I am no longer able to email to a group

I have been trying for 3 days to send e-mail messages to a group from the contacts I set up in my address book. I have been able to do this for years, and all of a sudden, it does not work. I always get the same message:
Sending the message content to the server failed.
Select a different outgoing mail server from the list below or click Try Later to leave the message in your Outbox until it can be sent.
I have tried sending the message with attachments, without attachents, to a smaller group size, etc. None of it seems to help. I was getting this same error message randomly for the past month or so, but I would just leave it be, go on the internet, then go back and re-send and it would work. Does anyone know how I can fix this? I have called my e-mail provider, and all my settings are correct. They think it's a problem with my Mac.
Thanks,
Julianne

First, if you can access the email account directly through webmail via your Safari Browser, try that first, so you get the message(s) out ASAP.
If it's an Apple iCloud account, go to www.icloud.com to sign in directly. With OS X 10.6.8, you can still use Mail through the browser, but the other functions of iCloud are not available.
After you've sent out your emails, then you can return to this page and attempt to resurrect Apple Mail...
Do you have multiple email providers linked through Apple Mail?
Is the option 'Use only this server' checked?
There are a couple of extra options and screens for configuring SMTP mail servers that may be hidden unless you know where to look for them.
Highlight the name of the Outgoing Mail Server to 'Edit SMTP Server List'
(Incoming Mail Server works the same way, but you're having a problem with Sending, not Receiving...)
This reveals Account Information and Advanced tabs with additional configuration options.
In some instances unchecking Use Secure Sockets Layer (SSL) makes it work again, but I'm not prepared to address the security concerns that arise without the use of SSL, so if you have any doubts, DON'T UNCHECK SSL. (What is SSL? http://www.digicert.com/ssl.htm)
(Some names and details intentionally obscured for privacy)

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Question
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