR customer and I use RR's SMTP server to send messages with my .Mac account when connected to the internet at home via RR with no problems.

JavaMail Problem with Outgoing Mail

Hi, I's using a J2EE web application that makes use of JavaMail and an SMTP mail server to send outgoing mails and POP3 mail server to recieve mails.
Everything is going fine with the POP3 mail server the application is able to recieve mails, and parse them.
But I have problem with the outgoing mails, The application is successfuly sending mails through the SMTP mail server to addresses inside my organization, but failing the relay them to external addresses.
Example: The application is successfuly sending mails to [email protected], but failing sendimg mails to [email protected]
PS: the Address I configured the application to send emails from, can send mails to external users.
I'm using Microsoft Exchange Server.

Yeah man, I know. But the thing is am not familiar
with the Microsoft Exchange Server configuration. And
I guess my problem is a configureation problem.Then maybe a Java forum isn't the best place to be looking for help, innit? :-)
Any
expertise with Exchange Server ?Somewhere between "zero" and "none whatsoever."

Relay outgoing Mail

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