Question

Mac OSX Sending illegal SMTP data

Asked by: tlpadmin

Greetings,

I have an issue regarding a Macintosh running OS X sending tremendous amounts of SMTP email.
This issue is believed to be viral. (Please read this entire post before you comment on this statement.)

Facts:
I come in to work to find our Exchange servers being blacklisted by CBL, SpamCop, Ironport, etc.
After inspection I find that a computer within my network is sending SMTP traffic
I begin sniffing packets and investigation and all fingers point to a statically-assigned iMac.)
This mac has been on the network for an extended period of time.
This mac was here before I ever started, so I cannot say for certain what all configuration has been done.
According to the cbl, "This is the Cutwail BOT"
Every bit of research I do on Cutwail bot states very clearly this infects PCs, not MAC.
This mac does not run Windows at all. Not in paralelles, bootcamp, crossover or any of the other methods out there.

I am concerned that someone somewhere has malformed Cutwail and devised a method to get it running on Mac OSX without WINE or other emulation.
This speculation again comes from the fact that this mac has been running happily on this network for over a year now, and is just now getting this problem.

The operator of this machine stated he has not installed any new software recently. Nor has this machine had any noteworthy changes made to it.

In the PC side of business you could say I've got more than my fair share of experiences.
However in the Mac world, I rate nothing more than a pup.
I know this OS runs a variant of 'nix, but without a shell to start checking things, I'm aptly helpless.

What steps can I take to troubleshoot this? What methods or tools exist that I am simply ignorant to? What is the IT standard for diagnosing Macs?

I've googled myself blue in the face and keep coming up with answers that aren't really helpful.

I have found a fair amount of tools, but as a support technician I certainly don't want to buy software that very likely will do me no good.

(on a side note, I did contact Apple for support, and they were far from helpful. They referred me to something called "truecrypt" stating that it was used for this sort of issue... It's not even closely related to this issue.)

This Question has been solved and asker verified All Experts Exchange premium technology solutions are available to subscription members.

Subscribe now for full access to Experts Exchange and get

Instant Access to this Solution

  • Plus...
  • 30 Day FREE access, no risk, no obligation
  • Collaborate with the world's top tech experts
  • Unlimited access to our exclusive solution database
  • Never be left without tech help again

Subscribe Now

Asked On
2008-08-19 at 13:56:07ID23661178
Tags

Apple

,

Mac OS

,

X

,

SMTP services

Topics

Mac OS 10.5 (Leopard)

,

Apple Operating Systems

,

Mac OS X

Participating Experts
2
Points
500
Comments
18

Trusted by hundreds of thousands everyday for fast, accurate and reliable tech support.

  • "The time we save is the biggest benefit of Experts Exchange to Warner Bros. What could take multiple guys 2 hours or more each to find is accessed in around 15 minutes on Experts Exchange." Mike Kapnisakis, Warner Bros.
  • "Our team likes having a resource that is more secure than just using Google and most experts using this service really know their stuff. It's nice to look here first versus using Google." Dayna Sellner, Lockheed Martin
  • "Anytime that I've been stumped with a problem, 9 out of 10 times Experts Exchange has either the accepted solution or an open discussion of the potential solution to the problem." Kenny Red, eBay Inc.

See what Experts Exchange can do for you.

Got a question?

We've got the answer.

Experts Exchange has been collecting answers to technology questions since 1996…3 million and counting! If you have a question, chances are we already have your answer.

Screenshot of Experts Exchange Knowledgebase

Need individual assistance?

Our experts are ready to help.

If you can't find the exact answer you're looking for, ask our exclusive community of 50,000 experts. You’ll get a personalized answer from a trusted professional.

Screenshot of Experts Exchange Knowledgebase

Want to learn from the best?

Read articles from industry experts.

Thousands of free tech tips, tricks, how-to’s and tutorials are available in our peer reviewed articles section. See for yourself how smart our experts are, no login required.

Screenshot of an Article

Working on a long term project?

Store your work and research.

Save solutions to your questions, answers you’ve discovered through searching plus helpful articles in your personal knowledgebase for easy future access.

Screenshot of Experts Exchange Knowledgebase

Access the answers to your technology questions today.

