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We are building an email alert system which needs to send customized emails in real time based on certain criteria (think Google alerts). The application sends emails to multiple users from a web application currently implemented using a JMS bean that uses JavaMail to make the email sending asynchronous.

We were wondering if there are other utilities out there that might make this task a little more scalable and manageable.

On an related note, we have had major issues with Gmail (our mail server) while trying to send out bulk emails in this fashion (We sometimes send hundreds of alerts at a time). Managing our own mail server is an option, if that would help us scale this.