SSLDEBUG at the highest level will show something like that in maillog.txt

Aug-3-21 16:53:15 [Worker_1] Worker_1 wakes up
Aug-3-21 16:53:15 [Worker_1] Info: Worker_1 got connection from MainThread
Aug-3-21 16:53:15 [Worker_1] Connected: session:114507858 a.b.c.d:52084 > 
e.f.g.h:25 > 127.0.0.1:325
Aug-3-21 16:53:16 [Worker_1] a.b.c.d [SMTP Reply] 220 mail.thockar.com is 
ready - using ASSP 2.6.6(21202)
Aug-3-21 16:53:16 [Worker_1] a.b.c.d [SMTP Reply] 250 HELP
Aug-3-21 16:53:16 [Worker_1] a.b.c.d info: got STARTTLS request from 
a.b.c.d
Aug-3-21 16:53:16 [Worker_1] a.b.c.d [SMTP Reply] 220 Ready to start TLS - 
go on
Aug-3-21 16:53:16 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:1620: start 
handshake
Aug-3-21 16:53:16 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:1177: global 
error: Undefined SSL object
Aug-3-21 16:53:16 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:1061: 
starting sslifying
Aug-3-21 16:53:16 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:1109: 
Net::SSLeay::accept -> -1
Aug-3-21 16:53:16 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:1109: 
Net::SSLeay::accept -> -1
Aug-3-21 16:53:16 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:1109: 
Net::SSLeay::accept -> 1
Aug-3-21 16:53:16 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:1157: 
handshake done, socket ready

and for web connections for example

Aug-3-21 16:59:23 [Main_Thread] Info: SSLCertVerify - SSLWEBCertVerifyCB: 
callback returned: 1
Aug-3-21 16:59:23 [Main_Thread] Info: SSLCertVerify - SSLWEBCertVerifyCB: 
callback returned: 1
Aug-3-21 16:59:23 [Main_Thread] Info: (1) person 'Thomas Eckardt' located 
in 'DE//', email address '', logged in as 'root'
Aug-3-21 16:59:23 [Main_Thread] Info: SSLCertVerify - SSLWEBCertVerifyCB: 
callback returned: 1
Aug-3-21 16:59:23 [Main_Thread] Adminuser root authenticated for admin 
connection for page / using a valid certificate owned by Thomas Eckardt ,
Aug-3-21 16:59:23 [Main_Thread] Admin connection from user root on host 
a.b.c.d:53757; page:/; session-ID:3c791f4f2ab58119fc9d109ed978f6e1;


ConTimeoutDebug

generates the con....txt files in the debug folder. These files show, what 
was going on in the connection until the timeout was reached.


Exclude these IP's from SSL-failed-Cache* (noBanFailedSSLIP) - may help 
(there is no need to restart assp !)

the SSL-failed cache can be cleared or manipulated using the left menu in 
the GUI -> below 'internal Caches' (scroll to the bottom)


gentoo:

One of the systems I maintain is running a gentoo (what a horror OS!). 
ASSP autoupdates to the latest public available dev version. This system 
runs without a single manual intervention for months now. Assp does a 
service autorestart ones in a week.
How ever, system components, perl and perl modules are still untouched for 
over 18 months.

for the records:

after reseting all STATS a week ago on my prod windows system, I got no 
timeouts - even not a single one from the big mailers.
SMTP SSL-Port-Connections Timeout:      0       0
SMTP STARTTLS-Connections Timeout:      0       0

perl modules in use:

IO::Poll        1.45
IO::Select      1.45
IO::Socket::INET6       not installed
IO::Socket::SSL 2.071

Net::SSLeay     1.90
OpenSSL 1.1.1i
OpenSSL-lib 1.1.1i 8 Dec 2020

system info:

Server OS:      Windows Server 2016
Perl Version:   5.032001
physical-memory:        20479 MB 
free physical-memory:   8781 MB 
total virtual-memory:   24319 MB 
free virtual-memory:    8528 MB 
assp-process-memory:    current: 3690 MB        min: 999 MB     max: 6967 
MB
Number of CPU's:        6 
ASSP Version: (dev) 2.6.6 build 21202


Thomas



Von:    "William L. Thomson Jr." <wlt...@o-sinc.com>
An:     "For Users of ASSP" <assp-user@lists.sourceforge.net>
Datum:  03.08.2021 16:42
Betreff:        Re: [Assp-user] STARTTLS - connection randomly timeout 
(outlook imap error)



On Tue, 3 Aug 2021 12:53:29 +0200
Thomas Eckardt <thomas.ecka...@thockar.com> wrote:
>
> This will not help. ASSP uses standard libs for SSL/TLS
> (IO::Socket::SSL -> Net::SSLeay -> openssl-lib !