Subscribe Now

30-day free trial. Register in 60 seconds.

What Makes Experts Exchange Unique?

Members of the expert community talk about why the experience at Experts Exchange is different than what you will find anywhere else.

Trusted by the world's most respected brands.

image of each brand's logo

Faithfully serving IT professionals since 1996.

Experts Exchange Logo

Try it out and discover for yourself.

Subscribe Now

30-day free trial. Register in 60 seconds.

Related Solutions

  1. how do i burn a mp3 disk on my pc then read it on my iMac …
    how do i burn a cd of mp3s on my pc then read it on my iMac with OSX 10.2.3. I am attempting to copy my mp3 collection off my PC laptop and load it on my iMac to sync with iTunes. I prefer the iTunes interface over my PC interface to the iPod.
  2. OSX and OS9 network
    Hi, I have three macs running OSX 10.2.6 and one imac running OS9.2. The three OSX machines are networked together through an ethernet hub, and run fine, but i cannot get the OS9 machine onto the network. It does not see any other machines, and is not recognised by the other...
  3. OSX install
    Yesterday I was able to salvage a PowerPC G3. not having a great deal of exposure to Mac OS's it was perfect for a reference machine. Currently it's running OS 9.2, it has a G3 266Mhz cpu, 352Mbs of RAM and a 4GB hard drive. I'd like to install OSX on this machine but wh...

Free Tech Articles

  1. WARNING: 5 Reasons why you should NEVER fix a computer for free.
    It is in our nature to love the puzzle. We are obsessed. The lot of us. We love puzzles. We love the challenge. We thrive on finding the answer. We hate disarray. It bothers us deep in our soul. W...
  2. SCCM OSD Basic troubleshooting
    SCCM 2007 OSD is a fantastic way to deploy operating systems, however, like most things SCCM issues can sometimes be difficult to resolve due to the sheer volume of logs to sift through and the dispe...
  3. Migrate Small Business Server 2003 to Exchange 2010 and Windows 2008 R2
    This guide is intended to provide step by step instructions on how to migrate from Small Business Server 2003 to Windows 2008 R2 with Exchange 2010. For this migration to work you will need the fo...
  4. Create a Win7 Gadget
    This article shows you how to create a simple "Gadget" -- a sort of mini-application supported by Windows 7 and Vista. Gadgets can be dropped anywhere on the desktop to provide instant information, ...
  5. Outlook continually prompting for username and password
    There have been a lot of questions recently regarding Outlook prompting for a username and password whilst using Exchange 2007. There are a few reasons why this would happen and I will try to cover t...
  6. Backup Exchange 2010 Information Store using Windows Backup
    There seems to be quite a lot of confusion around the ability to backup Exchange 2010 using the built in Windows Backup feature. This stems from the omission of this feature prior to Exchange 2007 s...

Cloud Class Webinars

  1. Avoiding Bugs in Microsoft Access
    Alison Balter takes and in-depth look at avoiding bugs in Access. In this webinar you will learn about using the immediate window to debug your applications, invoking the debugger, using breakpoints to troubleshoot, stepping through code, setting the next statement to execute, ...
  2. Top 10 Best New Features in Visio 2010
    Scott Helmers gives live demonstrations of the top 10 new features in Visio 2010. This webinar will teach you how to create compelling diagrams by adding shapes to the page with a single click, linking the shapes in a diagram to data in Excel (or SQL Server, or SharePoint), ...
  3. IT Consultant Business Secrets Revealed
    Michael Munger, Experts Exchange tech pro and IT consultant, pulls back the curtain on his very successful businesses and answers question on every IT consultant and business owner should know about. He shares secrets on what he did to solve the 5 most common problems in IT, ...
  4. Disaster Recovery and Business Continuity
    Quest CTO, Mike Billon, gives an overview of the steps involved in building a dunamic disaster recovery plan. Through case studies and an examination of software/hardware tooles for monitoring and testing, you'll gain a better understandin of where you are, where you want ...
  5. Organize Your Visio Diagrams with Containers and Lists
    Scott Helmers uses cross functional flowcharts, wireframe diagrams, data graphic legends and seating charts to teach you: how to ustilize all three new structured diagram components in Visio 2010, the best practices for organizeing shapes in previous version of Visio, how to organize ...
  6. How to Us Objects, Properties, Events and Methods in Microsoft Access
    Alison Dalter gives an in-depbth look at objects, properties, events and methods in Microsoft Access. In this webinar you will learn about using the object browser, referring to objects, working with properties and methods, working with object variables, understanding the ...

