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10.17. Sending Test Emails Fails

Exchange Servers

You may need to configure your Exchange server to support SMTP.  In some cases, Exchange will configure itself to be very restrictive with which IP addresses it will allow incoming SMTP connections to come from, and you will need to adjust that list to include the IP address of the PCs that the Assemblage Emailer tool will run from.

Important Note: Trumpet does not provide support for how to configure or manage Exchange servers - the information below is provided as an aid to you, but you should use it at your own risk.  If you are not a certified Exchange administrator, we encourage you to contract with someone who is.  Trumpet will be unable to answer technical questions about these procedures.

 

550 5.7.1 Unable to relay

This is an error reply from your SMTP mail server indicating that your mail server is not configured to allow you to send emails through it.  Typically, mail servers for an organization will be configured to allow mail from within the organization to be sent to other addresses within the organization, or to addresses external to the organization. It will also typically allow mail coming from an address external to an organization to be sent to addresses within the organization. What it will typically not allow is mail coming from an address external to the organization to be sent (relayed) to another address also external to the organization. The configuration of the mail server determines whether such relaying is allowed, and which addresses are considered internal vs. external. Often mail servers will require you to authenticate before they will relay messages. 

For Assemblage's emailer tool to work properly, your SMTP server must allow for mail to be sent from within the organization to be sent to other addresses external to the organization.  Your system administrator will be able to assist you in the configuration of your mail server to allow for appropriate relays.

 

Error sending text email - can't send command to SMTP host sun.security.validator.ValidatorException:  PKIX path building failed:  sun.security.provider.certpath.SunCertPathBuilderException:  unable to find valid certification path to requested target

If you are using a self-signed certificate for your Exchange server, you have two options:

Tell Assemblage to not check the certificate

  1. Go to Assemblage, Tools->Options, Email
  2. Change the Authentication Type to be 'SSL w/ Self Signed Cert'

Register your self signed certificate with the Java runtime on the workstations that run Assemblage

  1. Export your Exchange certificate in .p12(.pfx) using the Export-ExchangeCertificate command in the shell. You can get a list of certificates using Get-ExchangeCertificate.
  2. Use the following Java command to import the certificate:
        keytool -import -alias imap-server -file <path to exported certificate>
  3. It seems depending on the security set in Java, you may also need to add the issuer of the Exchange certificate as a trusted authority

Remember that Assemblage will use the latest 32 bit Java runtime installed on the workstation, so make sure you run keytool from the correct directory!

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