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DNS And E-mail

Volume Number: 21 (2005)
Issue Number: 7
Column Tag: Programming

Mac In The Shell

DNS And E-mail

by Edward Marczak

Did You Know They're Related?

It is my charge to bring you all things Unix. To help you understand what's going on beneath the GUI. Sometimes, this involves troubleshooting. While DNS and e-mail no longer play exclusively in the Unix realm, they certainly spent their childhood there and have some Unixy-like scars to show for it. Not only did they grow up in the same era, they just happen to be first cousins. This particular column aims to be a tiny troubleshooting guide.

Family Tree

"DNS and e-mail?" I hear you ask. "They are such different systems, and do completely different things!" Ah! It's the differences allow them to complement each other, which is why they are such perfect mates. E-mail relies on DNS. In fact, most systems nowadays have some reliance on DNS. E-mail just won't get delivered without DNS. Kerberos not functioning? Check your DNS. Most other systems would just be cumbersome, as you'd have to specify other systems, not as a name, but as an IP address.

E-mail servers rely on DNS in several ways. Your outbound e-mail server must have access to DNS to lookup mail routing information. To receive e-mail, your Internet facing DNS servers must be set up correctly to let others know how to reach you. DNS mis-configuration is commonly a source of e-mail trouble.

DNS

Life without DNS cumbersome? Well, yeah - this is why DNS exists. Computers like numbers, people like names. The Domain Name System exists primarily to convert names, like www.apple.com, into an IP address (number), such as 17.112.152.32. It also helps us convert from number back to name. DNS has been pushed to do even more than these simple translations.

Bottom's Up!

I'm going to introduce these systems youngest first. Before DNS existed, the name to address translation took place by looking up entries in a flat-file called 'hosts'. This file still exists, and can still be used. There was a time when OS X ignored the hosts file, but it is now recognized by default. You can find it in /etc, where all good Unix boxes store the host file. When the Internet was small enough, current host files were copied between machines - actually, one master machine, via ftp.

Naturally, as the number of machines on the Internet grew, this system just didn't scale. In 1984, Paul Mockapetris released RFC 882 and 883 - the Domain Name System. Naturally, these RFCs were supplanted and augmented, but those two were the birth of DNS.

DNS provides a hierarchical, distributed database. Name servers are the programs responsible for transferring the database to clients (as appropriate) and to other servers. OS X ships with BIND (Berkeley Internet Name Daemon) as its name server. There are other servers, such as DJB DNS, MaraDNS, and even stand-alone DNS hardware such as Bluecat DNS. Tiger server, specifically, runs version 9.2.2 of BIND. While there are pros and cons to BIND, it is certainly the most popular name server on the Internet.

Enough history, on to the details! Please note that it is outside the scope of this article to dig into every facet of DNS, and I'll just be hitting on the basics (remember, we still have to get to e-mail!). If you administer a name server, need to know more about BIND or even walk by a machine running a name server, you owe it to yourself to pick up "DNS and BIND" by Albitz and Liu, published by O'Reilly. Best. DNS. Book. Ever. I still have my worn 2nd edition. The only reason I haven't picked it up in a bit is because I committed it to memory long ago.

The Details, Please!

Most techies (that's us) understand DNS structure. Generic top-level domains, such as 'com', 'mil', 'info' and 'org' hang just off of the root ("."). Delegated zones live beneath the gTLDs, and subdomains and hosts follow. When queried about a zone that it operates (or, is authorative for), the name server will consult its database. BIND uses a simple flat-file scheme for a database, that is read at name-server start up. Each entry in the database is referred to as a record. There are many different kinds of records, and I won't be covering them all, just the ones germane to this discussion.

The main record to understand immediately is the A, or "'address"' record. This provides the core functionality: it maps a name to an address. An excerpt from Apple's DNS may look something like this (the "'IN"' stands for "'INternet class"' - somewhat of a relic, but still a requirement):

www.apple.com.          IN A      17.112.152.32
mail-in3.apple.com.     IN A      17.254.13.8
nserver.apple.com.      IN A      17.254.0.50

So, when you request www.apple.com in your browser, your system asks DNS to resolve the name, and in turn is told '17.112.152.32'. (For those of you who know this cold, yes, this is a simplified version of how this all works). You can use DNS to help transition to a new server by changing the A record. Let's say you run web services at www.example.com. The A record for www points to 10.0.0.10. One day, you buy the biggest, shiniest new server. You could set it up as 10.0.0.11, configure it, and once ready, alter DNS to map www.example.com to 10.0.0.11. People don't have to learn a new name, buit they will get routed to the new server.

