I have intermittent problems sending an e-mail to a person using AOL but only her, no one else.
My cousin uses AOL. I will send her an e-mail and it will be returned telling me "permanent error". The next one I send might go through with no problem. They again, one will come back with the same message.
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Thunderbird obviously did it's job by handing the message to your providers SMTP server. The fact that it gets delivered sometimes indicates you have the settings in Thunderbird correct.
You could ask your provider why all your messages do not get delivered.
When I send the message in my ISP it goes with no problem.
I prefer using Thunderbird but for whatever reason it only goes sometimes and other times it is returned telling me "permanent error". Very frustrating. Until the past week I've had no problems with it.
Comparing sending by webmail and sending via SMTP server is meaningless.
Well not competely. It means you have this problem with your providers SMTP server.