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Sendmail Enabler for Mac OS X

gulker writes "It's really nice to be able to use sendmail as a SMTP server on a PowerBook if you move around a lot. But enabling sendmail on OS X is non-trivial, and while a good tutorial exists, the stock Mac OS X 10.2 package is missing the m4 macro processor needed to regenerate sendmail.cf. So it was great news to hear about Bernard Teo's Sendmail Enabler, a cool Aqua-GUI-interface sendmail 'configurator' for Mac OS X."

27 of 88 comments (clear)

  1. Sendmail?! by justinkim · · Score: 5, Informative

    Just install postfix instead. Secure, easy to set up, right there in Fink. What's not to like?

    1. Re:Sendmail?! by Mikey-San · · Score: 4, Insightful

      If anything, Sendmail is less secure than Postfix, bro. And not part of the OS? Well, get ready for Postfix, 'cause it's in Panther in the place of Sendmail. ;-)

      --
      Mikey-San
      Karma: +Eleventy billion (mostly affected by watching Celebrity Jeopardy)
    2. Re:Sendmail?! by EvilDrew · · Score: 5, Informative

      You'll get your wish. The developers release of 10.3 (Panther) uses Postfix by default.

    3. Re:Sendmail?! by sporty · · Score: 3, Insightful

      The fact it's not sendmail.

      It's the case of software once being buggy now being deemed always buggy.

      Remember the various bugs with ext3? Well, let's use the same idea. Ext3 will never be as stable as ext2, especially since it corrupts file systems.

      Or apple. Apple never will make a fast system, since they always lag behind intel.

      Can't we get past these childish prejiduces? Sendmail is pretty friggin cool. At least in sendmail, i can analyze the headers of a message, and if certain ones are present, do one thing vs another. And I don't need a third party util, like procmail to do it.

      --

      -
      ping -f 255.255.255.255 # if only

    4. Re:Sendmail?! by hobbit · · Score: 4, Funny


      At least in sendmail, i can analyze the headers of a message, and if certain ones are present, do one thing vs another. And I don't need a third party util, like procmail to do it.

      Are you kidding? Do you not understand the unix philosophy of "do one thing, and do it well"?

      --
      "Wise men talk because they have something to say; fools, because they have to say something" - Plato
    5. Re:Sendmail?! by Arthur_5150 · · Score: 2, Informative

      > Well, get ready for Postfix, 'cause it's in Panther in the place of Sendmail I am using qmail since 2 years and i like it, what's difference with postfix ?

    6. Re:Sendmail?! by sporty · · Score: 4, Insightful

      No, I'm not kidding. If we seperated every single piece, you can suffer what some DB schema's suffer from, over normalization. qmail REALLY suffers from this in its goal of security.

      If qmail for instance, since spamassassin doesn't know a thing about the mail system in front of it, it can't tell qmail not to bounce a message from a spammer.. nor can qmail figure this out. So now it bounces mail and then when it can't reach the spamemr, it bounced to postmaster. Joy.

      I understand the philosophy of "do one thing and do it well". Do you understand trying to spread yourself too thin? Ever take a look at the redhat configuration scripts? THAT is spreading all of the functionality over too many things, that it is convoluded.

      So let sendmail do what it does well.. process mail. Just so long as it doesn't try to do ftp and my other services as well.

      --

      -
      ping -f 255.255.255.255 # if only

    7. Re:Sendmail?! by davids-world.com · · Score: 5, Informative
      Sendmail crashed / stalled / left-to-walk-the-dog all the time on the powerbook, needed to be rebooted. Sometimes I didn't notice and my outgoing email stayed in the outgoing queue for days.

      After I installed Postfix, everything works like a breeze. Installing Postfix is quite simple -- because there are one or two pitfalls, I wrote a short step-by-step tutorial.

    8. Re:Sendmail?! by snero3 · · Score: 2, Insightful

      I agree with you, Sendmail is extremly powerful if you know how to use it properly IE understand the config file.

      That being said, not a lot of people really understand the config file at all (thus leaving open email relays for spammers etc) where as postfix, although not as powerful, is a hell of a lot easier to configure. Most people I know swap out sendmail for postfix becuase they can use all of the features of postfix and none of the features of sendmail(or very few).

      What is the point of having really powerful software if you are unable to use it.

      --
      It said "windows 98 or better" so I installed Linux
    9. Re:Sendmail?! by SewersOfRivendell · · Score: 4, Funny
      It's the case of software once being buggy now being deemed always buggy.

      Please. Sendmail has been providing remote root since 1983 and continues to do so. Just using Google should be enough to scare you away from it.

    10. Re:Sendmail?! by __past__ · · Score: 2, Informative

      No, but unlike qmail, it is Free Software.

  2. Why sendmail is good for Apple servers by Nightlily · · Score: 5, Insightful

    I'm happy to hear some allowed us to enable Sendmail. I know there are other SMTP servers out there (Postfix), but Sendmail is not a horrible mail server. Yes, there are bugs (any product that is used will have bugs reported eventually). Now, Exchange server.... that's a horrible mail server.

