Hi Simon,

> >Can we achieve the first 2 items of this measurement by doing a TCP 
> >traceroute on port 25?
> I would say no. Using TCP Traceroute, you can may check for 
> reachability/responsiveness of the host, but not the actual service (smtp).

That would would indeed mean a combination of TCP and SSL measurement to 
achieve all 3 required functions. Is it problematic if the result comes from 
multiple steps? If so, can you explain how?

I just noticed that the SSL measurement offers a time to connect, response 
time, certificates as well as SSL alerts which may be leveraged, see here: 
https://atlas.ripe.net/docs/apis/result-format/#version-4610 
<https://atlas.ripe.net/docs/apis/result-format/#version-4610>, under "Version 
4610 TLS (SSL) GET Cert”. TCP traceroute may not be necessary in this case, 
although I understand it is typically used to determine service availability.

> >Does the SSL measurement cover the intended use cases?
> I would say no. Correct me if am am wrong. Usually (for example HTTPS or 
> LDAPS) the SSL/TLS encryption starts right after the TCP 3-way Handshake was 
> successfull. For SMTP, that doesn't work. That's because regular SMTP 
> communication starts first, so both sides can negotiate if SSL/TLS encryption 
> is possible (via Enhanced SMTP Status Codes). However, as far as i know, 
> OpenSSL does support SMTP and STARTTLS. So you could probably modify the 
> existing SSL measurement.
> 
> Keep in mind that there's also MTA-STS and DANE, which are really enhancing 
> SMTPs security. A dedicated SMTP measurement would be a good thing.


You’re correct, the current SSL measurement does not support any form of 
STARTTLS, this is something that would have to be considered for 
implementation. I assume, much like with SMTP, similar cases could be made for 
IMAP4/POP3 or XMPP.
I would like to understand if there are particulars you are looking for that 
need to be considered outside of STARTTLS support?