Join the Community

Give a Little. Get a Lot.

Join the community of experts here and help other tech pros by answering question in your area of expertise. You can earn FREE access to all Experts Exchange's premium features and resources.

Join the Community

Answers

 

by: strungPosted on 2008-08-19 at 15:31:16ID: 22264513

I have a hard time believing it is the Mac. Try shutting down the Mac and see if the problem disappears.

 

by: tlpadminPosted on 2008-08-19 at 15:42:43ID: 22264589

In a discussion with the user of this mac, they informed me that the former IT guy could not get the user into email properly. He stated that he was able to get email to send, but could not receive. Things were beginning to make more sense.

Quick research resulted in a partially helpful website at http://technosailor.com/2006/10/25/how-to-configure-your-mac-to-send-mail-regardless-of-where-you-are/ which offered instruction on how to set up your Mac to act as an SMTP server. A tool called Postfix.

I finally found the shell in Mac OSX. Aparently it's called "Terminal" and was found in Applications > Utilities.

From there some of my old Linux training came back to me and I was able to traverse the directory structures and run vi to edit files. I was able to browse the postfix configuration files found in/etc/hostconfig.

Now the problem is clear to me. It's not a virus, but a foolish admin who set up postfix rather than just configuring email to access the exchange server. (Right. Doesn't make sense to me either.) Postfix, being the good application it was, was happily routing emails for unauthenticated connections. A botnet managed to find this machine, and began to happily spam away. The statements above about there being a malformed virus have resulted as nothing more than a false-positive.

To stop postfix from running, I ran "sudo /bin/launchctl unload -w /System/Library/LaunchDaemons/org.postfix.master.plist" (minus the quotes, of course.) Though I understood this, the main clue came from http://osx.topicdesk.com/content/view/69/45/

It's worth mentioning that this system was not running cyrus, so I did not have to run the second command.

No points awarded, as I've figured this out. Hopefully the post may aid others in similar situations when/if they arise.

 

by: tlpadminPosted on 2008-08-19 at 15:43:25ID: 22264593

Yes, indeed this was a mac. Upon disconnecting the mac from the network, the traffic stopped. However this is explained in my notes above.

 

by: strungPosted on 2008-08-19 at 17:17:59ID: 22265127

 

by: tlpadminPosted on 2008-08-20 at 09:35:20ID: 22271485

Thanks strung, but I don't know how that search holds relevance to my questions.

What steps can I take to troubleshoot this?
What methods or tools exist that I am simply ignorant to
What is the IT standard for diagnosing Macs?

I wasn't asking how to fix postfix or cyrix. I did not have any certificate troubles with configuring entourage, as we have signed certificates from a well-known root ca. I think the former admin just did not know how to set up mail on a mac.

(tongue in cheek I was told later by a director that the former admin was deathly afraid of macs. Go figure.)

Again, anyone in my position that was ignorant to supporting mac os x, the answer was Terminal. Terminal opens the Unix shell to which you can use 'common' unix commands. (if you weren't aware, Mac OSX is based on a breed of Unix commonly called Darwin Unix.)

if you don't know any unix and need help, you're in luck. There's a stong online community and plenty of help pages out there. I might suggest starting at the source. http://manuals.info.apple.com/en_US/Command_Line_Admin_v10.5.pdf is a command line manual for using Mac OS X 10.5. They direct this at OS X Server, however don't let that cause you to loose focus. OS X 10.5 server and 10.5 workstation are all built on the same basic technology, and so the greater majority of the commands cited in this manual will work on Leopard.



