Re: [mailop] Microsoft/Outlook contact for *.outbound.protection.outlook.com

2024-06-28 Thread Alexander Huynh via mailop
> Microsoft is trying (over and
> over) to send me emails, and they get past connect/disconnect.  This has
> been going on for a few days now, at a rate of once every 5 seconds.

I also experience this. In the past, I've filed a support request with 
Microsoft asking for an explanation, but haven't received a satisfactory answer.

An analysis of what I see shows:
* no emails are sent, just a connect/STARTTLS/disconnect
* the connecting IPs change

Combined with when this started happening for me:
* after I started blocking (at the SMTP level) selective spam emails 
originating from Microsoft's infrastructure

Leads me to believe that these are health probes to try and check 
deliverability.

I'm happy to be corrected/enlightened by more information.
-- 
Alex 
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop


Re: [mailop] "The email didn't arrive" to Office 365

2024-05-09 Thread Alexander Huynh via mailop
Statistics and debugging options are more limited on the sender to Microsoft 
side, but if you have an amenable recipient or an amenable admin on the 
recipient's side, requesting them to initiate a message trace should yield 
specifics on message deliverability.

https://learn.microsoft.com/en-us/exchange/monitoring/trace-an-email-message/trace-an-email-message
--
Alex
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop


Re: [mailop] Debt Collection Client Email Servers

2024-03-26 Thread Alexander Huynh via mailop
On Mar 26, 2024, at 09:14, Chris Adams via mailop  wrote:

I recently started getting debt collection emails [...] And there's no 
"unsubscribe" or "this is not me"...

Good news is there's a draft RFC presented at IETF 119 to tackle this: 
https://datatracker.ietf.org/doc/draft-dweekly-wrong-recipient/
--
Alex
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop


Re: [mailop] [spamhaus] de-listing requests successful, but only for a couple of days.

2024-03-14 Thread Alexander Huynh via mailop
Would you consider your own /64 or /48 from RIPE?

It's one way of being in control of your own reputation.
-- 
Alex
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop


Re: [mailop] Anyone else noticing an increase in spam from Office365 distribution lists?

2024-01-14 Thread Alexander Huynh via mailop
From a spam point of view, signing up for a domain is a barrier of entry 
which some may consider too much trouble.


This may play into why there's a larger distribution of unwanted mail on 
the freely-provided `*.onmicrosoft.com` subdomains.

--
Alex
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop


Re: [mailop] Gmail SMTP timeouts

2023-04-13 Thread Alexander Huynh via mailop

Are you running exim?

I have the following in my config, which seems to help the issue:

# disable TCP fast open for gsmtp servers, due to a kernel bug; the bug was 
supposedly
# fixed in 5.18, but it seems there's still some quirkiness with gmail 
without this
# setting
#
# 
https://www.chromosphere.co.uk/2022/06/01/googles-tcp-fast-open-breaks-exim-delivery/
# 
https://forum.hestiacp.com/t/gmail-smtp-timeout-after-sending-data-block-connection-timed-out/4745/75
# 
https://github.com/myvesta/vesta/commit/c7aa6ec7494bc3b7ac4885182383c1bf88692c1b
hosts_try_fastopen = !*.l.google.com : !*.googlemail.com : *

Good luck,
--
Alex
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop


Re: [mailop] Intuit directly spaming

2023-03-04 Thread Alexander Huynh via mailop

On 2023-03-04 22:58:23 +, MRob via mailop wrote:

Thanks you Atro, is there popular tool for to do that in real time?


There's also https://bgp.tools/, made by a friend and former colleague.
--
Alex
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop


Re: [mailop] Spam received from ips with forged reverse names

2023-01-05 Thread Alexander Huynh via mailop
On Jan 5, 2023, at 14:54, Serizy via mailop  wrote:

but what worries me is that, the PTR resolves to the fake hostname, but the 
host name doesn’t resolve to the ip, logically…and the messages go to the user 
mailbox in Outlook.com

This should not be an issue if the MTA performs both forward (A//CNAME) and 
reverse (PTR) DNS validation.

Is there any way to report this?

Others may correct me, but I believe the channels for reporting abusive PTR 
records lie with the body who owns those IPs. A WHOIS on the offending IPs 
should provide an abuse contact.

Shouldn’t be even legal I think.

Legal or not, that may not prevent people from doing so, as evidenced here, nor 
may incentivize people to rectify these abuses.
--
Alex
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop


Re: [mailop] How do I break Gmail forwarding?

