Apple Mail won't send invitations when initially closed

I just started using iCal to send invitations for appointments through Apple Mail. When Apple Mail is opened already when I create the appointment and click Send in iCal, it works fine. The mail is sent and delivered to the appropriate address.
But if Apple Mail is closed initially, the application starts and the invitation is queued up in the Outbox but is never sent. I can manually open up each invitation in Mail and send them individually, but why is the behavior different? Whether Mail is opened or closed when I send an invitation, it ought to deliver the invitation automatically. By not being sent, I may not realize the invitation hasn't been delivered, making the process very error-prone. Is there a way to guarantee the invitation actually gets sent without having to check the Outbox every time?
Is this an iCal bug or an Apple Mail bug? I saw no settings in Apple Mail for sending messages at shutdown or any other setting like this. Instead, these invitations may end up being buried in my Outbox for a very long time before I notice and by then, it may be too late.

ronright wrote:
Since I bought a new modem/router (Netgear n600), my Apple mail won't send e-mails. It will receive. My ISP is AT&T & the email accounts are via yahoo. I have a Macbook Pro with a recent OSX.
The most recent OS is currently OS 10.8.3. Your system profile confirms you are still using Mac OS X (10.7.5). If this is incorrect, please correct your profile so that you will get the correct troubleshooting suggestions/solutions.
Also, post in the OS/Mail forum of whichever OS is currently installed on your MBP. It's where the OS/Mail expert helpers hang out at.

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Apple Mail won't send invitations when initially closed

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