Regards,

Michel


> On 23 Sep 2022, at 17:08, ripe....@toppas.net wrote:
> 
> Hi Michel,
> 
> >Are we monitoring the Internet or monitoring a service using the proposed 
> >SMTP measurement?
> First of all, we are monitoring the service of a specific target. Same as 
> http or ntp measurements, just another protocol. But we also monitor the 
> Internet. Using an SMTP measurement, we could identify censorship or discover 
> Man-in-the-middle attacks (downgrade attack by suppressing the STARTTLS 
> command).
> 
> >Can we achieve the first 2 items of this measurement by doing a TCP 
> >traceroute on port 25?
> I would say no. Using TCP Traceroute, you can may check for 
> reachability/responsiveness of the host, but not the actual service (smtp).
> 
> >Does the SSL measurement cover the intended use cases?
> I would say no. Correct me if am am wrong. Usually (for example HTTPS or 
> LDAPS) the SSL/TLS encryption starts right after the TCP 3-way Handshake was 
> successfull. For SMTP, that doesn't work. That's because regular SMTP 
> communication starts first, so both sides can negotiate if SSL/TLS encryption 
> is possible (via Enhanced SMTP Status Codes). However, as far as i know, 
> OpenSSL does support SMTP and STARTTLS. So you could probably modify the 
> existing SSL measurement.
> 
> Keep in mind that there's also MTA-STS and DANE, which are really enhancing 
> SMTPs security. A dedicated SMTP measurement would be a good thing.
> 
> BR,
> Simon
> 
> 
> 
> On 23.09.22 16:04, Michel Stam wrote:
>> Hi everyone,
>> 
>> Great that this request sparked a good discussion on the merits of a 
>> measurement, as well as its potential impact on servers around the world. 
>> Good to see this!
>> 
>> So I’m going to do a quick recap here, hoping that I capture the intent and 
>> the concerns correctly. Please correct me if I err.
>> 
>> The intent of the measurement would be to validate whether an SMTP server is:
>> reachable
>> responsive
>> capable of secured transmissions
>> 
>> The concern is that such a check would trigger one of a variety of anti spam 
>> measures in place around the world, and/or cause undue traffic to SMTP 
>> server operators.
>> 
>> With this in mind, I am wondering: 
>> Are we monitoring the Internet or monitoring a service using the proposed 
>> SMTP measurement? 
>> Can we achieve the first 2 items of this measurement by doing a TCP 
>> traceroute on port 25?
>> Does the SSL measurement cover the intended use cases?
>>  Is it worth exploring STARTTLS support as an extension and what would the 
>> implications be?
>> 
>> Have a good weekend!
>> 
>> Best regards,
>> 
>> Michel
>> 
>>> On 21 Sep 2022, at 00:11, Avamander <avaman...@gmail.com 
>>> <mailto:avaman...@gmail.com>> wrote:
>>> 
>>> > Making arguments based upon extreme cases, assumptions, or 
>>> > potential-for-collateral-damage is not scientific. "I know one that even 
>>> > [...]" Anecdotal  evidence isn't scientific.
>>> 
>>> From the perspective of your previous sentences that's kinda humorous. "To 
>>> avoid unnecessary costs incurred from disruption of service, excessive 
>>> traffic, annoyances using up *my* time, and countless other reasonable 
>>> rationale from *my* point of view." Because sure, a few (hypothetical RIPE 
>>> probe) connections are exactly that, zero exaggeration, right?
>>> 
>>> In the end such fail2ban-fueled (or similar) behaviour I initially 
>>> addressed, is exactly a non-scientific extreme-case assumption-based 
>>> approach. There are better and even more standard ways. 
>>> 
>>> Crutch solutions out in the wild shouldn't be a showstopper for measuring 
>>> the ecosystem. (That is already quite neglected)
>>> 
>>> > What _objective_ risk/benefit analysis are you basing your opinions upon?
>>> 
>>> And you? What's the implication here about systems being as trigger-happy 
>>> as previously described?
>>> 
>>> Because sure, at some point rate limits make total sense, but certainly not 
>>> at the point where it would ban any potential RIPE probes.
>>> 
>>> >  Are you a systems administrator?
>>> 
>>> Let's not get into such measuring contests, even if it is the RIPE Atlas 
>>> mailing list.
>>> 
>>> On Tue, Sep 20, 2022 at 11:42 PM Paul Theodoropoulos via ripe-atlas 
>>> <ripe-atlas@ripe.net <mailto:ripe-atlas@ripe.net>> wrote:
>>> On 9/20/2022 10:45 AM, Avamander wrote:
>>>> Great to hear it works for you, but the potential unfortunate collateral 
>>>> from such a blanket action is not really RIPE Atlas' problem. There are 
>>>> more fine-grained methods against bruteforce attempts and open relay 
>>>> probes, than triggering on a few connections.
>>> What _objective_ risk/benefit analysis are you basing your opinions upon? 
>>> Are you a systems administrator? My responsibility is to avoid unnecessary 
>>> costs incurred from disruption of service, excessive traffic, annoyances 
>>> using up *my* time, and countless other reasonable rationale from *my* 
>>> point of view.  
>>> 
>>> You suggest that it is "not really RIPE Atlas' problem". That's very true. 
>>> And it is not really my problem if I bounce yoinky, pointless probes of my 
>>> server, and ruthlessly block them from contacting my server ever again. My 
>>> server, my choice, my wallet, nobody's business but my own.
>>>> Some webmasters ban IP's for simply visiting a domain, I know one that 
>>>> even dispatches an email to your ISP's abuse@ address upon visit. Should 
>>>> RIPE Atlas probes then not probe any HTTP servers? The answer is obviously 
>>>> no, they shouldn't care.
>>> Making arguments based upon extreme cases, assumptions, or 
>>> potential-for-collateral-damage is not scientific. "I know one that even 
>>> [...]" Anecdotal  evidence isn't scientific.
>>> 
>>> Note, I run a probe myself. I don't block any RIPE Atlas traffic on my 
>>> separate servers hosted on AWS, Oracle, and GCE. 
>>> 
>>> -- 
>>> Paul Theodoropoulos
>>> anastrophe.com <https://www.anastrophe.com/>-- 
>>> ripe-atlas mailing list
>>> ripe-atlas@ripe.net <mailto:ripe-atlas@ripe.net>
>>> https://lists.ripe.net/mailman/listinfo/ripe-atlas 
>>> <https://lists.ripe.net/mailman/listinfo/ripe-atlas>
>>> -- 
>>> ripe-atlas mailing list
>>> ripe-atlas@ripe.net <mailto:ripe-atlas@ripe.net>
>>> https://lists.ripe.net/mailman/listinfo/ripe-atlas 
>>> <https://lists.ripe.net/mailman/listinfo/ripe-atlas>
>> 
>> 
> 

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