Both GMail and Hotmail use aggressive anti-spam heuristics and the MyAssistant tasks which send to many recipeints may be mistaken for spam.

Here area couple of links that may help:

Gmail:  support.google.com/.../69585

HotMail (Live.com): mail.live.com/.../troubleshooting.aspx

If you have a specific message/number in the "bounce back" email, that may lead to the root reason for rejection. If you need additional help, please contact support. Regards.

Thanks Kyle.  We weren't receiving bounce back emails and the funniest part was that a single email to hotmail and gmail would go through.  We tried all of the solutions you suggested and in the end broke the task down into smaller tasks (i.e. one sent to employees with last names from A through C, another D through F, etc).  Since the number of emails going out on each scheduled task were smaller, hotmail and gmail are letting them through.

Thanks Kyle.  We weren't receiving bounce back emails and the funniest part was that a single email to hotmail and gmail would go through.  We tried all of the solutions you suggested and in the end broke the task down into smaller tasks (i.e. one sent to employees with last names from A through C, another D through F, etc).  Since the number of emails going out on each scheduled task were smaller, hotmail and gmail are letting them through.

Thank you for letting us know how you've resolved this issue.  I have incorporated your solution into article# 45681 in our Sage Knowledgebase.