SMTP not working for Mail. Works on iphone and smartermail.

Curious issue and some are suggesting that the issue might be with Mail.

One of the things I have always adopted when performing software updates is to always download the update from the Apple Downloads site rather than allow software update to do the update. Prior to implementing any of the updates I always perform a permissions repair and then a backup. After applying the updates I then perform another permissions repair and then another backup.

I have never had any problems with any software on either my MacBook Pro 17 or the iMac belonging to my Sister.

I dare say many would argue that the Software Update process should work faultlessly but that has not been my experience and the process I have adopted has resulted in faultless operation for a number of years.

The point I am making is that it could possibly be a permissions issue which may be resolved by performing a permissions repair to ensure that user ownership issues are not at play here.

Incidentally my Macbook Pro is configured so that POP email accounts use the default ports. Additionally, no matter where I happen to be and whoever's ISP ADSL link I happen to be using I have never had an issue receiving mail or sending mail so long as I choose/configure the right outgoing smtp server which is simple enough to create.

Perhaps I am completely off the mark here too but the comments are offered in order to help.

Chris

Thanks 2point5 for your remarks. Helpful indeed.

Well, I've had these problems for the past few weeks myself. I know it has nothing to do with permission problems for me. Also was happening 10.6.6 and 10.6.7.

It seems on occasion that Mail has a problem connecting with the outgoing server. If you have it on the default port settings for the outgoing server, it takes a longer time for mail to come back and tell you it can't connect to the server. If you put your port number in the custom port instead of default, it comes back almost immediately to let you know that it can't connect. Makes a big difference from watching the process go on and on for minutes or to the point of locking up to only seconds now to get a failure message. For me, when it happens now, it only takes seconds to give me the failure and usually on the 3rd try it goes through and is fine after that.
Is this a connection issue with isp? I don't know, but it's definitely an issue with authentication to the isp through the outgoing smtp port.

What I did find this morning when checking my Keychain was that I had 3 different passwords saved for the POP incoming and 3 different passwords for SMTP outgoing for the same account in Mail. I deleted all of them and restarted Mail. I had to re input the passwords to receive and send mail, but now my keychain only has one password for Mail to send and receive on that account. I'm thinking that this may have been a part or maybe all of the issue.
I won't say for sure just yet, but sending mail now is much quicker with no delay at all. I can't duplicate the issue by restarting the computer or quitting and restarting Mail now.
So, hopefully the issue won't occur again.

Message was edited by: Glenn Leblanc

I, too, have been having similar issues. Both on my iMac and MBP. While I have not completely investigated the MBP, I have done everything to address this with the iMac. I have AT&T DSL (which is challenging enough) and have gone through their email address validation process they require when using email addresses other than theirs. What I have is a MobileMe email and an email with my own domain. However, as stated above, I have to use AT&T's SMTP server. I have tested that this server is indeed working since I have sent emails from two iPhones on my network while in airplane mode. I have also successfully tested these emails using Thunderbird on my iMac. Hence, it must be Mac Mail.

So I have repaired permissions, keychains, connection doctor and finally deleted all email accounts and associated keychains. I even deleted the SMTP server listings that were set up by iPhoto and Aperture. I did notice a conflict in the SMTP server these two apps set up (smtp.me.com). Unfortunately, none of those attempts worked.

What has been working for the last few days is letting Mac Mail set up my MobileMe email the way it automatically wants to: as an IMAP account using all their default settings (including smtp.me.com). Historically, I have set MobileMe email to a POP account and not IMAP. I know that Apple prefers IMAP, but will allow POP. One has to contact Apple to get the account info. I never called, and surfed around to find the POP account. It was working ever since they changed from dot mac to MobileMe. What I have recently noticed is that Mac Mail automatically sets this up for you when you are setting up your first email account in Mac Mail. I would override this (no easy feat) using POP and AT&T's SMTP server. Out of frustration one day I simply decided to let it just do what it wanted to do, and set up my other email (i.e., the one with my personal domain) to it's same POP settings using AT&T's SMTP server.

