I've looked around for a solution to this problem but all I see are similar complaints. I receive mail just fine but sending mail is strictly hit-or-miss and it is extremely aggravating.

Apple mail will not remember my passwords in any predictable way. I've tried some fixes suggested online but it always seems to revert to the same behavior. Apparently Apple is aware of this but neglects to fix it.

This isn't connected to any iPhone conflict or any other device or anything of that sort. In fact since I got an iPad I find it to be much more dependable for email. And the problem goes back to way before I got the iPad.

I'm really desperate to either fix it once and for all, or replace Apple Mail with another app, but I have no idea what's a good one, and which one will still be around for a few years. I read something about Thunderbird but it appears it's still in beta.

ANY suggestions would be appreciated.

Can you give us some detail as to what error codes you get? What shows up in Console at the moment that happens? Is it always from the same ISP?

I check and send from 6 different email accounts from 3 different servers (my website, my ISP, and my backup dial-up account email) and have never had that problem sending. As far as receiving though, two of the three on regular basis pop up asking for the password. I never re-enter because it never accepts it, I just cancel and it goes away after a while. It's a problem on the ISPs end with mail servers going down temporarily, which is what I suspect may be your problem in sending too, but without some detail it's hard to say where the problem is coming from.

Or, a system reboot will cure it, too.

I just sent a test email so I could document the steps of what happens. The problem is only with sending, as I said email can be received just fine. But in the current test, it asked for my password and when I put it in, the email sent just fine. The problem is that the behavior isn't consistent.

Briefly, when I try to send an email from my main account the spinner next to the mailbox name spins for awhile, then I get a window saying the message couldn't be sent from the selected server and asks me to select another server from a list.

So I use the server for a different account and it sends; the problem is the email address for that server *looks* like a sales address, which I would rather not use for strangers, and which can confuse my friends! So this isn't an optimal choice.

Just now, I went into the Mail prefs window and noticed that the server that works okay had "Use default ports" selected, and the problem server had "Use custom port" selected. On a hunch, I changed this.

I then went to send the test email, and after a wait, I got the screen saying the email couldn't be sent from that server and to select another; this is the step that happens constantly and gets annoying. However this time I re-selected the first server and re-sent. After another several seconds I then got the window asking for that account's password (which also always happens and which never works!) and this time the email actually got sent.

So it *might* be fixed, the problem is that the behavior is never consistent from one incident to the next. If I have further problems I'll stop back.

Thanks for your comments and suggestions.

Click the box that says - remember my password ? did you try that ?

Yep. I've tried a number of things. Sometimes they work for awhile.

It sounds to me like it's something server side, especially if it only happens to one server yet the other server sends okay. You're probably wasting time troubleshooting the OS. Have you checked their specs on settings to make sure your SMTP is set right? Maybe it needs SSL on or something, a specific port?

You're using a fairly recent version of the OS, Leopard or better?

That's not the way it works. The From: email address they see is what is set in Mail's main window under Account Type. It has nothing to do with the server it is going out from. The only place the server address shows up is in long headers.

When setting up SMTP servers it doesn't ask anywhere for an email address, just a user ID.

No, sorry for the confusion, it's the email address itself that looks like a sales address. I don't necessarily want that address showing up in the "from" line when I'm sending a comment or inquiry to a stranger. Looks like a sales pitch!

In other words, my email address is, e.g., joesmith@isp.com, which is the server that was acting up. then my only option is sending from joesmithorders@isp.com.

But it does appear that changing the "use port" setting has cleared up the problem.

Thanks for reporting back with the fix.

As an FYI as long as the smtp settings are right you can use any smtp server in combo with any email address.

joesmith@isp.com can be sent through isp#2.com for example.