2022-10-24 Thread Alexander Huynh via mailop
Block it at the receiving end.
-- 
Alex
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop


[mailop] Apple contact for strange email

2022-10-18 Thread Alexander Huynh via mailop

Hello,

I've been seeing a few mail connection attempts from Apple's IP space, 
which I've been rejecting due to mismatched A /  and PTR records 
(see sample log at the end, times UTC).


Is there anyone at Apple who can contact me off list?

Thanks,
--
Alex

Oct 10 11:39:35 H=[17.240.49.64]:18357 rejected connection in "connect" 
ACL: host lookup failed (17.240.49.64 does not match any IP address for 
mr52p01nt-msbadger008105.ise.apple.com)
Oct 11 11:33:50 H=[17.240.49.39]:35629 rejected connection in "connect" 
ACL: host lookup failed (17.240.49.39 does not match any IP address for 
mr45p01nt-msbadger005101.ise.apple.com)
Oct 12 11:42:46 H=[17.240.49.58]:55433 rejected connection in "connect" 
ACL: host lookup failed (17.240.49.58 does not match any IP address for 
mr52p01nt-msbadger007106.ise.apple.com)
Oct 13 11:27:15 H=[17.240.6.32]:25397 rejected connection in "connect" ACL: 
host lookup failed (17.240.6.32 does not match any IP address for 
st57p01nt-msbadger004101.ise.apple.com)
Oct 15 12:35:44 H=[17.240.49.48]:37100 rejected connection in "connect" 
ACL: host lookup failed (17.240.49.48 does not match any IP address for 
mr52p01nt-msbadger006103.ise.apple.com)
Oct 17 11:36:12 H=[17.240.49.33]:12835 rejected connection in "connect" 
ACL: host lookup failed (17.240.49.33 does not match any IP address for 
mr45p01nt-msbadger004102.ise.apple.com)
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop


Re: [mailop] EC certs in MTA - MTA TLS

2022-08-22 Thread Alexander Huynh via mailop

On 2022-08-22 16:07:33 +0200, Slavko via mailop wrote:

Please, can you elaborate more from where the cipher suites mismatch
was coming? I mean if it was (your) server or the remote side, which
provided/requested them.


My mail server as the server, and my bank's mail server as the client, 
for example.

--
Alex
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop


Re: [mailop] EC certs in MTA - MTA TLS

2022-08-21 Thread Alexander Huynh via mailop

On 2022-08-21 19:46:31 +, Slavko via mailop wrote:

Is that typo? AFAIK both these cipher suites are usable only
with RSA certificate, they difers only by ephemeral key exchange
algo...


Sorry, you're right that it's a typo. I just re-tested and want to 
clarify that: ECDHE-RSA-AES128-GCM-SHA256 is exclusive to RSA 
certificates, and ECDHE-ECDSA-AES128-GCM-SHA256 is exclusive to EC 
certificates, which is less widely supported by other MTAs.


I've hobbled up a script to enumerate ciphersuites at 
https://gist.github.com/ahrex/8d2c15086a116bb9388424c40687f20f, which 
you can use to scan your local MTA to see what it supports as a server.  
You may also try this on remote MTAs, though they may not be as friendly 
to scans. Of course YMMV, since there's no guarantee that ciphersuites 
presented by remote MTAs as a server are the same as what's supported 
when they're a client connecting to you, so .pcaps are the best way to 
tell.


Thanks for spotting my typo,
--
Alex
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop


Re: [mailop] EC certs in MTA - MTA TLS

2022-08-21 Thread Alexander Huynh via mailop

On 2022-08-21 12:35:18 +0200, Slavko via mailop wrote:

if there are known some issues with ECcerts.


Yes, there are. I ran the exact setup you described, and I had to debug 
a whole slew of cipher suite mismatches, bringing out tcpdump and 
Wireshark.


The gist of my debug came down to: the nature of your certificate 
partially determines what cipher suites you may use, e.g. 
DHE-RSA-AES256-SHA256 and ECDHE-RSA-AES256-SHA256 are mutually 
exclusive, with the former only being available to RSA certs, and the 
latter only being available to EC certs.


Guess which cipher suites are advertised more often during the TLS 
handshake.


For me, the issue took a little time to discover, since mail can fall 
back to unsecured transmission if TLS negotiation fails, which is how I 
originally noticed there was an issue.