Well, for whatever reason this seems to be working for the last 3-4 days. I don't know if this is the solution or if I'm simply sneaking email past AT&T's gates using smtp.me.com instead of theirs for sending email. But maybe it's an issue that Mac Mail just gets hung up on MobileMe set to a POP server. Don't know why that would affect the SMTP server. But maybe there is some connection between POP and SMTP. Maybe if Mac Mail can't get a POP connection, it causes issues elsewhere (e.g., SMTP). But then again, maybe had I contacted Apple for MobileMe POP, there is some other thing they do on their end beyond giving me the POP account setting.

Fingers crossed...

I don't have any other devices or use any other servers such as Mobile Me, so my setup is simple. Only one POP Account through AT&T.

Never have problem receiving Mail, just sending on occasion. This started several weeks back and only happens on few occasions. A few days back it locked up in the process and I couldn't get it to send at all. That's when I discovered that I couldn't change the custom port to 465 and make it stay. Something got corrupted and would not let it access that port at all. After resolving that issue, I knew it was a port problem and decided to leave it custom 465 rather than default. If 465 wasn't available, it was searching other ports and causing a longer delay.

Could have been my multiple passwords in Keychain cause a problem, but not sure yet. So far, so good.

I have seen that the majority of complaints have been with AT&T service. Maybe they are occasionally having problems. I also know that they are making some changes to their services, but I don't know if it is causing issues.

Eventually, we'll get to the root of the problem.

I just got my iMac a few days ago. When I tried to set up Mail, I kept getting this message "The server SMTP rejected the password". How do I get around this?
Thanks

Sounds like your using the wrong password or don't have your setting right.

You should start your own help request so others can help you.

Joodles wrote:
We are having the exact problem with our smtp outgoing mail too for the last couple of days. Each and every time we attempt to send outgoing mail, we get an error that the server is not available. IF we select "try again later," sometimes we will discover that the email doe sin fact get sent...eventually...but not always.

Me too. AT&T DSL and Apple Mail. Problems began about a week or ten days ago. AT&T told me to change smtp server settings from smtpauth.sbcglobal.net to smtp.att.yahoo.com and to turn SSL on. No help.

The troubles may have begun immediately after I upgraded from 10.6.6 to 10.6.7 on my machine at the office, but I'm not certain.

Sometimes I can send email, sometimes I can't. I actually have two AT&T DSL accounts, one at home, one at the office, so I have my choice of two smtp accounts at either location. Sometimes one works, the other doesn't. I can't see a pattern. Sometimes smtpauth.sbcglobal.net works and smtp.att.yahoo.com doesn't, or vice-versa. As I recall, I am never able to send email with SSL turned on, in any account.

I haven't taken careful notes, I'm going on memory, and outgoing mail seems to work inconsistently, so this information might not be completely reliable.

Connection Doctor gives inconsistent results. If the "status" dot for an smtp server is red, I definitely can't send. If it is green, sometimes I can send, sometimes not. The connection status of smtp servers seems to vary unpredictably from one hour to the next. Sometimes Mail will try to send for a long time with the little gray cursor spinning. Other times I get Mail's "try another smtp server" or "try later" dialog box immediately. Sometimes, if I let the cursor spin long enough, the message eventually gets sent.

I seem to be able to fall back on smtp.gmail.com, because I have a gmail account. I don't really understand the implications of using gmail's smtp server. It seems to work - that's all I know. Setting up a Gmail account might be a solution for some AT&T users who are completely unable to send email via AT&T.

Interestingly, using the same smtp servers from home (I live a city or two away from the office, in the same region), I have no trouble sending mail. This may be because I use a different machine at home, a MacBook. That's still on OS 10.6.6, come to think of it. In addition, the DSL modem at home is in bridge mode. I enter the AT&T settings in my WiFi router. My DSL modem at the office -- the problem location -- is not in bridge mode. This might be relevant, or might not be.

I have another theory about the trouble.

