How to integrate an On-Premise Edge installation with strict SMTP servers  

Some SMTP servers have stricter requirements and/or different configurations than others. One example is Office365. This article will focus on Office365, but may be applicable to other SMTP hosts.

First, two links for later:

http://docs.apigee.com/private-cloud/latest/configuring-edge-smtp-server

http://docs.apigee.com/private-cloud/latest/how-configure-edge

If you have followed the article linked above to configure your SMTP server, but are getting the following error message, please read on:

[error] a.d.Dispatcher - Sending the email to the following server failed : smtp.office365.com:465
org.apache.commons.mail.EmailException: Sending the email to the following server failed : smtp.office365.com:465
...
Caused by: javax.mail.MessagingException: Could not connect to SMTP host: smtp.office365.com, port: 465
...
Caused by: javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?
... 

At first, you may be wondering why port 465 is showing up in logs above when you may have configured 587. If this were the only problem, a simple workaround would be to use iptables. For reference, the following iptables definitely works (but unfortunately doesn't help for this issue, as the port isn't the only problem):

sudo iptables -t nat -A OUTPUT -p tcp --dport 465 -j DNAT --to-destination :587 

(Note that even with that iptables rule, you will still see port 465 in the logs. The iptables rule technically works, but there's more to this than just the port).

After making the following changes (and removing iptables):

conf_apigee_mail.smtp.host="smtp.office365.com" 
conf_apigee_mail.smtp.port="587" 
conf_apigee_mail.smtp.channel="tls" 
conf_apigee_mail.smtp.tls="true" 

I was getting this error:

Sending the email to the following server failed : smtp.office365.com:587
org.apache.commons.mail.EmailException: Sending the email to the following server failed : smtp.office365.com:587
...
Caused by: com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM
... 

This final error can be solved by providing the full name and email address of the user sending the mail, for example (note the below must be EXACTLY right, and you can get this info from your SMTP provider):

conf_apigee_apigee.mgmt.mailfrom="First Last <email@outlook.com>" 

Note all the above configs are set in /opt/apigee/token/application/ui.properties per the "How to Configure Edge" link above. Also, after these are set, the UI must to be restarted using apigee-service. Also note that if you change your SMTP password, you must re-run the UI installer using your silent config file from initial installation.

I hope this helps. Thanks.