Mac Mail Will No Longer Send

Mac Mail on os 10.4.11. Stopped sending reliably about 30 days ago. Have sat thru 3 one hour phone calls with SWBell/ATT tech support. All settings passwords and ports are correct (and have not changed for years). Mail sending often (but not always) pops up the password window. Have reset and reloaded keychain and basically disabled for now as this does not appear to be the root problem) Asks me for my password but won't take it about 98% of the time. Have also deleted and reset all my accounts in mac mail. Did not help. Workaround that do work are: Going online to my Yahoo mail account and sending myself an email seems to break loose the block and lets me send at least one outgoing email after I download the incoming mail to my mac mail. Sometimes going into preferences and choosing a different account setting, Saving. Going back in and choosing the intended and neccessary account setting, Saving. will let me send one or more emails. Sometimes just waiting a few minutes and trying to send again works. Seems to work more reliably at home where I am using Roadrunner SMTP than at office where using the SWBell/ATT smtp settings. All was working great until about July/Aug. We have several computers at my office, all same OS, all same email smtp protocol...all quit sending at same time. Only thing we did was update our firefox which should have nothing to do with Mac Mail. I know we are using an old OS but our store software needs to run on these older macs so must stay on Tiger....any big ideas out there?

Hi DGMMM, and a warm welcome to the forums!
One thing that can mess up Mail is a malformed eMail on the server, might have a look through Webmail to see if there's one about that time that isn't downloading & trash it.
Are these POP or IMAP accounts?
What SMTP port are you using with AT&T?
Are you getting this?
Mail: Can't send messages, "Cannot send message using the server smtp.xxxxx.com" alert appears...
http://support.apple.com/kb/TS1482

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Why? It's not your fault. It's because how Apple Mail stores mail, it simply is not robust enough.
A robust program assumes that it may crash at any moment while writing to any of its files, and that there will be undiscovered, rarely occurring bugs that will have similar effect. The damage it does needs to be detected later and then repaired automatically or degraded gracefully so only one mail is lost, and not all of them.
Evidently, Apple fails to do so or didn't do a thorough job.
For mail this is really urgent, because a mail program does many things simultaneously which increases the chance that things go wrong once in a while, and on top email comes from the wild world outside and can contain many types of junk that need to be contained. Mail server delivery data muck, deliberate attempts to hack your mailbox by mail, phishing attempts, html newsletters made by Neanderthalers or marketeers, other buggy mail programs, poorly made phising mails, regular spam, you name it.
So there are a lot of possible 'runaway cars' that may dent another in the parking lot, but this should never cause an entire parking lot building to tilt so all the cars roll to one side of the floor and while still there, can't open the doors anymore.
Computer science made many solutions for this the past 3 decades and it isn't even that hard to do, many file formats have auto-recovery features.
For example: You may have seen a movie on TV or internet, or skype conversation that goes into "weird blocks" a few seconds and then go back to normal. That's damaged data and auto-recovery of the data format kicking in to fix it or at least reduce the damage. Without it, you'd be looking at digital snow for the rest of the show. Apple does the latter to your mail.
In modern databases this is done all the time, because a company can't afford to lose all of its financial data because 1 record went bad or there once was a power outage. For a user, losing his/her mail can be just as catastrophic. If they can, Apple can. Come on.
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Mac Mail Will No Longer Send

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