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How can I send outgoing mail through my Email Security Gateway using my iPhone?

  • Type: Knowledgebase
  • Date changed: 10 months ago
Solution #00003338

Scope:
All Email Security Gateways in use with one or more iPhones, all firmware versions.

Answer:
In order to enable mobile devices like the iPhone to send mail out through the Email Security Gateway, you'll need an authentication server. Once that's been configured, you'll need to configure the Email Security Gateway to use it when authenticating outgoing mail from external devices.

-=Firmware version 4 and below
In order to enable mobile devices like the iPhone to send mail out through the Email Security Gateway, you'll need an authentication server. Once that's been configured, you'll need to configure the Email Security Gateway to use it when authenticating outgoing mail from external devices. To enable Outbound / Relay authentication on the Email Security Gateway, navigate to the Advanced > Outbound/Relay page, select the authentication server type (SMTP or LDAP), and configure the necessary options.

-=Firmware version 5+
In order to enable mobile devices like the iPhone to send mail out through the Email Security Gateway, you'll need an authentication server. Once that's been configured, you'll need to configure the Email Security Gateway to use it when authenticating outgoing mail from external devices. To enable Outbound / Relay authentication on the Email Security Gateway, navigate to the Basic > Outbound page, select the authentication server type (SMTP or LDAP), and configure the necessary options.

 
It's also important to make sure the traffic between the mobile device and the Email Security Gateway is not interrupted, so if you are using a Cisco Firewall, disable the SMTP fixup protocol (or enable the NO INSPECT ESMTP option) there. Then, go to the Advanced > SMTP/TLS page and enable TLS over SMTP (which the iPhone uses when communicating over SMTP). Lastly, you will need to change the outgoing SMTP port on the iPhone to 25 (by default, it might be set to 587), or forward incoming firewall connections on port 587 to the Email Security Gateway on port 25.

After making these changes, the iPhone should be able to relay outgoing messages through the Email Security Gateway (as long as it is able to authenticate with the authentication server).

Additional Notes:

When configuring a mail account on your iPhone, after setting up the authentication on the Email Security Gateway as above, you may need to explicitly specify the authentication method as Password. You can find this option on the iPhone under Advanced for that particular email account. Then, of course, you'll need to enter your password for that account into your iPhone.



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