Other sites that may be helpful:

A brief note about getting help on commands: http://docs.info.apple.com/article.html?path=Mac/10.5/en/8791.html

Common Commands used for troubleshooting unix: http://publib.boulder.ibm.com/infocenter/db2luw/v8/index.jsp?topic=/com.ibm.db2.udb.doc/admin/r0008948.htm

Tips for troubleshooting Unix: http://www.december.com/unix/tutor/trouble.html

 

by: strungPosted on 2008-08-20 at 09:41:08ID: 22271563

Sorry, that response was posted to the wrong thread.

To answer your questions, the Activity Monitor App (found in \applications\utilities ) and a third party shareware app called Little Snitch http://www.obdev.at/products/littlesnitch/index.html would probably have tracked this problem down.

Sorry, I didn't recommend those at the time. As there are no Mac viruses, my knee-jerk reaction was that it was not likely the Mac causing the problem. It never occurred to me that someone might have installed an SMTP server on it.

 

by: tlpadminPosted on 2008-08-20 at 14:07:26ID: 22273939

Strung,

I am a big proponent for credit-when-due; I'm also a big proponent of industry standards.
Sadly, the industry standard for mac  support seems to widely be accepted as "Call apple for support." as I discovered while talking to a few self-proclaimed mac experts.

Right.

I've since familiarized myself better with the utilities that are here for my use. The activity monitor was surprisingly informative. I honestly expected less from the application.

For that direction, I'm prepared to change my closure request and issue half points... however I would like to bait you into this a bit more to award you full credit.

Are there any other Industry Standard tools you can think of that may in the future assist me in working on Mac OS X?

By industry standard, I refer to something established by authority, custom, or general consent as a model or example. Your historical experience in this environment will certainly speak volumes to me over the 'call apple' standards I've been suggested recently.

Regards,
-TLP Admin

 

by: strungPosted on 2008-08-20 at 15:50:48ID: 22274654

OS X comes with a wealth of tools. Just hunt through the \applications\utilities folder.

Console.app allows you to read the very extensive logs kept by OS X.  

Disk Utility is a good disk repair utility as well as a utility to create disk images.  

Network Utility is worth a good look at.

Keychain Access allows you to review an manipulate stored passwords and certificates.

As well there are a lot of freeware and shareware tools. See:

http://www.macfixit.com/staticpages/index.php?page=20021011090449544 for a pretty comprehensive list (not sure if you have to be a member to access that page, but if you plan on supporting Macs, you should take out a membership. Go to the home page: http://www.macfixit.com ).

See also http://www.macorchard.com (for Mac internet software) and http://wwwversiontracker.com (for lists and reviews of new software.) and http://www.apple.com/downloads/

Pacifist ( http://www.charlessoft.com/ ) is the Mac equivalent of the Windows CabViewer.

CarbonCopyCloner ( http://www.bombich.com) and SuperDuper ( http://www.shirt-pocket.com/SuperDuper/SuperDuperDescription.html ) are shareware equivalents of Norton Ghost. http://www.bombich.com also has network deployment software to let you deploy cloned drives over a network.

One utility you should install on every Mac you have is SMARTReporter:  http://www.corecode.at/smartreporter/index.html  Smartreporter puts a green icon on your menubar. It then runs an hourly S.M.A.R.T. disk check and if it detects an imminent hardware failure, the green icon turns red. It can be set not to run disk check if you have a laptop running on batteries.

If you are running OS X 10.5.x, familiarize yourself with the built-in Time Machine software ( http://www.apple.com/findouthow/mac/#tutorial=leopardtimemachine ) which brings the power of shadow copies to the Mac desktop without the need of server software.

There are a number of standard commercial utiities:

DiskWarrior ( http://www.alsoft.com ) is a heavy duty commercial disk repair utility that will repair drives that Disk Utility can't. TechToolPro ( http://www.micromat.com ) is similar but adds pretty comprehensive hardware diagnostic tests. (By the way, all Macs ship with a hardware diagnostic CD).

DataRescue II will recover data from drives that are so badly damaged that neither Disk Warrior nor TechTool can repair them, even if the drive is so badly damaged that it won't mount. It will also recover accidently erased files (as long as they were not secure deleted :  http://www.delamainit.com/articles_how-tos/apple-mac-osx/secure-erase-hard-drive.html ).

