Re: Has gmail SMTP authentication changed recently?

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Once upon a time, Frank Bures <buresf@xxxxxxxxx> said:
> More info:
> 
> openssl s_client -connect smtp.gmail.com:587 -6

That is incorrect.  Port 587 will require SMTP+STARTTLS, not SSL-wrapped
SMTP (which is port 465).  You'd want to add "-starttls smtp" to your
openssl test command.  However...

> returns:
> 
> C0A22B281F7F0000:error:80000065:system library:BIO_connect:Network
> is unreachable:crypto/bio/bio_sock2.c:178:calling connect()
> C0A22B281F7F0000:error:10000067:BIO routines:BIO_connect:connect
> error:crypto/bio/bio_sock2.c:180:
> connect:errno=101

STARTTLS vs. SSL-wrapped is not going to cause a network unreachable
issue.  You should probably check your Internet path with mtr, like:

$ mtr --tcp -P 587 -6 smtp.gmail.com

(and see how -4 looks as well).  It's normal to have hops along the way
just be "waiting for reply", and also to see some packet loss (as the
"probe" packets used by mtr can be rate-limited), but it should still
end with a hop at Google (for me, it's a host with reverse DNS in
1e100.net, which is part of Google's infrastructure).

It's possible that one protocol is taking a route through Cogent, who
thinks highly of themselves and refuses to peer on IPv6 with some other
networks (like Google and Hurricane Electric).

-- 
Chris Adams <linux@xxxxxxxxxxx>
-- 
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