Would newer versions of that cause issue? Or maybe other perl related
stuff.

I have updated perl but not much else, and perl atm is a total mess in
Gentoo. Sadly, main perl guy passed away, and the others are trying to
step in, but its not a good situation. However, it does not seem to
affect any other aspects of ASSP, so would be pretty odd to just affect
a few sometimes, with those few being big emailers.

I cannot track down this issue relating to any specific update or
period of time for updates.


> >It is not good situation at production server.
> 
> If openssl was upgraded, I recommend to read the release notes. If
> postfix was upgraded, .. the same. Such readings and upgrade planing
> are done by an IT-department before system upgrades are done!
> If you have any doubt about upcoming problems, all upgrades needs to
> be tested in a test environment BEFORE they are going in to
> production mode.

I have run ASSP for several decades, never seen any issues like this,
and seems semi sporadic as emails do come through at times, but the
majority do not. I have done a lot of major upgrades on the systems
ASSP runs on, gentoo being rolling.

> IMHO - most of these problems are related to the usage of self signed 
> certificates, outdated certificates, unchained certificates, missing 
> intermediate certificates in chains, allowed weak cipher suites,
> allowed weak SSL protocols, too weak RSA keys 

I do believe they are increasing things on the other end, at first I
thought maybe TLS 1.3, so I patched and updated qmail. But I have two
different setups going, patched qmail for TLS 1.3, and the older TLS
patched qmail, and both exhibit the same, so I am not confident it is
the MTA at all, seems like ASSP or some underlying perl/openssl issue
maybe.

> openssl as well as postfix (and many other products) are working hard
> to secure their applications. Some or all of the above faults may
> lead in to more and more problems with every new software release.
> Most times there are temporary workarounds available (openssl.cnf , 
> master.cnf .....), if the default security is increased in new
> releases. Notice: peers using new software releases may reject
> connection to or from older releases, because of the availability of
> "unsecure" communication options! So, the workarounds may not solve
> all your problems.

It is possible, but seems odd that it would affect only some, and some
of the time. It seems like there is something happening or not
happening as part of the connection establishment.

> 
> SSLDEBUG and ConTimeoutDebug may help to get some more information
> from assp.

What options will increase output here?

I have increased SSLDebug but not changing these messages. This shows
the issue, this is from Google/Gmail. Also seems to only affect
TLS-in/TLS-out, but that does work from other providers.

Aug  3 03:08:24 mail assp.pl[1373]: [Worker_3] [TLS-in] [TLS-out]
2607:f8b0:4864:20::73d TLS-Connection idle for 180 secs - timeout
Aug 3 03:08:24 mail assp.pl[1373]: [Worker_3] [TLS-in] [TLS-out]
2607:f8b0:4864:20::73d [SMTP Status] 451 Connection timeout, try later
Aug  3 03:08:24 mail assp.pl[1373]: [Worker_3] [TLS-in] [TLS-out]
2607:f8b0:4864:20::73d disconnected: session:7FDE3DC448A0
2607:f8b0:4864:20::73d - processing time

> btw.: I use certificates from letsencrypt and I never had any SSL/TLS 
> problems. I update the perl modules at least once a week from CPAN. 
> openssl is upgraded once in a year (together with the new perl
> version). I use every time the (my) latest assp development version
> on my production system.

I also use letsencrypt, I have for a few years, certs are auto renewed
monthly. This issue started about 3-4 months back. First with Amazon
and Google, and then others, eBay, Microsoft/Outlook, and others.

I think ~25% or more of the email is not arriving in general, and from
those providers, more like 80% or more is not arriving.

I really hope this can be resolved someway. I would hate to not run
ASSP, I have not lived that way for a very very long time. No clue what
an alternative to ASSP might be, or the potential issues, etc. ASSP
replaced a horrendous Spamassassin+ other stuff back in the day that
used a ridiculous amount of memory and CPU per email. ASSP has been a
godsend!

Thanks for keeping it going Thomas!!!

-- 
William L. Thomson Jr.


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