Long-standing problem sending from Mail; will reinstalling help?

I have been having difficulty sending mail from Mail for quite a while. I have posted to these forums about the problem, spent a good deal of time on more than one occasion with my ISP, paid for a pay-per-incident technical support session, paid an IT consultant to diagnose the problem, and had a consultation at the Genius Bar of the local Apple Store.


The problem persists. Periodically, sending hangs up. I have learned how to get around the problem. When I get the message that the outgoing server could not be contacted, I select edit SMPT server list, and change the outgoing server to "None." The mail goes out immediately. The next time sending hangs up I switch the outgoing server back to my ISP's SMPT server and the mail goes out immediately.


Recently I have tried two other email clients, Postbox and Mailsmith. Neither has ever hung up on sending. Both have their attractive features. One does not allow reorganization of mailboxes, only creating, renaming, and deleting. I am having difficulty importing some of my mailboxes into the other, and am having difficulty getting technical assistance with the problem.I am perfectly happy with Mail the difficulty I am experiencing aside.


Is it possible that reinstalling Mail will solve the problem? If so, how do I go about it? In particular, are there any precautionary steps I should take in doing so?

Macbook, Mac OS X (10.6.7), 2.4 GHz, 2 GB SDRAM, 233 GB HD

Posted on May 14, 2011 11:20 AM

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45 replies

May 14, 2011 11:45 AM in response to EricWeir

Is it possible that reinstalling Mail will solve the problem?


The only way to find out is to try it.


If so, how do I go about it?


Insert your 10.6 installation DVD. Restart. Hold down the C key until the Apple logo appears. Run the Installer. Restart. Run Software Update and apply all available updates.


In particular, are there any precautionary steps I should take in doing so?


Back up all data first.

May 14, 2011 12:21 PM in response to Linc Davis

On two tries the installer failed to open. It, too, hung up -- at the language selection stage. Finally, I booted the system, ejected the disk, reinserted it, and the installer ran. I was unclear about what I was to do in this case and aborted.


Do I have to reinstall the entire operating system just to ge Mail reinstalled or can I install it separately?


Thanks,

May 14, 2011 5:34 PM in response to creative soul

I've reinstalled OS X (Snow Leopard). It will take a while to determine whether Mail is behaving after the install. I sure hope so. Mail is not perfect, but I have not found another email client that I like as well.


That said, having struggled with this in the ways I've described over a period of at least several months and maybe a year, my sense is that something is wrong with OS X/Mail in this regard. If you Google this problem you will find that many people have had it. You will not, however -- if my experience is any guide -- find a solution.


I sure hope this one works. If it does not, I can only hope the next update of OS X, which I understand is due out in a couple months, will have fixed the problem.


I'll report back when I know whether the problem has been eliminated or not.

May 14, 2011 5:50 PM in response to creative soul

Anyone know how to fix this?


You're asking a different question than the OP. His question was how to reinstall Mail, and it's been answered. I suggest you start a new topic to address your question, but briefly, I think one of the most common causes of problems with Mail is that people install third-party add-ons, or hacks as I call them, to modify its operation. The hacks may seem to work for a while, but eventually a system update makes them incompatible. The user forgets about them, doesn't update them, and doesn't associate them with his problem. That's why I advise anyone who has inexplicable problems using Mail to test it in safe mode. If that doesn't answer your question, please start a new topic.

May 14, 2011 6:06 PM in response to Linc Davis

Linc,


Sorry no third-party add-ons or hacks have been added to my computer. I have only had this computer for a few months and have had problems since day one with the mail program not sending emails. The only thing added are the apple updates.


As for me asking a different question that the first one you are right but he didn't only ask how to reinstall the program he asked, "Is it possible that reinstalling Mail will solve the problem?" Actually that question has not been answered yet. He did get the program reinstalled but is not sure if it solved the problem.


Sorry but I feel my question is keeping in line with the basic problem that we both are having and feel it is appropriate.

May 14, 2011 6:47 PM in response to EricWeir

EricWeir wrote:


Is it possible that reinstalling Mail will solve the problem?

No. Reinstalling is a waste of time that will only cause new problems.


