Inbound email: telnet works but Gmail doesn't

[pasty]

I'm setting up an Alfresco AWS instance and trying to configure inbound email.

As per the inbound email documentation I've configured it, hosted the Alfresco mail server on port 1025, set up an iptable rule to forward port 25 --> 1025, set up an folder in Alfresco with the alias 'dropoff' and added my work email as an allowed user for sending emails. I've also ensured all the email ports (25,1025,465,etc.) are open on the EC2 instance

So far so good. If I test everything from my local computer with telnet:

helo mywork.com mail from:myname@mywork.com rcpt to:dropoff@alfresco.mywork.com data From: adinihan@mywork.com Subject: test mail from command line  this is test number 1 sent from linux box .

Then it works. I look in the Alfresco folder and there's the test email document. However, if I use Gmail and sign into myname@mywork.com and send an email through Gmail, then it doesn't work. It sends with no errors and there's nothing in Alfresco logging, however the document just never appears in the Alfresco folder. The from/to address is the same as the telnet command's one.

Since I can telnet from my local computer to the instance I assume it's not an issue with ports on the EC2 instance. Why would telnet work but sending it via Gmail not?

[pasty]

Just received an automated email via Google with this error message:

TLS Negotiation failed: generic::failed_precondition: starttls error (0): protocol error

So I'm guessing that's what seems to be causing the issues

[mehe]

If you have to use Tls as encryption you need to enable it in alfresco-global.properties

email.server.hideTLS=false
email.server.enableTLS=true
email.server.requireTLS=false

You should also turn on logging for org.subethamail in log4j.properties and would have to enable ssl for Java.

There is an „obsolete“ documentation page, that has some helpful information and links:

Inbound SMTP Email Server Configuration 

you can also try to hide tls and disable it on the alfresco side - But I don‘t know if Google Mail will accept this... also it‘s Not recommended.

Have you looked into AWS documentation for TLS endpoints and TLS wrappers Connecting to the Amazon SES SMTP Endpoint - Amazon Simple Email Service  ?

STARTTLS encrypted smtp want‘s to Connected over Port 587 (Ort different potnumber), Not p 25...

[pasty]

I enabled TLS and got a log error saying the IMAP subsystem wasn't enabled when sending an email. So I also added the IMAP config to the alfresco-global.properties and now again there's no errors on sending but the email never makes it.

[mehe]

I was off for a few weeks - still having the problem?

[pasty]

Yes still having it. When I send an email I just get the same "TLS Negotiation failed" message back after a short delay from Gmail that I mentioned above. I was thinking it might be a difference in TLS version, like maybe Alfresco was using v1.0 but Gmail uses v1.2. But I can't find any configuration options for changing the TLS version Alfresco uses.