Having struggled with these issues for many hours, often scrutinizing Connection Doctor in Mail, I'm starting to get the impression that some AT&T smtp server addresses are aliases for others. If my list of smtp servers includes two smtp addresses that might resolve to the same smtp address somewhere in AT&T Land, the status dot on one or both seems to turn red in Connection Doctor. Removing one of them from my list of SMTP servers seems to turn the status light to green for the other one. I'm not sure how consistent this has been.

Duplicate SMTP servers could be a problem because, over the years, AT&T has suggested quite a variety of SMTP servers and configurations, which I have not always deleted from my list of SMTP servers. This might apply to others.

On the other hand, duplicate SMTP servers (or aliases) is probably not the whole problem, because I have cleaned up the list of smtp servers at the office. For awhile, that seemed to help. But, now I again have problems.

I've talked to tech support at AT&T three or four times. They are out of ideas. Frustratingly, AT&T keeps no logs of attempts to send email. The tech says the log on my modem would contain no useful information. The tech says it's the fault of Apple Mail. He says he has "heard of" other similar problems with Apple Mail. On the other hand, the tech says AT&T keeps no database of recent connection problems, so he's only listening to the buzz and guessing.

I will continue to investigate. I'll try the 10.6.6 MacBook at the office and report back.


Cheers, Tim

Timothy Miller wrote:
The troubles may have begun immediately after I upgraded from 10.6.6 to 10.6.7 on my machine at the office, but I'm not certain.

It's me, replying to myself.

I brought the MacBook to the office. The office computer has Mail v 4.5 and OS 10.6.7. The MacBook has Mail v 4.4 and OS 10.6.6.

I seem to be having similar problems sending mail with both machines. So, maybe it isn't the OS upgrade.

I have cleaned up the list of smtp servers on both machines. The problems remain.

Tim

I have solved my outgoing email problems with AT&T dsl. I got no help from AT&T level 2 tech support. Googling around did the trick.

The basic problem is that AT&T is notoriously user-hostile to email users, especially those who want to send email by smtp. The web is crawling with complaints about them. They change the requirements for smtp server settings without notifying their customers.

Several commentators have suggested getting a gmail account and using Gmail's smtp server.

I'm going to start a new thread to explain what went wrong, why, and how to fix it. As far as I know, this solution will likely work for other frustrated users.

I'll call the new thread "AT&T smtp problems solved"

Tim

Timothy

I've read your post on how to fix the problem.
The changes AT&T made to their email servers were sent out over 2 years ago. At least for the BellSouth customers. Perhaps you missed the email or dismissed it as spam.
I've made those changes a long time ago to the server settings and port settings. I also have the webmail setup as you described. That was part of the process when they went with the Yahoo server. If you hadn't made the changes in the past, I don't really know how you got away with being able to send mail at all. But I'm speaking as a former BellSouth customer.

Anyway, that doesn't solve the problem most are having with intermittent problems. It probably solved your problem of not sending at all, but you'll still probably have the same intermittent problems everyone is reporting. Hope not for your sake.
Try using the Connection Doctor in Mail from time to time and see if you get failures. That will be the easiest way to tell. At certain times, the connection will fail after repeated attempts on checking.

Getting a Gmail account will solve the problem. But what happens when a problem starts with Gmail? Look for another I guess.

I have heard recently that AT&T is going to give an option of whether or not you want an email address with them. I suppose they will charge in the future if you do. So, maybe they are making changes and it's causing problems, but no way I can verify that.

I still would really like to see what the solution will be if anyone ever finds it.
Glad to see that you can at least send mail again.

Glenn Leblanc wrote:
I've read your post on how to fix the problem.
The changes AT&T made to their email servers were sent out over 2 years ago. At least for the BellSouth customers. Perhaps you missed the email or dismissed it as spam.