    The best part about this news is that it gives Mac users more options. Regardless if you like a project or not, the ability to choose between server products helps advance the Apple server platform.

    1. Re:Why sendmail is good for Apple servers by sid+crimson · · Score: 4, Insightful

      Repeat after me: Exchange is not a mail server, it's a Groupware package.

      Anyone using it strictly for mail deserves what they get. The rest of us deserve... well... erm. Nevermind. :-)

      -sid

  3. It also might not work.. by mmontano · · Score: 3, Interesting
    Turning your own computer into a sendmail server only works if the recipient server trusts you and your machine.

    A machine attached to a dial-up Earthlink account that is trying to sendmail through to an AOL email account looks a lot like a setup for spam.

    As a result, many SMTP servers won't accept SMTP connections from unknown SMTP servers attached to unknown networks.

    (I used to have a similar setup on my PB and used a variety of dial-up/wi-fi internet access and it rarely worked. I setup a private secure SMTP server for me and my friends and it works great.)

    1. Re:It also might not work.. by mmontano · · Score: 5, Interesting
      I've set up a private SMTP server that's attached to a cable-modem and it works flawlessy, yet my Internet IP address is dynamically assigned through DHCP.

      For the major dial-up networks, JoiNet/UUNET/NetZero/EarthLink and so on, they probably assign an advertised (and therefore known) block of IP addresses to dial-up connections.

      There are numerous settings in postmail/sendmail/qmail etc that control who can send mail through SMTP servers. From experience, many of these are enabled to prevent 'random' SMTP servers from relaying mail through them.

      That's why I feel the Sendmail Enabler for Mac OS X could not be the magic elixir that it is tempting to make out of it.

    2. Re:It also might not work.. by PoiBoy · · Score: 4, Informative
      I have an SMTP server running on my cable modem, too, with a dynamic address. For the most part, it does work flawlessly.

      However, some ISP's, notably AOL, no longer accept mail from dynamic IP addresses. Whenever I try and send email to an AOL address, it gets bounced back to me.

      Of course, I could just relay my mail through my cable company's SMTP server, but this is a good excuse for me to not send email to AOL users.

      --
      Sig (appended to the end of comments you post, 120 chars)
    3. Re:It also might not work.. by diverman · · Score: 5, Interesting

      I have been running an SMTP server from my house for a number of years now. Few (if any) mail servers are configured to block delivery from a "suspicious" hostname/address.

      The way it works is that a mail server will only allow relaying (sending mail to a user that that particular server doesn't manage) from a source address that is within it's network/subnet (or other allowed subnets). A server almost always accepts a connection for email to be delivered to an address that it handles (ie. where it's the end of the line).

      Running sendmail (or other SMTP servers) on your local machine will only enable you to queue up your mail. Sendmail (by default configurations) does not attempt to relay the mail through another server. It tries to go directly to the mail server responsible for handling the mail. Essentially, you would have your local sendmail only allow relaying from your local host (or other home machines), and the sendmail server would deliver it to where it has to go.

      THese are not likely to be blocked because they are on dialup. Few people put a system in place that it going to try and "determine" if it's a dynamic or dialup IP address. There's no real way for the sendmail server to know, unless it subscribes to a maintained list. And that would likely result in many failed deliveries, as many lists are not terribly accurate (I've dealt with some for other purposes).

      So, if it doesn't work, it will be for a small minority or emails to be delivered.

      So, maybe you did something wrong. Maybe you had open relaying enabled. THAT is something mail servers will refuse connections for.

      Just my $0.02 on a post I think was mod'd up too much. :)

      -Alex

    4. Re:It also might not work.. by good+soldier+svejk · · Score: 3, Informative
      So, maybe you did something wrong. Maybe you had open relaying enabled. THAT is something mail servers will refuse connections for.
      Actually, AOL has recently started refusing mail from other ISP's adresses (other than their designated relays). here is an example bounce message.

      The original message was received at Fri, 25 Jul 2003 00:47:16 -0400 (EDT) from localhost [127.0.0.1]

      ----- The following addresses had permanent fatal errors -----
      ****@aol.com
      (reason: 554- (RTR:BB) The IP address you are using to connect to AOL is a dynamic )

      ----- Transcript of session follows -----
      ... while talking to mailin-03.mx.aol.com 554- (RTR:BB) The IP address you are using to connect to AOL is a dynamic
      554- (residential) IP address. AOL will not accept future e-mail transactions
      554- from this IP address until your ISP removes this IP address from its list
      554- of dynamic (residential) IP addresses. For additional information,
      554 please visit http://postmaster.info.aol.com.
      --
      It is cowardly, and a betrayal of whatever it means to be a Jew, to act as a white man

      -James Baldwin
  4. RIP: Sendmail by Znonymous+Coward · · Score: 2, Funny

    Just as vsftpd is to wuftpd...
    Postfix is to sendmail...
    Ashes to ashes, dust to dust.