What e-mail server is this? It is likely just some flaky server. Have you made any modifications to your DNS system? Have you edited /etc/hosts? Have you checked your Console.app logs? Have you tried it in a new account to check for corrupt preference files?

May 15, 2011 8:27 AM in response to etresoft

etresoft wrote:

EricWeir wrote:


Is it possible that reinstalling Mail will solve the problem?

No. Reinstalling is a waste of time that will only cause new problems.


Too late. The reinstall is done. What problems should I expect?


What e-mail server is this? It is likely just some flaky server.


Are you asking about my ISP or server address? The ISP is AT&T with Yahoo email.


Have you made any modifications to your DNS system?


I have been using OpenDNS most of the time for the past year or so. The technician I hired tried setting the IPv4 configuration manually and experimented with different DNS addresses. The Genius Bar set it back to DHCP, which seemed to make a difference at the time. It's still set on configure by DHCP. I have the two DNS addresses given by OpenDNS and one given to me by the technician on my DNS address list.


Have you edited /etc/hosts?


Don't know what it is, so the answer is, No.


Have you checked your Console.app logs?


I did once, but there was so much information and I had no idea what to look for anyway.


Have you tried it in a new account to check for corrupt preference files?


Not sure what you mean by a new account. If you mean with an ISP, I've only got one. I wouldn't know how to go about creating another.


Regarding corrupt preference files, I guess this is not one of those situations in which you can simply delete the applications plist file and get a fresh one generated?



May 15, 2011 8:34 AM in response to Linc Davis

Linc Davis wrote:


I think one of the most common causes of problems with Mail is that people install third-party add-ons, or hacks as I call them, to modify its operation. The hacks may seem to work for a while, but eventually a system update makes them incompatible. The user forgets about them, doesn't update them, and doesn't associate them with his problem. That's why I advise anyone who has inexplicable problems using Mail to test it in safe mode.

I did try Mail Act-On briefly, possibly as much as a couple years ago. It is supposed to simpllify message filing and other actions on messages. I was interested in it for help in filing outgoing messages. I didn't find it that helpful and installed it not long after installed it. That was well before I started experiencing this problem.

May 15, 2011 9:08 AM in response to EricWeir

EricWeir wrote:


Too late. The reinstall is done. What problems should I expect?

If you just reinstalled the OS it shouldn't cause any problems. There are many suggestions online to try to replace just Apple Mail using Pacifist. The problem is never in the application bundle itself, so trying to replace it can only cause problems. Reinstalling the OS is the proper way to do it. It won't hurt anything, but it unlikely to help either.


Are you asking about my ISP or server address? The ISP is AT&T with Yahoo email.


I am talking about your SMTP address. You have at least two e-mail addresses. There is your IMAP/POP server for your incoming mail and your SMTP server for your outgoing mail.


Some ISPs don't like people connecting to any other SMTP servers but their own and will intercept any SMTP port 25 connections. Then, when you use your Yahoo credentials to try to connect to SMTP, the ATT server will intercept it and reject your login attempt. To avoid this, always configure your e-mail to use SSL. It is more secure anyway.


I have been using OpenDNS most of the time for the past year or so. The technician I hired tried setting the IPv4 configuration manually and experimented with different DNS addresses. The Genius Bar set it back to DHCP, which seemed to make a difference at the time. It's still set on configure by DHCP. I have the two DNS addresses given by OpenDNS and one given to me by the technician on my DNS address list.


I'll take that as a "yes". OpenDNS isn't bad. I don't like the idea of technician "experimenting". Who knows what else was changed.


Don't know what it is, so the answer is, No.

I'll take that as a "maybe not" since your technican could have done something too it. However, that is unlikely. I was more worried that you had taken some of the poor internet advice that recommends hacking up /etc/hosts.


I did once, but there was so much information and I had no idea what to look for anyway.


That is what we are for. Run Console.app and then try to trigger your e-mail problem. If the problem occurs, copy and paste the most recent Console.app entires here and we can tell you if there is something amiss than can be easily fixed.


Not sure what you mean by a new account. If you mean with an ISP, I've only got one. I wouldn't know how to go about creating another.


Regarding corrupt preference files, I guess this is not one of those situations in which you can simply delete the applications plist file and get a fresh one generated?