Didn't You Say Something About Mail?

Move all of that DNS information over in your brain for a moment; I'll tell you when to slide it back into the center again. E-mail has long been one of my favorite systems. I'm not sure why. It absolutely disturbs my inner core when an e-mail system is not working. I started off with sendmail (before the m4 macros were the way to write your cf files), and shifted to Postfix when it was still Secure Mailer. What is seemingly a very simple thing - moving a text file from point A to point B - actually has a fair amount of complexity.

If you've only ever configured the mail system via the GUI, or come from an Exchange, Kerio or Communigate background, there's a simple issue that you may not know about. The subsystem that is responsible for sending and receiving mail is completely separate from the subsystem that allows you access to your mail spool. When someone from the outside sends mail that is destined for your mail server, Postfix is responsible for receiving that mail via the SMTP protocol, figuring out what to do with it, and either delivering it personally, or handing it off to an intermediary. When you set up a mail client (or "MUA" - Mmail Uuser Aagent) to retrieve mail via the POP protocol ("boooooo!") or the IMAP protocol ("Yeah!"), Cyrus is handling those requests. When you send an e-mail via your MUA, be it Entourage, Mail.app, Eudora, whatever - once again, Postfix is responsible for talking to your mail client, queuing and sending the mail to the remote system. So how does this all tie together?

Once again, imagine you run all services for example.com. When mail destined for mail.example.com is presented to your OS X Server, Postfix, listening on port 25 for activity, springs into action. Postfix itself has several subsystems that deal with various stages of accepting, queuing and delivery. However, one of the first things Postfix must do, is decide whether or not this piece of mail belongs on this server or not! Is it really for 'example.com'? If so, is there a user by the name requested? Important questions, right? If the mail truly belongs here, it has to get added to the correct user's mail spool. In OS X's case, Postfix hands the mail off to Cyrus via LMTP.

Most people have heard of SMTP, the simple mail transfer protocol. This protocol is responsible for delivering mail between two systems over a network - typically over a WAN or the Internet. Somewhat lesser known is LMTP, the local mail transfer protocol. OS X uses LMTP exactly as designed: to allow two mail systems residing on the same machine to exchange mail (actually, these two can also be two separate machines on the same network). LMTP uses the same semantics as SMTP, but avoids queuing. LMTP must process each message as it isthey are received. It is also stipulated that LMTP must not run on port 25. In our case, LMTP exists as a socket in /var/imap/socket.

Once the message is handed off via LMTP, Cyrus is responsible for dropping the message in the proper user's mail store (specifically, Ccyrus' 'deliver' agent does this, although nowadays, 'deliver' is deprecated, and is just a wrapper for LMTP delivery). When a person commands their e-mail program to "'Get New Mail"' Cryrus is responsible for answering the request by accessing the mail store, and answering via the POP or IMAP protocols.

Uh-oh

You're a freelancer or in house IT person that's responsible for a mail system, and you get the call: "I'm not receiving any mail!" What to do? First, find out of it's just the person who called, or if the problem affects everyone. If you have an account on the system in question, send yourself a test message from your GMail account (unless, of course, someone from Google is reading this and you're trying to troubleshoot GMail. In that case, use Hotmail). If you receive it, great. It's likely limited to that one person that called.

If you didn't receive it, time to start looking at the logs. Let's stop right here for a second while I admit something. I love logs. I'm a bit obsessed with them. A future column will touch a bit more on logs, but let's just remind ourselves how important they are. Logs are the heart of your system. I typically keep one machine nearby that does nothing but watch logs for me. It's good to glance at so you get used to the rhythm. That way, when that rhythm gets broken, you can recognize it instantly. That said, you want to follow /var/log/mail.log right now. I recommend using 'tail -f' in terminal for this. Send that test message again. Is there an entry in the log for this?

OK, now's the time to dust off that DNS information. If there's no entry in the mail log, it's likely that the mail server is just fine, rather, it's DNS that is having an issue. As mentioned, there are several kinds of DNS records, the A record just being one. The MX record defines a 'mail exchanger' for the domain or subdomain. If that's not configured properly, mail isn't going to get delivered.

When I type up and send an e-mail, my MUA hands off the message to my e-mail server (or, Mail Delivery Transfer Agent - MTDA). The mail server then queues the message and figures out how to deliver said message. If my message is destined for steven@radiotope.com, the server must first find out where it is to send this mail. DNS has the answer. This is a three-part conversation that would go something like this:

example server: "Excuse me, DNS for radiotope.com, can you please give me your mail exchanger?"

radiotope DNS: "Sure, it's www.radiotope.com."

example server: "Oh. I've never dealt with that server before, what's its IP address?"

radiotope DNS: "No problem, that's 69.55.224.105"

example: "Thanks!"

example: "Pardon me, www.radiotope.com, I've got some mail for you!"

radiotope mail server: "I'll take that, thank you!"