    --

    Karma: The shiznight, mostly because I am the Drizzle.

  5. actually, m4(1) is in the Developer Tools by Rich_Morin · · Score: 5, Informative

    ... but you'd still need to grab the Sendmail-specific macro files and such.

    --
    Technical editing and writing, programming, and web development
  6. What about Exim? by Anonymous Coward · · Score: 4, Interesting

    I think exim is the best SMTP server for laptops, because it uses very little resources, is a snap to install, and is still highly configurable and very powerful. I use it on my PB12, and I'm very happy with it.

  7. Re:Spam Relay Enabler maybe by good+soldier+svejk · · Score: 5, Informative
    It's really nice to be able to use sendmail as a SMTP server on a PowerBook if you move around a lot

    No, it isn't.

    How about, "I want to send out 15 million spams a day for my home based internet business, but I own a mac, what can I do?"

    Seriously, you don't need sendmail to send out your email. That's what mail.app is for. Well, if you're not spammer, that is.
    Yes it is. Just add,

    DAEMON_OPTIONS(`Port=smtp,Addr=127.0.0.1, Name=MTA')

    to the m4 file before generating your .cf. That will make sendmail listen only on the loopback address. Then you can point Mail.app at your loopback address and relay from any physical location without any fear of becoming a spam relay. This solves problems for me. At work we don't allow external relaying. Likewise comcast won't let me relay from work. But I can relay off myself no matter where I am or what account I am using. The only problem is that recently AOL has started refusing my messages simply because they come froma NATed address. Bastards!!

    You also might want to add.

    define(`confDONT_BLAME_SENDMAIL', `GroupWritableDirPathSafe')

    Otherwise sendmail will break everytime you run Software Update. You can fix it by chmoding / 755. Alternatively you can add a "chmod 755 /" to the the end of your /etc/rc (since most updates seem to require a reboot anyway).

    Back in the day (OpenStep) Mail.app let you call sendmail as an app, but AFAIK it now needs to relay off an address. There may be a way around this but I don't know it.
    --
    It is cowardly, and a betrayal of whatever it means to be a Jew, to act as a white man

    -James Baldwin
  8. Re:Could some one explain. by good+soldier+svejk · · Score: 2, Informative
    I've always been confused by this. How does this gain anything? that is, presumbaly no matter where you are home, work on the road you have a ISP somewhere. and you send e-mail via them. If you dont have an ISP then how does send mail know where it can send its packets too and have them accepted?
    My ISP, Comcast, nee ATTbi, nee MediaOne, only allows relaying from their own addresses. I have the same policy on my sendmail servers at work ( I accept mail from external sources for internal routing, but not to relay to third parties). So if I am at work I can't relay off Comcast's servers and at home I can't relay off my own. By enabling sendmail in daemon mode on my loopback address (127.0.0.1, but not my public address) I can relay from anywhere no matter what email account I am using. The down side is that AOL has recently started refusing mail from Comcast's user IP range, so I can't e-mail my dad from home. Guess I'll need to move him to a better ISP.
    --
    It is cowardly, and a betrayal of whatever it means to be a Jew, to act as a white man

    -James Baldwin
  9. Re:Could some one explain. by bedouin · · Score: 2, Informative

    For one thing, if you run your own mail server you KNOW whether or not your message was delivered. Another thing is that it will be delivered instantly, not 2 or 3 minutes after it was sent, like with some ISP's mail servers.

  10. Re:is this all i need by bedouin · · Score: 4, Informative

    Well, you can make an alias from your UNIX mailbox, to Mail App's. Mail App uses normal UNIX boxes as far as I know.

  11. Use smtp.mac.com instead... by mactari · · Score: 3, Interesting

    I tend to agree with the assertion that you don't need sendmail on OS X; that's what Mail.app is for.

    The only time I've had a problem with my ISP's own smtp server, Mail.app automatically asked if I didn't want to use smtp.mac.com to send my mail. I don't have a .Mac account, so I was awfully impressed with OS X's desire to get my mail through, rain, sleet, hail, or whatever the bytes were doing today.

    That said, Commando-ing the command line is nearly always a good thing. Setting up a sendmail server is pretty neat for people who might not use Mail.app (wacky mutt users!) or are Darwin diehards -- or just command-line curious. Between Fink and apps like this, you can do what you used to have to be a BSD expert to achieve.

    But check Mail.app out again if you're using something else now. It's a much better app now than it was in OS X 10.0, when it was a pretty simple tech preview of the Address Book and spellcheck Cocoa textareas. And with Panther, the app seems to only be getting better.

    --

    It's all 0s and 1s. Or it's not.
  12. Ack! by General+Sherman · · Score: 3, Informative

    Please, all you people just starting up sendmail on your mac, please, OH PLEASE set it to only allow incoming connections from localhost or set it to have authorization required?

    Don't turn your mac into a spam relay.

    --
    - Sherman