Outlook 2011/Gmail Account

[jstevens]

I am having a challenge where the recipient is informing me that they are not receiving certain e-mail messages from me. I'm not sure why as the e-mail header reflects the message(s) as being delivered. Is there an issue on the recipient's side?

Outlook 2011 is for Mac and I am using Gmail's outgoing server: smtp.gmail.com

Your comments are appreciated,
John

[StuartR]

Email is, unfortunately, not a guaranteed delivery mechanism. There are many places that a message could simply get lost with no notification to anybody. The most common cause of this is anti-SPAM software running at an ISP or on the server where the email arrives in the recipient's organization.