My suggestion is to stick to an RSA cert for now, and wait for larger 
mail server adoption of TLS 1.3. There's a smaller cipher suite list in 
TLS 1.3, which would allow for more overlap opportunity between what you 
offer, and what the other side accepts.

--
Alex
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop


Re: [mailop] Microsoft Office365 blocking non Oauth2 authentication on IMAP and SMTP.

2022-08-20 Thread Alexander Huynh via mailop
Shameless plug: this discussion has gotten me to open-source my Office 
365 OAuth script, which should be plug-and-play compatible with mail 
systems that can run python3 scripts and receive XOAUTH2 JWTs via stdin.


If you'd like to give it a try, visit 
https://github.com/ahrex/oauth-helper-office-365


There's an example mutt integration, which I'm currently using to 
compose this very email.


Have a good one,
--
Alex
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop


Re: [mailop] Russian crypto phish campaign via sendgrid to stolen Robinhood account

2022-04-24 Thread Alexander Huynh via mailop
On Apr 24, 2022, at 23:09, John R Levine via mailop  wrote:

Anyone else seeing this?

I’ve received a similar spam email supposedly from Metamask almost a month ago, 
from an O365 tenant to my O365 tenant: https://pastebin.com/Tb3S8BuD

There are slight differences in the email I received:
  * the headers imply Mailgun instead of SendGrid
  * the sending IP was O365, unrelated to Mailgun itself
--
Alex
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop


Re: [mailop] Is there any cloudflare staff here?

2022-04-20 Thread Alexander Huynh via mailop
Reaching out off-list.
-- 
Alexander Huynh
R, Cloudflare
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop


Re: [mailop] Odd delay at Gmail ?

2022-04-20 Thread Alexander Huynh via mailop
On 2022-04-20 12:51:47 +0200, Cyril - ImprovMX wrote:
> What happened here ?

Anecdotally, I recently switched MX servers and found that my emails
from Google were also delayed for about 8 hours. The next day when I
received my MTA-STS reports, I found 53 failures as reported by Google,
since my then MTA-STS policy did not include the new MX server. While I
can't say your issue is due to MTA-STS cache invalidation, I would
suggest checking the various nuts and bolts both internally, and using
external validators.

Hope this helps,
-- 
Alex
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop


Re: [mailop] Best mailbox provider for personal domain?

2022-04-10 Thread Alexander Huynh via mailop
> On Apr 10, 2022, at 10:40, Byron Lunz via mailop  wrote:
> 
> I don't recall seeing any discussion in this thread about how to migrate old 
> email messages from a Google Workspace account to a different host. Anyone 
> have advice or suggestions on how to do that? 

You could use https://takeout.google.com/ to download an mbox format.

Querying "gmail api export eml site:github.com" into Google yields alternative 
methods for downloading a whole inbox using the Gmail API, but answers there 
are a bit old and might need some manual work.
-- 
Alex
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop


Re: [mailop] Exchange 365 outbound connector being used as a relay

2022-01-29 Thread Alexander Huynh via mailop
On 2022-01-29 09:15:02 +, Matthew Richardson via mailop wrote:
> As a thought (probably wrong) could this be caused by your O365 users
> forwarding INCOMING email to them FROM outlook.com and/or mail.alokind.com
> to external addresses?

Since all mail flows through Exchange 365, O365 would have to allow my users to 
preserve
the FROM address, which seems like a security flaw. The only reasonable time 
I've seen
this preservation is for forwarded calendar invites, which in my exim config 
have their
own special rewrite rules, and did not trigger.

Side note: forwarded calendar invites break DKIM due to this preservation.

> >  * Are there any safeguards in place from preventing one tenant from using 
> > another
> >tenant's connectors?
> 
> It is not certain that this is what is occurring.  For example, your setup
> would not preclude other tenants pointing their outgoing email to your Exim
> (not that this would be sensible for them).

Precisely! I'm looking for restrictions on O365's end to prevent another tenant 
from
using my connector. I have yet to find any, but maybe I'm not looking hard 
enough.

> You may wish to have some authentication between O365 and Exim.  The MS
> document linked discusses how to do this with certificates.

