I created an issue:

https://merb.lighthouseapp.com/projects/7435-merb-more/tickets/35-cannot-send-mail-via-smtp-to-multiple-recipients

<https://merb.lighthouseapp.com/projects/7435-merb-more/tickets/35-cannot-send-mail-via-smtp-to-multiple-recipients>I
also included a revised change that should (1) be compatible with Ruby 1.9
and (2) handle the case where @mail.to is a String.

..tony..

On Sat, Apr 24, 2010 at 2:33 PM, Pavel Kunc <[email protected]> wrote:

> Being all that said, I actually think it deserves Lighthouse issue,
> please create one.
>
> Pavel
>
> On Apr 24, 10:25 pm, Pavel Kunc <[email protected]> wrote:
> > Hi Tony,
> >
> > Being the author of the change I explain my rationale behind it.
> >
> > The old Merb code is not correct either because it doesn't work in
> > Ruby 1.9.1. The behaviour of Array#to_s did change and so the old Merb
> > code didn't work at all.
> >
> > The @mail.to.to_s.split() is also unnecessary if the @mail.to array
> > would look like ['email', 'email'], than you can pass it directly to
> > the send_message(). However it seems that code is there to catch cases
> > like ['email, email', 'email'] to become and array of three elements.
> > Which actually seems like your case.
> >
> > Also the fact that the MailFactory does return only array might be
> > true but using merb_exceptions I found that the @mail.to can actually
> > be string in some circumstances. I don't remember, it's some time so
> > we can revisit this, if that is not true than we could actually make
> > all work on all Rubies with something like:
> >
> > @mail.to.join(',').split(/[,;]/)
> >
> > I have no problem resolving the issue to some state which will work on
> > 1.8.x and 1.9.x and for merb_exceptions :-)
> >
> > Pavel
> >
> > On Apr 14, 8:10 pm, Tony Mann <[email protected]> wrote:
> >
> >
> >
> >
> >
> > > Currently, merb-mailer 1.1 will not properly support a comma-separated
> list
> > > of addresses nor an array of addresses if you are using SMTP. Here is
> why:
> >
> > > MailFactory has a bug that prevents it from supporting an array of
> > > addresses. If you try to use an array, the addresses get smashed
> together.
> > > The problem is in their add_header method:
> >
> > > def add_header(header, value)
> > >     value = quoted_printable_with_instruction(value, @charset) if
> header ==
> > > 'subject'
> > >     value = quote_address_if_necessary(value, @charset) if %w[from to
> cc bcc
> > > reply-to].include?(header.downcase)
> > >     @headers << "#{header}: #{value}"
> > > end
> >
> > > The quote_address_if_necessary call handles an array, but then it gets
> > > converted into a string when added to @headers. Oops.
> >
> > > So, MailFactory requires that you pass in a comma-separate list.
> However,
> > > later on in merb-mailer, we have this code:
> >
> > > smtp.start(config[:domain], config[:user], config[:pass],
> config[:auth]) {
> > > |smtp|
> > >     to = @mail.to.is_a?(String) ? @mail.to.split(/[,;]/) : @mail.to
> > >     smtp.send_message(@mail.to_s, @mail.from.first, to)
> >
> > > }
> >
> > > Unfortunately, this will not work, because @mail.to is never a String!
> Why?
> > > Because MailFactory always returns an array with one item in it (to
> support
> > > multiple headers with the same tag). As mentioned above, the single
> item in
> > > that array is always a String. So the whole check is no good and
> > > unnecessary. The old merb-mailer code looked like this:
> >
> > > smtp.start(config[:domain], config[:user], config[:pass],
> config[:auth]) {
> > > |smtp|
> > >     smtp.send_message(@mail.to_s, @mail.from.first,
> > > @mail.to.to_s.split(/[,;]/))
> >
> > > }
> >
> > > This is correct code, and the 1.1 code should be reverted to this.
> >
> > > Now, I have not posted a Lighthouse ticket quite yet, because I am
> afraid I
> > > am missing something. Per above, merb-mailer 1.1 breaks sending mail
> via
> > > SMTP to multiple recipients, and I find it hard to believe no one else
> has
> > > encountered this issue yet. Can anyone enlighten me?
> >
> > > ..tony..
> >
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