Notice how much of that conversation happens with the DNS server. Fortunately, the mail server will cache the results for radiotope.com, and won't have to ask until the cache TTL (time to live runs out).

So, if DNS isn't correct, the mail will never hit the proper mail server, and you'll never see it in the log file.

I've had an incredible increase in the amount of mail server troubleshooting that I'm doing for people. Apple certainly hasn't had a perfect record here. Up until 10.3.4 in the Panther series, people were bitten with the 'log rolling bug'. That did get fixed. However, we're all still living with the 'reconstruct bug'. When you check the mail.log file, you may see entries like this:

Jul  5 10:33:38 mailserver deliver[379]: 
     connect(/var/imap/socket/lmtp) failed: Connection refused

Or, this:

Jul  3 04:49:27 mail postfix/pipe[8805]: 6E8AF9A9F2:
     to=<jimbob@example.com>, relay=cyrus, delay=135898, status=deferred 
     (temporary failure. Command output: couldn't connect to lmtpd: Connection refused_ 
     421 4.3.0 deliver: couldn't connect to lmtpd_ )

On a busy mail server, you'll see a lot of these. They're both commonly associated with a corrupt Cyrus database. Time to stop mail, and for a little explanation. Stop the mail services:

serveradmin stop mail

Although the issue here is with Cyrus, this command will stop both Postfix and Cyrus. You don't want things trying to deliver to a corrupt mail store. As mentioned earlier, Postfix hands the message to Cyrus via LMTP via a socket file. It was also mentioned that LMTP doesn't perform queuing - it is required to process each message as it's received. In this case, it can't. Either Cyrus isn't running at all, or it has corruption in its database. To see if Cyrus is running, look for the evidence of 'master' in your process list:

# ps ax | grep [m]aster
  206   ??  Ss     0:00.01 nfsd-master    
  227   ??  Ss     0:57.27 master
29133   ??  Ss     0:00.05 master

Whaaaa? There's two! For better or worse, both Cyrus and Postfix have their master processes named "master". You can see which is which with lsof:

lsof | grep master

You should see a group of master processes owned by root, followed by a group owned by cyrus (cyrus-imap on Tiger). If Cyrus is genuinely not running, watch your system log (/var/log/system.log) and hand crank it: "/usr/bin/cyrus/bin/master &". Naturally, you can also stop and start all mail services while watching the log.

Cyrus

Unlike many other IMAP and POP servers, Cyrus takes a different approach to handling mail. Traditional IMAP servers, such as UW-IMAP, really don't get involved in the delivery process at all. You tell them where the mail spool is, and they relay that to the user. In some cases, the IMAP server will be responsible for taking mail out of the system spool and moving it to a spool in the user's home. Not so with Cyrus. Once Postfix hands off the message to Cyrus, the 'deliver' agent is responsible for getting the mail into the correct mail queue.

Here's where Cyrus is completely different. Deliver will drop the message into the correct user's mail store, sitting at /var/spool/imap/user/(username) - this is the default location for OS X, and you can move it to another partition, so be aware if you have done so. "deliver" is Cyrus' Mail Delivery Agent (MDA). That's all standard, but Cyrus goes above and beyond this, keeping a database of mailboxes, ACLs (not the Apple filesystem ACLs: - Cyrus sports its own ACL list that can let others have access to your mailboxes. As far as I know, there is no Apple-official way to change the Cyrus ACLs), seen messages, quotas, etc. The databases that keep track of this are in BDB format, and live in /var/imap.

Like any database, there's always a chance that it will get corrupted or somehow out-of-sync. Sometimes, I've seen this happen with a system crash. OK, that makes sense. The disks went down dirty, and files didn't get closed. Oddly, I've also seen Cyrus go batty with no great explanation (however, I do sometimes show up on the scene to clean up, and let's face it, people aren't always 100% accurate about the events that lead up to the whole mail system going down). But if you're seeing errors in the logs like the two above, there's a good chance you have some Cyrus database problems.

Cyrus database problems can come in several flavors, so let's hit the highlights:

Permissions errors

Our good old friend 'permissions' is back! /var/imap should be owned by cyrus:mail, with perms of 755, all the ways down. Same goes for /var/spool/imap, with one exception: /var/spool/imap/user should be a little more restrictive: 700 for it and its contents.

