Mail POP outgoing emails not received (seemingly random) - Experts needed!

Please, please help...
I'm having a very strange, very frustrating problem that I believe comes down to the Mail application on my Mac. I am running Snow Leopard (10.6.4) and using three email accounts I access through Mail via POP, and have done so without a hitch for years.
Recently, friends and colleagues alerted me to the fact they have not been receiving emails I've sent. Emails that appear in my Sent box. It seems that some people have received ALL emails I've sent them, some people have received SOME but not ALL emails I've sent, and other people have received NONE of the emails I've sent them in the past couple of months (this I only discovered a few days ago, much to my dismay).
I can see no pattern to which emails have and have not been received. It appears to be occurring across the three separate accounts, and with different outgoing mail servers. This is what leads me to believe the problem lies with Mail, and not the servers themselves, though I may be wrong. I cannot tell which emails have not been received, and can no longer trust that emails I send will end up at their intended destination.
I cannot find any information on this kind of problem. Please help me. I'm desperate, and at a complete loss!!
P.S. I just sent some test emails to a friend using different combinations of my three email accounts and outgoing servers. Two of the emails were not received, each sent via different outgoing servers (and different accounts). However, all the emails appear in my Sent box.

Hello, and welcome to the Discussions.
This sort of random experience seems likely to be caused by the use of Rich Text Format. To test this, take a previously sent email that a friend did not receive, click on Message/Send Again, then click on Format/Make Plain Text, and then resend it. If they now receive, it is likely the RTF when it converts to a form of HTML is triggering a SPAM filter somewhere in the path to this recipient, and blocking the message.
Ernie

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Go to Solution.

GeezingInVA2 wrote:
I noticed my email account server settings don't match what is defined on the FiOS email setup page on verizon.com.
The server setting I have for my POP3 is "incoming.verizon.net" (not pop.verizon.net) and my SMTP server setting is "outgoing.verizon.net" (not smtp.verizon.net).
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For safety...
First Quit Mail, then I'd backup these two Mail folders, by right clicking on them in the Finder, then choose Archive/Compress.
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