I mean a new account on your computer. Some of the preference files can be hard to track down. If you can reliably reproduce this problem on demand. Create a new account on your Mac, setup the e-mail the same way it is on the old account, and try to reproduce the problem. If you can't, then you can copy the most recently modified preference files in ~/Library/Preferences back to your home account. That is an easy way to fix preference files if you aren't sure which ones have problem or how to fix them.

May 15, 2011 9:30 AM in response to EricWeir

Eric, check out this thread:


https://discussions.apple.com/thread/2812583?tstart=0


Various useful information on the annoying issue you're dealing with, including correct configuration of ATT ports and servers, and links to other complaints about the same issue. Appears to be an ATT issue, but at least one person using Comcast noted the same problem.


My current "solution" when outgoing mail balks is to keep hitting "Try Again Using [the same outgoing server I used originally, as defined in Mail.app prefs]," and the message is usually sent in 2 or 3 tries. If not, quit and restart Mail, and message will go.


Incidentally, I reinstalled an older version of Mail.app from my installation DVD, updated with the 10.6.7 combo update, and it did not resolve the issue of intermittent sending issues.

May 16, 2011 7:08 AM in response to etresoft

Thanks for the informative response.


etresoft wrote:

I am talking about your SMTP address. You have at least two e-mail addresses. There is your IMAP/POP server for your incoming mail and your SMTP server for your outgoing mail.


Some ISPs don't like people connecting to any other SMTP servers but their own and will intercept any SMTP port 25 connections. Then, when you use your Yahoo credentials to try to connect to SMTP, the ATT server will intercept it and reject your login attempt. To avoid this, always configure your e-mail to use SSL. It is more secure anyway.


Throughout this process my incoming and outgoing servers have remained unchanged. And in mentioning AT&T/Yahoo I didn't mean to suggest that I had two sets. Yahoo is the email provider for AT&T. My SMTP address, e.g., is smtp.att.yahoo.com. Per AT&T's instructions the port for outgoing mail is 465. SSL is also used.

I have been using OpenDNS most of the time for the past year or so. The technician I hired tried setting the IPv4 configuration manually and experimented with different DNS addresses. The Genius Bar set it back to DHCP, which seemed to make a difference at the time. It's still set on configure by DHCP. I have the two DNS addresses given by OpenDNS and one given to me by the technician on my DNS address list.


I'll take that as a "yes". OpenDNS isn't bad. I don't like the idea of technician "experimenting". Who knows what else was changed.

Thanks for the reassurance about OpenDNS. I have been getting different reactions when I tell the people from whom I've been seeking help that I use it. And I believe the technician, whom I have used for years, did identify and, with AT&T's help, fix some associated internet connection problems. And when I switched over to the other two email clients I did not experience the problem one time.

I did once, but there was so much information and I had no idea what to look for anyway.

That is what we are for. Run Console.app and then try to trigger your e-mail problem. If the problem occurs, copy and paste the most recent Console.app entires here and we can tell you if there is something amiss than can be easily fixed.


I don't know how to trigger the email problem. [If I did, I might have a solution. -;) ] Can I take the alternative approach of checking Console entries when I experience the problem? Or does Console have to be running in order to log the events? If so, could I just keep it running the next few days till I know one way or another whether the problem has been solved by the reinstall? [I've not encountered it so far, but there hasn't been much outgoing mail the past couple days.]

Not sure what you mean by a new account. If you mean with an ISP, I've only got one. I wouldn't know how to go about creating another.

I mean a new account on your computer. Some of the preference files can be hard to track down. If you can reliably reproduce this problem on demand. Create a new account on your Mac, setup the e-mail the same way it is on the old account, and try to reproduce the problem. If you can't, then you can copy the most recently modified preference files in ~/Library/Preferences back to your home account. That is an easy way to fix preference files if you aren't sure which ones have problem or how to fix them.

I'm inclined to wait to try this till I experience the problem. And by "new account on your computer" I'm taking you to be referring to an internet connection account, i.e., to duplicating the current one under a different name to see if that solves the problem.


You say if it does to copy the recently modified preferences back to the home account. Since I would be duplicating the current account, couldn't I simply continue using it as my home account?


Thanks again,


Eric Weir

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Long-standing problem sending from Mail; will reinstalling help?

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