If Cyrus can't read and write into those folders, it's going to have problems delivering and retrieving mail. So double-check those folders!

Damaged Socket File

You should really never see this condition. However, this is a variation on the first condition: the socket could have the wrong permissions assigned (although, that should never change unless you touch them!). Bonus: they auto create on Cyrus startup. Just nuke 'em from /var/imap/socket with mail services stopped. They'll get created properly when services are restarted. For the record, a Tiger server at minimum will look like this:

# ls -l /var/imap/socket
total 0
-rw-- -- -- -	1 cyrusima	mail 0 Jul 2 00:12 imap-1.lock
srwxrwxrwx	1 root			mail 0 Jul 2 22:50 lmtp

Database corruption

This seems to be the big one. There are several things that can go a bit batty here. I can't stress the importance of backups enough. The crummy thing is that to back up Cyrus properly, you need to shut down mail, and there's no great alternative on OS X. Hot backups here can lead to inconsistent states. Backup, backup, backup, and test, test, test! I mention this simply because restoring the database from the mail spool is really imperfect. There are certain things that can not be inferred from the mail store, so those things get set back to a default state.

Here's how this works: as Cyrus drops mail into the mail spool (/var/spool/imap) appropriately, it updates its databases (/var/imap). They're relatively independent - the mail spool can live without the database, however, that's where Cyrus stores all of the metadata (remember that stuff?), so it needs to be protected. Cyrus keeps watch over this by check-pointing the database at regular intervals. The tool that rebuilds the database is called 'reconstruct'. I'll spare you the long story and cut right to the chase: Apple's latest version of reconstruct is a bit FUBARed. The bad version snuck in under a 'security update'. There's an open source replacement that corrects the mistake that Apple's version makes. Get it here: http://www.sussex.ac.uk/Users/jamesg/reconstruct.zip. The (long) explanation for this takes place in this thread on Apple's support boards:

http://discussions.info.apple.com/webx?7@1022.JKM0abd8V6f.2@.68aec789/9

Is there any harm in running Apple's version? Well, yes. Apple's version will reset the internal time-stamp of messages to '0' (zero). This won't affect every mail client, but guess which two it will? Apple's Mail.app and Entourage - the two most popular mail client on OS X. How do you know if you've been hit with this? If, after a reconstruct, your mail clients are choking while trying to check for new mail, but webmail (using the built-in squirrelmail) is fine, sounds like this is the issue. Get the replacement from the URL above, choose the version appropriate for your platform (yes, this currently still exists in 10.4.1). Backup your original (mv /usr/bin/cyrus/bin/reconstruct /usr/bin/cyrus/bin/reconstruct.apple) and drop the replacement into the same directory (/usr/bin/cyrus/bin/reconstruct). Set the wheels in motion like this:

    1. Start a pot of water boiling. Now is no time to panic, and tea will do you some good. Preferably some green or camomile.

    2. Stop all mail services. If you didn't do so above, do so now: serveradmin stop mail

    3. backup /var/spool/imap and /var/imap...just in case

    4. Run reconstruct. You must do this as cyrus:

    sudo -u cyrus /usr/bin/cyrus/bin/reconstruct -i

    The '-i' flag here will rebuild sub folders for each user as well. You should see messages scrolling by as reconstruct works its way through each user. Depending on the size of the mail store, this could take some time. Now's the time to pour that cup of tea.

Once that is complete, try firing up the mail system again: serveradmin start mail. On rare occasions, this won't start Postfix. Sip that tea, and simply type: postfix start. No problem. At this point, mail should be flowing again. Queued mail, and new mail coming in should be getting delivered, and people should be able to access their mail. This alone will make them happy enough to ignore this issue: ALL of their mail will now be marked unread. Flags will be lost. But! Their mail will be back! Make the rounds, then finish off that tea. Maybe even get a cookie. What the heck.

Redundant Redundancy

A brilliant concept with DNS and mail is that you can specify multiple MX records. You can (and should) assign them a priority. "0" is the highest priority, with everything else being lower. So, when DNS specifies:

example.com.   IN   MX   10 ren.example.com.
example.com.   IN   MX   20 stimpy.example.com.

"10" is the higher priority server. That's where mail should go. However, if ren.example.com is down, the mail will get delivered to stimpy.example.com. For best effect, ren and stimpy should be on separate networks. In different buildings. In different states, if possible. If you run mail services in-house, see if your ISP will perform backup MX duties for you. Most will. Like backing up data nightly, having a backup mail server (or two...or three) is more than worth it. Don't walk this tightrope with no net: have a backup mail server with properly configured MX records.

