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Despite finding other posts about this online, I cannot seem to get a resolution for my setup. I'm using Ubuntu 14.04 on AWS. All I need this server to do is send an email (with a .PDF attachment) via ZOHO's mail server. The problem is that ZOHO's mail server requires SSL, there's no way around it. This is apparently a known bug in Debian: https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=679911 However, I can't find a consensus on how to fix it, the Debian bug page just says to not use SSL, which isn't possible since I'm using ZOHO and can't change mail providers at this time.

I have been using a Linux Mint 17.3 VM for this task, so I know for a fact it is possible, but that particular VM cannot be used for this any longer (for reasons too lengthy to go into).

This is what I have tried so far:

  • sudo update && upgrade (and I also tried running the commands one at a time)
  • updating Perl 5 via the commands sudo cpan cpan[1]> upgrade

  • Deploying Ubuntu Server 16.04 instance on AWS instead (no difference except error list different line of the /usr/share/perl5/IO/Socket/SSL.pm file)

Can someone please tell me what edits to make with Nano to fix this and to what files? I'm a Windows SysAdmin, so Linux is not my strong suit.

2 Answers 2

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The underlying problem is a bug in the old and for 10 years unmaintained Net::SMTP::TLS module. See invalid SSL_version specified at /usr/local/share/perl5/IO/Socket/SSL.pm line 598 what need to be changed.

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  • Thanks, Steffen. I did see this and attempt to make the changes with nano, but for whatever reason they did not work for me. Oct 5, 2016 at 12:52
  • With my new AWS Ubuntu 14.04 instance that is working, I do not actually even have the folder where the error was pointing to before: usr/local/share/perl5 Oct 5, 2016 at 14:42
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I was able to find a resolution by deleting this faulty AWS instance and deploying a new one, again of Ubuntu Server 14.04, only this time I followed these instructions to get sendEmail going: https://ubuntuforums.org/showthread.php?t=1127478

sudo apt-get install sendemail
sudo apt-get install libio-socket-ssl-perl

I assume that my problem was with the old command I was using to install perl5 before (but don't know for sure, or if so, why):

apt-get install libio-socket-ssl-perl libnet-ssleay-perl perl

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