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Why do I want Greylisting? Why does the UTM Greylist everything not rejected?

I am fully aware of what Greylisting is, but I am asking myself why would I want to use it and MOST IMPORTANTLY does the Sophos UTM SMTP Proxy use it by default or is it due to something I failed to setup correctly on the UTM or even another problem like Sender Verification failing and triggering Greylisting as a slow alternate method of sender verification??? While a great idea in principle, it caused at least a 7 minute delay in delivery to valid recipients and is not something I think I should have to live with as a default action.

I can bypass Greylisting by unchecking it in the profile since I am using profiles for more granularity. As an alternative, I can add all valid recipients to an exception rule Skipping: Greylisting FOR these recipient addresses. Can someone suggest a better way?

My question is: Is Greylisting everything a default action for all mail handled by the SMTP proxy or is there something that needs to be configured in the UTM to keep it from happening?

Finally, what is the consequence of disabling it?

Any help appreciated.


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  • Just my opinion...[[:)]]

    You observed 7 minute delay, UTM built-in help says 5 minutes, and my experience from the field is up to 15 minutes.

    I personally don't use it, it confuses end-users and brings a lot more support calls from the clients to me. 
    Not to mention mail deadlines (for example adds to be printed in tomorrow edition of newspapers or tender documentation that officialy must be delivered by e-mail before exact time).

    I worked in the past with many AS/AV solutions for Exchange server, and was first introduced to greylisting feature when I was starting with Sophos UTM product. Even Sophos PureMessage for Exchange doesn't have it (unless in some recent release). 

    Even without that feature all of my e-mail server implementations lived happy without (many) spams for years...[[:)]]
  • Greylisting is a great way to reduce spam -- it only delays an email delivery for 5 to 15 minutes (depending on the sending system's email config; typically 5 minutes or so) for the INITIAL email sent from a new IP to the proxy... no real complaints from any of my customers regarding having this enabled.

    CTO, Convergent Information Security Solutions, LLC

    https://www.convergesecurity.com

    Sophos Platinum Partner

    --------------------------------------

    Advice given as posted on this forum does not construe a support relationship or other relationship with Convergent Information Security Solutions, LLC or its subsidiaries.  Use the advice given at your own risk.

  • Greylisting is a great way to reduce spam -- ...


    Bruce, 

    It would be very interesting for me to see how is Greylisting rated in "Top Blocked Spam Reason" percentage statistic in a production environment (from any of your customer UTM implementations) . 

    Maybe I will be convinced to change my mind and approach regarding this feature.
  • If I where to keep Greylisting enabled, would there be some kind of Whitelisting of senders that have previously sent an email that was successfully delivered after Greylisting?

    Or does every sender get Greylisted every time?

    If there is such a Whitelisting, how long does the sender stay whitelisted? i.e. is there a TTL after which a sender must go through Greylisting again?

    Best Regards - HTG
    Frustrated Sophos Partner seeing all the things
    that brought me to Sophos slowly slip away.
    RIP astaro.org

  • Bruce, same question as vilic - when's the last time you ran a test (I realize that there's no statistic kept concerning the number of greylisted emails that weren't resent).

    I think the greylisting triad is sender/sending-IP/recipient.  After a successful delivery, the result is kept in what you have called a whitelist for a week (I think) after the last successful delivery.

    I haven't had anyone using greylisting for years since I saw no change in blocking percentages after de-selecting it experimentally in two sites.  Maybe I didn't do a good enough test and Bruce will explain.

    Cheers - Bob
     
    Sophos UTM Community Moderator
    Sophos Certified Architect - UTM
    Sophos Certified Engineer - XG
    Gold Solution Partner since 2005
    MediaSoft, Inc. USA
  • Nothing to explain, really...  I'm not saying we're catching a LOT of spam with Greylisting, but several a day (especially ones carrying 0-day payloads) is enough for me to enable it.  I don't see a negative (a real one) with having it enabled.  To each his own.

    CTO, Convergent Information Security Solutions, LLC

    https://www.convergesecurity.com

    Sophos Platinum Partner

    --------------------------------------

    Advice given as posted on this forum does not construe a support relationship or other relationship with Convergent Information Security Solutions, LLC or its subsidiaries.  Use the advice given at your own risk.

