Redmine

it's a bug, but since the mail gem maintainer is inactive for a long time, I don't expect any fixes soon.

you have 2 options:
1/ use SSL
2/ apply an unofficial patch, see https://github.com/mikel/mail/pull/1435

Try this:

production:
  email_delivery:
    delivery_method: :smtp
    smtp_settings:
      address: xxxxxxx
      port: 25
      disable_start_tls: true
      openssl_verify_mode: "none" 

After upgrade to redmine 5.0 i have encountered the same issue. Config above managed to fix it without modifying mail gem.

Thanks pavel ochman & Dmitry K - I think I'll have to try to modify the gem. I tried pasting Dmitry's config but the result is the same - there must be a difference in our SMTP servers.

I've forked a branch from mail 2.8.0-stable and added jeremy's patch in there, with one fix.

In case it ever helps anyone, just clone this and build the gem.
https://github.com/GChuf/mail/tree/2-8-stable

git clone https://github.com/GChuf/mail/
git checkout 2-8-stable
cd mail
gem build mail.gemspec
gem install mail -v2.8.0.patch

After that, change the mail version in redmine's Gemfile.

FYI there's a breaking change in 2.8 https://github.com/redmine/redmine/blob/master/app/models/mail_handler.rb#L528

Mail::RubyVer.pick_encoding(p.charset).to_s

Mail::Utilities.pick_encoding(p.charset).to_s

but it may not affect you unless you're a helpdesk user

Thanks Pavel,

helpdesk as in redmine helpdesk plugin?

In any case - it makes sense to patch the 2.7. branch and use that, then.

I meant this https://www.redmine.org/projects/redmine/wiki/redminereceivingemails

Thanks for all the help.
I created a patched branch of 2-7-stable as well (2.7.2).

https://github.com/GChuf/mail/tree/2-7-stable

Pavel Rosický wrote:

you have 2 options:
1/ use SSL
2/ apply an unofficial patch, see https://github.com/mikel/mail/pull/1435

Hi,
I just stumbled over the same problem after upgrading to redmine-5.0.4, and after some hours, I just wanted to share my (pretty simple) solution:

Follow Pavels suggestion #1 and just switch SSL ON (if you are able to relay to one of your servers via port 25, you as well are able to relay via port 465 (smtps).

So I did the opposite I initially planned and switched all ON

email_delivery:
    delivery_method: :smtp
    smtp_settings:
      address: "<server-ip-address>" 
      port: 465
      ssl: true <-no idea wether this does anything
      tls: true <-no idea wether this does anything
      disable_start_tls: false <-no idea wether this does anything
      enable_starttls_auto: true
      openssl_verify_mode: "none"

Works like a charm

Hi Donald,
the issue was, you can't disable starttls even with an explicit enable_starttls_auto: false due to incompatibility between the mail gem and the new net/smtp that enables starttls by default.

as a workaround, you can use SSL as you did, but the original author was trying to avoid it for some reason...

note that, this issue is fixed by #37993 (redmine 5.1+ only)

Hi Pavel,
first, thanks for your answwer and for the fix in 5.1!

I totally understood the issue, I just tried to point out the simpest way to get along with the problem if you install redmine 5.0.4 on your servers.

If you just enable ssl in the settings (and your server accepts 465 (all smtp-servers do)), you dont have anything more to do in 5.0.4.
No patches to be installed, no rb files to be changed, no certifidates to be installed - it just worked out of the box with just ssl on on my side.

Thats why I posted this workaround for desperate and (considering ruby and rails) totally clueless system admins :)