'Send email alert' assertion fails when using Office365 as the SMTP server

Document ID:  TEC1840025
Last Modified Date:  07/10/2017
{{active ? 'Hide' : 'Show'}} Technical Document Details


  • CA API Management Gateway


  • CA API Management Gateway:Release:9.0.00
  • CA API Management Gateway:Release:9.1.00



When attempting to use the 'Send email alert' assertion with Office365 you may encounter the below error


530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM


When the Gateway completes a SSL handshake with the SMTP server the Gateway almost immediately generates an additional ClientHello (starts a renegotiation handshake) and SMTP server returns a TCP RST.



To prevent this add the com.l7tech.server.policy.emailalert.useDefaultSsl system property to bypasses the additional renegotiation.


1. Connect to the Gateway and edit: /opt/SecureSpan/Gateway/node/default/etc/conf/system.properties

2. Add this property com.l7tech.server.policy.emailalert.useDefaultSsl=TRUE

3. Save the file and restart the gateway.

4. It is assumed that office365 root certificate is added to the gateway( Policy manager-> Manage Certificates)

5. In Email alert properties select protocol as “SMTP with STARTTLS” port 25/587.

6. Select Server Required Authentication checkbox.

7. Domain name must be provided for all user names and emails ids(Ex: xyz@ca.com).

8. Adding proper email ids it should send email normally.

Please help us improve!

Will this information enable you to resolve your issue?

Please tell us what we can do better.

{{feedbackText.length ? feedbackText.length : '0'}}/255


Not what you were looking for?

Search Again >

Product Information

Support by Product >


Join a Community >

Chat with CA

Just give us some brief information and we'll connect you to the right CA ExpertCA sales representative.

Our hours of availability are 8AM - 5PM CST.

All Fields Required


We're matching your request.

Unfortunately, we can't connect you to an agent. If you are not automatically redirected please click here.

  • {{message.agentProfile.name}} will be helping you today.

    View Profile

  • Transfered to {{message.agentProfile.name}}

    {{message.agentProfile.name}} joined the conversation

    {{message.agentProfile.name}} left the conversation

  • Your chat with {{$storage.chatSession.messages[$index - 1].agentProfile.name}} has ended.
    Thank you for your interest in CA.

    Rate Your Chat Experience.


agent is typing