Odd trouble with Apple Mail

Various Mac users in the extended family. Have been for years (since the late 80s for me).

So I've a lot of experience with nearly every version of OS Apple has ever produced.

My mom bought a new Macbook in the summer. Her old machine was getting flaky, it was like 10 years old, so not a huge surprise.

Her old OS was 10.4, new OS is 10.11 (El Cap).

She's using Apple Mail. I have occasionally used that in the past, but only on my Powerbook laptop, and even then only on vacation, where email need was limited at best.

Mom's email flakes out regularly, refusing to send to the SMTP server. So I have gotten a lot of "tech support calls" from her about this, and I haven't really been able to solve it. Have spent time on the phone with her ISP, and with Apple, trying to figure this out.

IT SHOULD NOT TAKE AN ADVANCED DEGREE(TM) TO FIX THIS.

Except that apparently it does. Pay attention to get yours.

So here's what is going on (Apple guy didn't know this stuff, ISP guy hinted at it):

Apple Mail ("AM") auto-configures an account for you based on an email address you give it when you first start it up, and you can add more later that will also auto-configure. OK, that's friendly, you don't have to be an expert on setup to get going on your brand-new machine.

AM now knows how to handle additional mail flavors, so you can do IMAP as well as POP. These two things aren't the same however, so it's interesting that it auto-configures for you. SMTP has gotten fancier over the years with security settings, and that's where the problem starts.

The long-term problem is that it continues to try to auto-configure for you--any time there's a glitch between your machine and the server, it attempts to re-auto-configure the entire account. This is a thing that AM didn't used to do, so it took me a long time to figure it out.

Well, the odds of that working right are probably slim. Fortunately, it looks like you can turn this off, which is probably the right thing to do immediately. There's a check-box on your account settings about "auto-configure" that you really want un-checked.

The problem mom was experiencing is that the auto-configure was going from port 587/password/SSL to port 25/MD5/SSL, and the ISP just doesn't do that. And AM wouldn't let go of it most of the time. The ISP does not change it settings. Not ever. Yours doesn't either.

And this "re-auto-configure" would take place any time there was any kind of comm hiccup between AM and ISP/SMTP server. This was, I believe, the real problem. Mom's ISP is just not able to keep up with its workload, then there are comm-channel hiccups, if you try to send email during one of those hiccups it tries to reconfigure the comm scheme by choosing some other settings, that fails because the ISP only uses the one group of settings

It seems like sometimes it would recover ok (like the settings got changed back ?!), outgoing mail would finally transmit, and then later there'd be another hiccup, outgoing mail wouldn't go out, and this would last for hours or even days.

So what you need to do is turn off the auto-configure-settings on your email accounts. Once you have the right settings, don't let AM change them again.

A few weeks after that discovery I found the help web-page on the ISP's own site that explained this whole things with pictures and red circles over the naughty check-box.

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What's also interesting here is that I still have an account with that same ISP, for a few more months. I don't use AM, I use SeaMonkey (altho not for much longer, as it's degraded, because it's a Mozilla product, (see other blog on that topic)). SeaMonkey is a whole different program, doesn't do this auto-configure at all. And I'm not using the same program settings anyway--I use the POP service, weaker security, etc., and virtually never have trouble at all--certainly nothing like what mom has had.

So I've convinced myself that it's this auto-configure that starts with what WAS once good settings, and gets stupid about them, and doesn't recover.

So turn that off. Bad dog.