> On Jan 30, 2018, at 11:53 PM, Vladimir Hidalgo <vladimiro...@gmail.com> wrote: > > I'm using Postfix inside Google Cloud Compute Engine with outbound > port 25 blocked by default and I want to use Postfix to relay email > from my org. > > I've setup both SSL and TLS modes successfully (diff installations) > but the problem is that I generate an unique email for each of the > 1000 recipients and sending this causes a DoS alert on Gmail after > about 50 consecutive emails. > > Their support advice to reuse the connection to send more than 1 email > per connection, but as per the documentation TLS / 587 is not > supported for connection caching. > > What about SMTPS on port 465?. I've successfully configured Postfix by using:
Postfix does not support TLS connection re-use. The destination port plays no role in this, nor does use of wrapper-mode vs. STARTTLS. I'm afraid you'll need to find a nexthop relay that is willing to accept your mail traffic one message per connection. You can configure a TLS session cache (smtp_tls_session_cache_database) to reduce the cost of setting up TLS for each message. This may not appease the resource limits imposed by your current relay provider, but it won't hurt. -- Viktor.