Although not utilities, you should download and install the following free software on your Macs:

Firefox:  http://www.mozilla.com/en-US/firefox/

Flip4mac: http://www.microsoft.com/windows/windowsmedia/player/wmcomponents.mspx (Allows the Mac to play .wmv files in Quicktime).

Perian: http://perian.org/ (allows the Mac to play Flash and other codecs).

VLC: http://www.videolan.org/vlc/ general purpose media player

I will probably think of some more and if I do, will add another post.





 

by: strungPosted on 2008-08-20 at 16:04:00ID: 22274729

Forgot Stuffit Expander:  http://www.stuffit-expander.com/stuffit-expander.html?mv1=aUS031&gclid=CMf7n5vCnZUCFQEGQQodETVSjQ which will expand just about any archive file known to man and is free.

Onyx:   http://www.titanium.free.fr/pgs/english.html  is a multipurpose tool to clean caches and run maintenance scripts.

The free Windows Remote Desktop for Mac:  http://www.microsoft.com/mac/products/remote-desktop/default.mspx allows Macs to control WinXP Pro computers remotely.

 

by: strungPosted on 2008-08-20 at 16:14:32ID: 22274799

Disk Utility will also partition drive, by the way and repair access permissions.

 

by: strungPosted on 2008-08-20 at 16:23:46ID: 22274840

Little known trick. On your Mac go to:  http://localhost:631/printers/

 

by: strungPosted on 2008-08-20 at 16:25:30ID: 22274848

Neo Office - free Open Source competitor for MS Office, will even open old WordPerfect files and convert them to MS Word format.

http://www.neooffice.org/neojava/en/index.php

 

by: strungPosted on 2008-08-20 at 16:26:01ID: 22274852

Sorry you asked?  :)

 

by: strungPosted on 2008-08-21 at 06:30:06ID: 22279268

One more thing, (as Steve Jobs is famous for saying)... One of the most useful Mac repair tools for which I don't think there is a Windows equivalent is Target Disk Mode. If you have a Mac that won't boot, you can connect it to a second Mac using a Firewire cable. Booting the broken Mac while holding down the T key will boot it into Target Disk Mode which will cause its hard drive to mount as an extra volume on the good Mac. You can then run all your diagnostics from the good Mac, recover files, re-initialize the hard drive, or do whatever else you want.

 

by: tlpadminPosted on 2008-08-21 at 08:32:41ID: 31488191

What can I say? You've a grand library of tribal mac knowledge; even if you don't consider it as such. Best regards and +respect. Thanks a lot for your guidance.

 

by: tlpadminPosted on 2008-08-21 at 08:46:21ID: 22280805

Strung,

Sorry? Nonsense! I never regret learning, even if it's a painful process ;D

Some of these tools are really cool... its a shame I don't have a mac at my disposal. The more I tinker with these, the more I like them. (which says a lot from an old Windows/Linux admin. We tend to get stuck in our old habits.)

Points awarded as they've been well-earned. This will certainly aid me in future troubleshooting and working with the small handful of macs we have here.

 

by: ehannerPosted on 2008-10-31 at 03:07:45ID: 22848659

Wow Strung, what a resourse! Thanks!!!

20120131-EE-VQP-002

3 Ways to Join

30-Day Free Trial

The Experts

98% positive feedback on 31,087 answers since March 2000. angeliii is a Microsoft Most Valuable Professional for his work with MS SQL Server & Develoment.

He has also proven his knowledge of Visual Basic Programming, PHP Scripting and Oracle Databases.

The Experts

97% positive feedback on 10,752 answers since July 2000. lrmoore has more than 18 years experience in the networking industry.

The six-time Mircosoft MVPs specialties include firewalls, virtual private networking, and network management.

Testimonials

"...and excellent source for support... Kind of like having your very own IT dept." Electriciansnet

Testimonials

"I was apprehensive at signing up at first. However... it has already made my life as an IT administrator much easier." JaCrews

Testimonials

"WOW! You guys have great, active, and knowledgeable people on here." moore50

Business Clients

Business Clients

In the Press

"If you’ve got a question... Experts Exchange can supply an answer.”

In the Press

"...an invaluable aid for both IT professionals and those who require tech support."

In the Press

"where IT professionals provide quick answers on just about any topic"

Business Account Plans

Loading Advertisement...