Hello Thomas, and anyone else interested,

I've been having issues with both types of encrypted SMTP connections in 
ASSP. I believe they started sometime on or after build 13217. One 
aspect of the issue (#1) is that STARTTLS enabled connections will 
randomly stop working after the ASSP service has been running for a 
while. The error then sent to the mail client says: "An error occurred 
sending mail: Unable to establish a secure link with SMTP server 
smtp.XXXXX.com using STARTTLS since it doesn't advertise that feature. 
Switch off STARTTLS for that server or contact your service provider." A 
restart of ASSP will temporarily resolve the issue, and get the STARTTLS 
verb back for a time.

The other related issue (#2) that I am seeing is that SSL secured 
connections can usually send mail ok, as long as it doesn't have an 
attachment. It seems that emails with attachments (not sure this is 
exclusive, just what I've noticed), even if they were small attachments 
such as 100 KB or less, sometimes (usually after ASSP is running for a 
while) produced this error at the mail client: "Sending of message 
failed. The message could not be sent because the connection to SMTP 
server smtp.XXXXX.com was lost in the middle of the transaction. Try 
again or contact your network administrator". This error also adds the 
IP to the SSLfailed cache, and blocks any further attempts to send mail 
via SMTP, until it is removed from the cache.

Additionally, sometimes these attachments/larger emails just disappear 
and the recipient never gets them. The sender also does not get an error 
message about the failed transmission in their mail client. The email 
just appears to have been sent normally as far as they know. ASSP logs 
just make mention that the email is passing through and it's over 
/npSize/, and do not mention anything about blocking it. My mail server 
is also not doing any sort of blocking at all. But the mail just 
disappears. It's a fairly rare occurence but it has been noticeably 
happening, and to multiple, disparate, users as well. I suspect that the 
connection drops, as it does in the above error, but the error never 
gets sent back to the client, and the partial email cannot be sent on to 
its destination and so is destroyed. But the way this happens is that 
the user gets no notice that the mail did not actually get sent to its 
destination.

The latest issue (#3) is that now I cannot connect to SMTP with SSL/TLS 
at all, on any port (25, 465, 587). The connection just times out. This 
was after I had changed around my ASSP network config. Previously, I had 
all additional connections just going to/smtpDestination,/ but then, in 
an attempt to resolve the previous issues, I reconfigured and added 
separate destinations for /smtpDestinationSSL/ and /smtpAuthServer/. It 
might seem like a misconfiguration or that a server isn't listening, but 
STARTTLS works fine on these same ports. I previously was able to use 
SSL/TLS here though, and only switched to STARTTLS because of the #2 
SSL/TLS problems. All I am doing is proxying the connections, on the 
same port, to my mailserver (Exim) on 127.0.0.1. So externalip:465 
(ASSP) goes to 127.0.0.1:465 (Exim), and the same for the other ports. 
Also, the additional ports are setup the same way in Exim, so there's 
really nothing functionally different between the port 25 it was 
previously listening on and the newly added port 587/465.

Ok, I've now reversed the ASSP configuration just above, and went back 
to a single SMTP destination. All I did was change the ASSP config to 
remove the additional SMTP destinations (made the additional options 
blank, so it would revert to the main SMTP destination) and restarted 
ASSP. I just left my mailserver alone. But now I have SSL/TLS SMTP 
connections back. That behavior (losing the ability to make SSL/TLS 
connections) is not what I would expect from configuring those 
additional SMTP destination settings in ASSP though. Am I just missing 
some setting needed for this port configuration, or do you see this as well?

I noticed in the changelog for assp 2.3.4 build 13251 that "after 
upgrading IO::Socket::SSL and Net::SSLeay to the latest version sending 
blockreports, sync requests, notifications and resend mails using 
STARTTLS has been failed in some cases", and that sounded a lot like my 
STARTTLS issue, except with SMTP, so I wonder if it might be related? I 
don't remember exactly when I upgraded IO::Socket::SSL though.

Thanks in advance for investigating this. Please let me know if there's 
any more information that you need, or if you need me to try something 
out. I'm willing to do what I can to make ASSP better.

-C

--------------
Configuration:

I am aware of the SSLfailed cache and have been removing the ips from 
there when testing. Though I'm pretty sure it was only error #2 that 
added the ips to that cache.