In the previous section, we had to take our mail services out of commission while we repaired the Cyrus databases. If someone was trying to send us mail at that moment - something that has a very high probability - without a backup mail server, it's going to bounce back to them. We'll have dropped off the face of the Internet! However, with the backup server in place, the mail will get routed there, and be delivered to our main mail server once it's back on-line. Brilliant, just brilliant!

Other Troubleshooting

Naturally, for a mail server to receive mail, it must be accessible. I recommend that anyone who does network troubleshooting have an externally accessible machine - preferably through ssh, although ARD and Timbuktu will let you get a shell also. This will be used for the purpose of getting an outside view of the network you're currently working on.

To test SMTP, access your outside machine, get a shell, and type:

telnet mail.example.com 25

Of course, you need to substitute the Fully Qualified Domain Name (FQDN) of your mail server. You should receive a reply like this:

Trying 192.168.0.18...
Connected to mail.example.com.
Escape character is '^]'.
220 mail.example.com ESMTP Postfix

Type 'quit' and press return to get back to your prompt. If you do not get this greeting, either Postfix is not running, or something is blocking access. If your external test machine is on a residential network, it's likely that port 25 is blocked. Make sure you don't let that throw you off. You can have Postfix listen to both 25 and an alternate port by adding this line into /etc/postfix/master.cf:

8025     inet     n     -     n     -     smtpd

Where 8025 is the new port that Postfix will listen to. Save the file, and type:

postfix reload

to restart Postfix and allow it to incorporate this change.

You can test IMAP in a similar way. Again, using telnet, connect to port 143:

# telnet mail.example.com 143
Trying 192.168.0.18...
Connected to mail.example.com.
Escape character is '^]'.
* OK mail.example.com Cyrus IMAP4 v2.2.12-OS X 10.3 server ready

Just like the SMTP test, if you do not see this greeting, either Cyrus is not serving up IMAP for some reason, or the port is being blocked from you. While I haven't found an ISP that currently blocks IMAP, perhaps there is an errant firewall rule preventing access. When you're done here, type "01 logout" and press return.

Serendipity

Like this column, e-mail and DNS are completely intertwined. Both have nuances and pitfalls that require a bit of knowledge. I've been helping people out more and more frequently with mail issues. The sad news is that OS X's built in mail system is just about there, but not quite. The problems lie more on the Cyrus side - specifically due to the way they're implemented on OS X. You'll find plenty of stable Cyrus servers running on other platforms. Postfix, thankfully, is just a rock. When troubleshooting mail, remember: mail is really a bag of tricks, and not one single coherent system. There are, of course, other factors that will impact mail delivery, such as network design, choice of mail host, content filtering schemes, intermediary mail routers, firewall and/or NAT rules, and more. Many facets of your seemingly distinct pieces of network equipment are inherently intertwined.

This isn't always the easiest of stuff. Questions? Feel free to send 'em my way at emarczak@mactech.com.


Ed Marczak, owns and operates Radiotope, a technology consulting company that implements mail servers and mail automation. When not typing furiously, he spends time with his wife and two daughters. Get your mail on at http://www.radiotope.com

 

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The Intel Compute Stick, a new pocket-sized computer based on a quad-core Intel Atom processor running Windows 8.1 with Bing, is available now through Intel Authorized Dealers across much of the... Read more
Heal to Launch First One-Touch House Call Doc...
Santa Monica, California based Heal, a pioneer in on-demand personal health care services — will offer the first one-touch, on-demand house call doctor app for the Apple Watch. Heal’s Watch app,... Read more

Jobs Board

*Apple* iOS Specialist - TCML (United States...
AppleiOS Specialist Senior Apple /iOS Administrator/Engineer responsible for configuration and distribution of desktop, laptop and mobile devices to State Employees Read more
*Apple* Client Systems Solution Specialist -...
…drive revenue and profit in assigned sales segment and/or region specific to the Apple brand and product sets. This person will work directly with CDW Account Managers Read more
*Apple* Retail - Multiple Positions (US) - A...
Sales Specialist - Retail Customer Service and Sales Transform Apple Store visitors into loyal Apple customers. When customers enter the store, you're also the Read more
*Apple* Support Technician IV - Jack Henry a...
Job Description Jack Henry & Associates is seeking an Apple Support Technician. This position while acting independently, ensures the proper day-to-day control of Read more
*Apple* Client Systems Solution Specialist -...
…drive revenue and profit in assigned sales segment and/or region specific to the Apple brand and product sets. This person will work directly with CDW Account Managers Read more
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