The certificate setup listed at that page did not provide settings for outbound
connector client certificates. From what I've found and done, I've set up a 
server-side
certificate, which is used for legitimate connections (times UTC, fields 
obfuscated):

Jan 29 14:04:54 webmail exim[2482103]: 1nDoLW-00APhv-Bk <= a...@e.sc 
H=mail-dm6nam12lp20206.outbound.protection.outlook.com 
(NAM12-DM6-obe.outbound.protection.outlook.com) [2a01:111:f400:fe59::206]:17704 
P=esmtps L. X=TLS1.2:ECDHE_SECP384R1__ECDSA_SHA256__AES_256_GCM:256 CV=no 
SNI=ipv6.e.sc K S=162589 M8S=0 RT=0.202s 
id=79e8610b9a6e43c29cf1833a821ed...@mn2pr08mb6272.namprd08.prod.outlook.com 
T="FW: BBB" from  for c...@ddd.ee

Comparing that to the fields in the original blocked connection:

Jan 28 10:38:40 webmail exim[2145158]: 
H=mail-mw2nam10olkn2087.outbound.protection.outlook.com 
(NAM10-MW2-obe.outbound.protection.outlook.com) [40.92.42.87]:62109 
X=TLS1.2:ECDHE_SECP384R1__ECDSA_SHA256__AES_256_GCM:256 CV=no rejected MAIL 
: prohibited sender domain

There are these things to note from exim's log format [0]:

  * TLS was negotiated in both cases: `X` field
  * no `SNI` was provided in the blocked case
  * no client certificate valiation was done from exim to O365: `CV` field

The `CV` field is the last thing I can control, but I don't believe that 
provides any
authentication of valid email domains, only a lesser authentication that it's 
O365
connecting to me, which is already guaranteed by the IP ACLs.

I appreciate the look,
-- 
Alex

[0] https://www.exim.org/exim-html-current/doc/html/spec_html/ch-log_files.html
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop


[mailop] Exchange 365 outbound connector being used as a relay

2022-01-28 Thread Alexander Huynh via mailop
Hello all,

This info may be better reserved for a Microsoft support ticket, but I figure 
there are
a few people here who could help short circuit the process, or offer insight 
into my
issue.

My mail service currently uses Exchange 365 as the data store, with an exim 
outbound
connector [0] hosted on AWS infra.

The setup for outbound mail is as follows:

MUA --> Exchange 365 MTA --> connector MTA --> Internet

I've added ACLs on my connector to only accept port 25 TCP traffic from 
Exchange 365 IPs
[1], and added an allowlist on my connector MTA to only accept mail for domains 
I own.

During some log spelunking, I've received 3 curious entries (times UTC):

Jan 28 10:38:40 webmail exim[2145158]: 
H=mail-mw2nam10olkn2087.outbound.protection.outlook.com 
(NAM10-MW2-obe.outbound.protection.outlook.com) [40.92.42.87]:62109 
X=TLS1.2:ECDHE_SECP384R1__ECDSA_SHA256__AES_256_GCM:256 CV=no rejected MAIL 
: prohibited sender domain
Jan 28 21:52:03 webmail exim[2281852]: 
H=mail-ma1ind01hn2225.outbound.protection.outlook.com 
(IND01-MA1-obe.outbound.protection.outlook.com) [52.100.187.225]:5171 
X=TLS1.2:ECDHE_SECP384R1__ECDSA_SHA256__AES_256_GCM:256 CV=no rejected MAIL 
: prohibited sender domain
Jan 28 23:22:58 webmail exim[2300338]: 
H=mail-bmxind01hn2226.outbound.protection.outlook.com 
(IND01-BMX-obe.outbound.protection.outlook.com) [52.100.219.226]:17370 
X=TLS1.2:ECDHE_SECP384R1__ECDSA_SHA256__AES_256_GCM:256 CV=no rejected MAIL 
: prohibited sender domain

Meaning that domains `outlook.com` and `mail.alokind.com` have managed to use 
Exchange
365 infrastructure to try and route email through my connector.

My questions are:

  * Is this expected?
  * Are there any safeguards in place from preventing one tenant from using 
another
tenant's connectors?
  * (!) `outlook.com` was somehow routed to my connector, how did that happen?
  * What are the suggested methods for preventing other tenants from using 
connectors
with IP allowlists (i.e. are domain allowlists the way to go, are there 
other
methods)?

Thanks,
--
Alex

[0] 
https://docs.microsoft.com/en-us/exchange/mail-flow-best-practices/use-connectors-to-configure-mail-flow/set-up-connectors-to-route-mail
[1] 
https://docs.microsoft.com/en-us/microsoft-365/enterprise/urls-and-ip-address-ranges
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop