On Wed, Mar 25, 2015 at 12:56 AM, Andrew Kay <[email protected]> wrote:
> Until a few years ago, I imported all mail via POP3. This stopped when
> Google decided that self-signed certificates were less secure than no
> encryption at all (how does this make sense?). At that time, Google
> employees advised users either to get an SSL certificate signed by a trusted
> CA, or have email forwarded from the external server.

Connecting in the clear to a POP3 server is your risk but why should
Google allow encrypted connections to hosts with a self-signed
certificate? As you say, this is a family member providing you with an
email account, no doubt associated with a domain you own, for free.
That is directly competing with what Google sells.

> So for the last few years, I've had my email forwarded from there with no
> problem. Then tonight I am told by my close family member that my emails
> will no longer be forwarded, because Gmail is rate-limiting all mail sent by
> that server, because some of the emails I get forwarded are spam. To make
> matters worse, Gmail is apparently doing this in at least one instance by
> silently dropping messages while still indicating that the mail has been
> accepted.

If I were Google I would ask the question "why should I accept emails
from an MX host that is forwarding them on when so many of them
contain Spam? Why is that host not filtering out the Spam?".
I too have my own VPS and forward email for some of my domains from
there and I have never (yet) been rate-limited or had messages not
arrive. I do maintain the virus scanner and Spam filter and it's a
fair amount of work.

> So as far as I can tell, Google's official policy is:
>
> Sending passwords in cleartext is better than trusting a certificate signed
> by your close family member, because at least you know that cleartext is
> insecure.
> If you want to not do that, then you must either convince the server admin
> to buy an SSL certificate so that you can read your email more conveniently,
> or
> Convince the server admin to forward all your email along, risking their
> server's reputation and potentially interrupting normal use of their service
> by other users

Again, Google is in the business of selling Apps for Business. You are
effectively trying to bypass the email part and still use free Gmail
to send/receive email for your domain.

If your family member is providing email as a service to others, then
he really should be using a proper certificate.

> The obvious solution would just be to let me approve a particular
> self-signed certificate. I am not the first person to ask for this option.
> But in any case, following Google's advice to have email forwarded along
> should certainly not result in mail being silently dropped, let alone other
> people's mail...

The obvious solution for you yes, but not for Google. They are
protecting themselves from every Joe out there forwarding mail from
their VPS without adequate spam/virus protection, and protecting their
business model. I'm sure it's only a matter of time until they stop
all unencrypted connections too.


-- 
Marko

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