  • After a successful delivery, the result is kept in what you have called a whitelist for a week (I think) after the last successful delivery.

    Bob, I spoke with someone at Astaro / Sophos a few years ago, and they said then that Greylisting's retained memory of previous senders had been enhanced to a year. And though I haven't specifically tested, in my experience, I believe that to be correct.

    The only time I hear from a client about delays that I can pin on Greylisting, it's always about the initial receipt of emails from a new sender.  So, in other words, not very frequent at all.

    Incidentally, wouldn't the corollary of a Greylist "whitelist" would be to add the sender to an exception list?
  • ...Greylisting's retained memory of previous senders had been enhanced to a year...

    From the exim.conf file
    Maintainer: Micha Lenk 
    
    Maybe Micha can clue us in[[:D]]

    GREYLIST_RETRY_HOST_CLEANUP = ${lookup pgsql{DELETE FROM greylist_retry_hosts \
                                  WHERE (($tod_epoch - stamp) > (60*60*24*30))}{1}{1}}
    seems like its 30 days

    I haven't used greylisting since way back when we were still using spamassassin as our spam engine[[:D]] I mostly rely on country blocking now but that can be difficult to implement in certain environments.
  • Bruce, a new thread in the German Forum got me to thinking about this conversation over four years ago, so I did some more research and testing.  They all speak English and it's easier for me to respond in English.  I posted the following there:

    I haven't recommend greylisting for years, but others whom I respect do, so I'm experimenting with it again.  I saw a 2018 study where roughly 2/3 of greylisted emails were finally delivered, with 1/3 not retried - one assumes those were from spammers.  One of my clients that uses greylisting saw only 56% retried successfully so far in June.

    I had thought that the SMTP Proxy used only the triad of sending IP, sender and recipient, but I realize now that it also uses the subject.  This means that greylisting occurs after DATA, so that's after rejections for RBL, rDNS/HELO, local Blacklists, Recipient verification and SPF.  I also see ctasd reports 'unknown' in the line above the greylisted message, so we know that the temporary rejection occurs after the anti-spam tests that would result in rejection have been passed.  The advantage is that malware scans, which are expensive, are skipped unless the message is resent and accepted.

    There are situations where Exceptions for greylisting should be made such as addresses to which orders are sent where there's a cut-off time.  Also, mailing services like Constant Contact will use a different IP virtually every time a greylisted email is resent. 

    I would appreciate your comments/corrections here or on the German thread.

    Cheers - Bob

     
    Sophos UTM Community Moderator
    Sophos Certified Architect - UTM
    Sophos Certified Engineer - XG
    Gold Solution Partner since 2005
    MediaSoft, Inc. USA
  • On implementation:   

    You have identified the control methods.  You can turn it on or off globally or by target domain.  You can also turn it off with an exception.   In this respect, UTM will do whatever you want it to do.

     

    On the complications:

    The world's legitimate mail is coming from fewer and fewer sources:  Gmail, Outlook.com, Proofpoint, Mimecast, Cisco, etc.    These organizations are so large that you cannot keep track of the IP addresses that they are using, and it is possible that the IP address will change on every delivery attempt.    Users in this forum complained that they were seeing 24-hour delays from Outlook.com with graylisting enabled.   Other posts have indicated that Sophos maintains an internal exception list for these big organizations, and that they updated their list to correct the Outlook.com problem.   The best solution would be to have exceptions defined using SPF syntax, so you can say "bypass graylisting for anything coming from Outlook.com servers".   (Not because they are immune from bad behavior by their clients, but they are not going to be scared away by graylisting so it is useless as a defense for messages coming from them.)

    On my UTM configuration, I have never tried to use it.   On another environment with weak spam filtering, I have turned off graylisting and seen no significant change in spam levels.  So I am a skeptic.

     

    On data analysis:

    The SMTP logs are rather difficult to parse into coherent data.   I have just completed a redesign of my log parsing tools while chasing the antispam check failure errors that are mentioned in a new post that I started this morning.  It should be possible to collect data about messages that are not retried when graylisting is off, but it will require significant effort.   Someone can send me a PM if you want my code (which uses a SQL database).