Rebecca,

I cheated and used smtpServer = relay.apple.com and smtpEncryption = tls. Seems 
relay.apple.com does not require authentication and it just worked. 

I used an internal git mailing list to figure all this out, but seems the easy 
button was an smtpServer setup to be easy to use with git sendmail. It might be 
worth while to have folks reach out inside their companies to see if there are 
existing known good recipes?

Thanks,

Andrew Fish


> On May 27, 2020, at 3:07 PM, Rebecca Cran <rebe...@bsdio.com> wrote:
> 
> On 5/27/2020 6:12 AM, Laszlo Ersek wrote:
> 
>> So, it could be a MINGW64 packaging bug, perhaps.
> 
> I'm getting the same error, but with a different packaging of Git: mine's in 
> C:\Program Files\Git\cmd\git.exe .
> 
> It's version "git version 2.26.2.windows.1".
> 
> Of course it's possible it's just the same MINGW version that's been put into 
> its own installer.
> 
> 
> I also tried using my openSUSE WSL installation, but it failed with:
> 
> STARTTLS failed! SSL connect attempt failed error:1416F086:SSL 
> routines:tls_process_server_certificate:certificate verify failed at 
> /usr/lib/git/git-send-email line 1548.
> 
> 
> So I ended up copying it to one of my FreeBSD systems and sent it from there.
> 
> 
> -- 
> Rebecca Cran
> 
> 
> 
> 
> 


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