Except for /DoTLS/, /SSLRetryOnError/, and the certificate settings, 
/SSL Proxy and TLS Support/ settings are set to the defaults.

Currently running ASSP version 2.3.4(13303) (Perl 5.014003) (on linux - 
Centos 5.10 64 bit)

OpenSSL is the default CentOS 5 RPM package, Version     : 0.9.8e 
Release     : 26.el5_9.1

Perl Modules:

Module Name     Module Version     Module Status     Download
show module load errors     installed / required(recommended)
ASSP_FC     disabled by Module Setup / 1.03     is disabled in config 
     CPAN
ASSP_SVG     disabled by Module Setup / 1.02     is disabled in config 
     CPAN
ASSP_WordStem     1.23 / 1.23     enabled     sourceforge
AsspSelfLoader     2.03 / 2.03     enabled     sourceforge
Authen::SASL     2.16 / 2.1401     enabled     CPAN
BerkeleyDB     disabled by Module Setup / 0.42     is disabled in config 
     CPAN
BerkeleyDB_DBEngine     / 4.5     status unknown     oracle
Compress::Zlib     2.061 / 2.008     enabled     CPAN
Convert::TNEF     0.18 / 0.17     enabled     CPAN
DB_File     disabled by Module Setup / 1.816     is disabled in config 
     CPAN
Digest::MD5     2.52 / 2.36_01     enabled     CPAN
Digest::SHA1     2.13 / 2.11     enabled     CPAN
Email::MIME     1.911 / 1.442     enabled     CPAN
Email::Send     2.198 / 2.192     enabled     CPAN
File::ReadBackwards     1.05 / 1.04     enabled     CPAN
File::Scan::ClamAV     disabled by Module Setup / 1.8     is disabled in 
config     CPAN
IO::Poll     0.08 / 0.07     enabled     CPAN
IO::Select     1.20 / 1.17     enabled     CPAN
IO::Socket::INET6     disabled by Module Setup / 2.67     is not 
detected (enableIPv6 is not set)     CPAN
IO::Socket::SSL     1.955 / 1.32     enabled     CPAN
LWP::Simple     6.00 / 1.41     enabled     CPAN
MIME::Types     1.38 / 1.23     enabled     CPAN
Mail::DKIM::Verifier     0.4 / 0.37     enabled     CPAN
Mail::SPF     2.008 / 2.007     enabled     CPAN
Mail::SPF::Query     1.999001 / 1.999001     enabled     CPAN
Mail::SRS     0.31 / 0.31     enabled     CPAN
Net::CIDR::Lite     0.21 / 0.20     enabled     CPAN
Net::DNS     0.72 / 0.61     enabled     CPAN
Net::IP     1.50 / 1.26     enabled     CPAN
Net::LDAP     disabled by Module Setup / 0.33     is disabled in config 
     CPAN
Net::SMTP     2.31 / 2.31     enabled     CPAN
Net::SMTP::TLS     disabled by Module Setup / 0.12     is disabled in 
config     CPAN
Net::SSLeay     1.55 / 1.35     enabled     CPAN
NetAddr::IP::Lite     1.50 / 1.47     enabled     CPAN
NetSNMP::agent     disabled by Module Setup / 5.05     is disabled in 
config     CPAN
PerlIO::scalar     0.11_01 / 0.05     enabled     CPAN
Regex::Optimizer     1.12 / 1.12     enabled     sourceforge
Regexp::Optimizer     disabled by Module Setup / 0.23     is disabled in 
config     CPAN
Schedule::Cron     1.01 / 0.97     enabled     CPAN
Sys::CpuAffinity     1.06 / 1.05     enabled     CPAN
Sys::MemInfo     0.91 / 0.91     enabled     CPAN
Sys::Syslog     0.33 / 0.25     enabled     CPAN
Text::Unidecode     0.04 / 0.04     enabled     CPAN
Thread::Queue     3.02 / 2.11     enabled     CPAN
Thread::State     0.09 / 0.09     enabled     CPAN
Tie::RDBM     0.73 / 0.70     enabled     CPAN
Time::HiRes     1.9725 / 1.9707     enabled     CPAN
Unicode::GCString     2012.10 / 2012.04     enabled     CPAN
threads     1.87 / 1.74     enabled     CPAN
threads::shared     1.43 / 1.32     enabled     CPAN
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