Hi Glenn,

You're partly right. AT&T did announce some of those changes about two years ago. But they haven't been consistently disabling non-compliant email use until recently, as far as I can tell. Meanwhile, I was never notified. This is not the first time AT&T has changed requirements for email settings without notifying its users properly. If you Google it you will find hundreds, perhaps thousands of complaints about it. You will also find some AT&T users who say they were notified by email.

I've made those changes a long time ago to the server settings and port settings. I also have the webmail setup as you described. That was part of the process when they went with the Yahoo server. If you hadn't made the changes in the past, I don't really know how you got away with being able to send mail at all. But I'm speaking as a former BellSouth customer.

That's part of the problem. If they announce technical changes two years ago, don't enforce them, and then start enforcing them without notification, there's going to be trouble. As you can tell by the tone of my message, I'm deeply annoyed.

Anyway, that doesn't solve the problem most are having with intermittent problems. It probably solved your problem of not sending at all, but you'll still probably have the same intermittent problems everyone is reporting. Hope not for your sake.

Well, thanks. I'll also feel stupid. When I posted this, I was pretty sure I had found the answer for self and possibly many others. Maybe not. Still, I hope my suggestions will help some users.

Try using the Connection Doctor in Mail from time to time and see if you get failures. That will be the easiest way to tell. At certain times, the connection will fail after repeated attempts on checking.

I've posted on other threads recently, comparing notes with others trying to isolate the problems. I've been looking at the Connection Doctor quite a lot. When the status dot for the smtp server is red, the email will definitely not get sent. When it's green, sometimes it gets sent, sometimes it doesn't. The status dots have seemed inconsistent at times. Sometimes if you "check again" status dots will change from red to green or vice versa, even though you haven't changed any configurations. That doesn't make much sense.

Getting a Gmail account will solve the problem. But what happens when a problem starts with Gmail? Look for another I guess.

Yeh. I thought of that, too. That's why it seemed important to get the AT&T smtp working right.

What's your best guess about the cause of these problems? Are you having them, too? When did they begin?

Best regards,

Tim

I also am unable to send any email, EXCEPT via my .mac account. But I get no error messages. The outgoing mail just stays in the outbox indefinitely.

I am able to send fine from webmail, btw.

Is this a different problem from what other people are describing?

I tried a permissions repair. Alas, it did not fix the problem. I still can't send any mail.

What's your best guess about the cause of these problems? Are you having them, too? When did they begin?

I noticed it about 6 weeks ago. But since I'm not a big email sender, I can't say when it actually began.
I didn't really worry about the occasional glitch until I couldn't send anything at all. That was because something got corrupted and Mail couldn't access port 465. I got that fixed and continued looking at this intermittent problem since. I also cleared my duplicated passwords in Keychain for Mail. I had to do the same for my wife's computer. I found out she was also having an occasional problem.
But, some have an occasional problem and some are much more serious problems.

If AT&T is just getting around to taking out the old servers, it's something I'm not aware of. When I searched the web for problems, most of the posts and articles were written back in 2008. This was the time when AT&T went to the Yahoo servers.

For anyone not realizing what the settings are:
Incoming Mail Server: pop.att.yahoo.com > port 995 > use SSL > Authentication: Password
Outgoing Mail Server: smtp.att.yahoo.com > port 465 (don't use default) > use SSL > Authentication Password
User ID: use your full original email address
Password: whatever you've set with at&t

If you're with AT&T, you also have a yahoo account. You should go to http://att.my.yahoo.com/ and sign in (your orininal full email address and password). You can click on your name and edit your yahoo account info & profile. This is where all your email info is stored for AT&T web account.
You should check the web account through there also. Spam filter settings there do affect what you receive in your Mail application. If a message is moved from the inbox there, it will remove it from the server and you won't be able to download it to your local account. If you're not getting emails that you know you should with your AT&T address, then check the SPAM mailbox there.

My best guess none. I give up. It's very hard to pinpoint where the problem lies. Although most say it's with AT&T server, I've seen a few posts indicating that it happens with other servers other than AT&T. Your issue may be a bit different than most of the others posting. I'm not sure, but it seems there may be separate issues going on here.