I believe that this is due to gmail not allowing the email.  I think
there are two ways to fix this:

1.  Temporarily enable less secure apps for your gmail account while
you send the email [see
here](https://support.google.com/accounts/answer/6010255?hl=en).
2.  Setup multi-factor authentication on your account and create an
app specific password for git-send-email [see
here](https://support.google.com/accounts/answer/185833?hl=en)

Obviously the second method is more secure.  I have had success with
both of these techniques.

On Wed, Jul 15, 2015 at 1:11 AM, Juston Li <juston.h...@gmail.com> wrote:
> Hello
>
> Recently, I have had trouble using git send-email to send a patchset.
> After the confirmation to send the email I get the following:
> Send this email? ([y]es|[n]o|[q]uit|[a]ll): y
> [Net::SMTP::SSL] Connection closed at /usr/lib/git-core/git-send-email
> line 1320.
> fatal: 'send-email' appears to be a git command, but we were not
> able to execute it. Maybe git-send-email is broken?
>
> This message first appeared when I tried to send a 19 commit patchset
> via 'git send-email HEAD~19'. It also fails when I try to format-patch
> and send the patchset separately via 'git send-email 0001...'
> Oddly enough, it works when I send anything other than 19 commits
> for example 'git send-email HEAD~1' or 'git send-email HEAD~20'
>
> I thought it was something with the gmail servers but I was able to send
> the patchset by downgrading a couple perl packages
> warning: downgrading package perl (5.22.0-1 => 5.20.2-1)
> warning: downgrading package perl-net-ssleay (1.68-2 => 1.67-1)
>
> Note perl-net-ssleay depends on perl 5.22 so I can't isolate which
> package but I can consistently get the failure with the newest packges
> and it works fine with the downgraded packages.
>
> Running Arch Linux
> git 2.4.5
> perl 5.22.0
> perl-authen-sasl 2.16
> perl-mime-tools 5.505
> perl-net-smtp-ssl 1.03
>
> .gitconfig
> [sendemail]
>     smtpEncryption = tls
>     smtpServer = smtp.gmail.com
>     smtpUser = juston.h...@gmail.com
>     smtpServerPort = 587
>
> Regards
> Juston
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