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 ------------------------------------------------------------------------------ DreamFactory - Open Source REST & JSON Services for HTML5 & Native Apps OAuth, Users, Roles, SQL, NoSQL, BLOB Storage and External API Access Free app hosting. 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