Apple Mail - fails to send and notifies me much later

[Verdanice]

Hey,

So Apple Mail has been driving me crazy lately. It's such a shame because it's such a slick program, but it looks like a couple of the problems I experience are not just problems for me but many users. For instance, accounts using SSL constantly asking for the password, often 4-5 times within a thirty second window.

One issue in particular has become too workflow crippling though. I have six email accounts in Mail, all POP3 (I need access to emails when I'm away from WiFi as well). My work email is set up to use my workplace's SMTP server, which belongs to the ISP of the office. Obviously, this means I can't send through this SMTP server when I'm not in the office. When I'm at home I just send through my personal SMTP server -- when I remember to specify that instead fo the office default before I send the email. When I forget, Mail usually won't say a word about its inability to send the email and I'll assume it's gone and continue about my day. In the following 24-48 hours, at some point, Mail will let me know it couldn't send the message. Up to two days later, by which point the lack of communication has already led to multiple problems, only worsening the headache. Mail insists on hiding the outbox 99% of the time, so when it gives up sending an email and doesn't prompt me, I have no way of knowing whatsoever short of calling whoever I emailed to confirm they've received.

It's pretty necessary that I use the office's SMTP server when I am in the office, so I can't switch the account over to just one SMTP server.. believe me, I would have done it a long time ago. Short of that, I can't find any other solution. I've been looking more and more into Postbox, but I'm not sure I'm ready to dive right in at the risk of screwing up my local/remote email syncing.

Has anybody experienced this? Any suggestions would be greatly appreciated, I'm tired of getting in trouble for failing to send important emails, and my boss is getting tired of the 'Apple Mail is incompetent' excuse.

 

[sidewinder]

It's pretty necessary that I use the office's SMTP server when I am in the office, so I can't switch the account over to just one SMTP server..

Care to explain why? Is it a technical reason or a policy reason?

S-

 

[Verdanice]

Care to explain why? Is it a technical reason or a policy reason?

S-

More because I don't like using my personal servers for work email (all it takes is a header check on the other end and they've got my personal site/email).

 

[sidewinder]

More because I don't like using my personal servers for work email (all it takes is a header check on the other end and they've got my personal site/email).

The header will not contain your personal email. It will contain the SMTP server used. But what is the problem with that? The only time people look at that is when troubleshooting...and most people don't know what they are seeing anyway.

Seems like a small issue considering all your problems would be solved.

S-

 

[Verdanice]

The header will not contain your personal email. It will contain the SMTP server used. But what is the problem with that? The only time people look at that is when troubleshooting...and most people don't know what they are seeing anyway.

Seems like a small issue considering all your problems would be solved.

S-

The X-Smtp-Server value in the header does contain my personal email address when I send through my personal SMTP server. The SMTP server is mail.mydomain.com as well, so that's my site.

Realistically, you're right, it shouldn't be an issue - but I really don't like to mix personal business with work in any capacity. If there's any way at all to avoid it I want to do what I can. It might very well mean switching to Postbox (more to alleviate myself of the SSH password prompts).

Thanks for the response.

 

[IJ Reilly]

I am confused by your description of the problem. For one since Mail doesn't have an "outbox" I don't know how it could be "hidden." If an e-mail isn't sent for some reason, Mail holds the e-mail in the Drafts folder. The most common cause of this seems to be when Mail can't send the SMTP server the correct authentication, normally a server-side issue. If Mail can't reach the SMTP server, you will be notified immediately and given the option of trying another. If the e-mail isn't being held in the Drafts folder, then in all likelihood the mail is being held by the SMTP server for some reason. That would explain why it is being bounced back after a day or two. I assume you are getting a bounce-back message, yes? If so, what does it say is the cause?

 

[Verdanice]

I am confused by your description of the problem. For one since Mail doesn't have an "outbox" I don't know how it could be "hidden." If an e-mail isn't sent for some reason, Mail holds the e-mail in the Drafts folder. The most common cause of this seems to be when Mail can't send the SMTP server the correct authentication, normally a server-side issue. If Mail can't reach the SMTP server, you will be notified immediately and given the option of trying another. If the e-mail isn't being held in the Drafts folder, then in all likelihood the mail is being held by the SMTP server for some reason. That would explain why it is being bounced back after a day or two. I assume you are getting a bounce-back message, yes? If so, what does it say is the cause?

Mail does have an outbox, and it is almost always hidden. It appears when you crash the program and it fails to finish sending something. What's happening is that mail will fail to send the email silently. No notification, the outbox won't appear.The only time email goes in the drafts folder is when you save it as you're composing or close and save without sending. This issue arises after clicking 'send'.

The messages are not bounced back, they never leave. I'm notified by Mail itself, not a delivery failure email, that sending with that server did not work, but far too late to be of any use.

 

[sidewinder]

The X-Smtp-Server value in the header does contain my personal email address when I send through my personal SMTP server. The SMTP server is mail.mydomain.com as well, so that's my site.

Realistically, you're right, it shouldn't be an issue - but I really don't like to mix personal business with work in any capacity. If there's any way at all to avoid it I want to do what I can. It might very well mean switching to Postbox (more to alleviate myself of the SSH password prompts).

Thanks for the response.

Why does you SMTP program add the X-Smtp-Server line with your email address in the header? You should be able to configure it not to do so.

You could just purchase authenticated SMTP service from some company and be done with it.

You are making this more difficult than it needs to be.

S-

 

[IJ Reilly]

Mail does have an outbox, and it is almost always hidden. It appears when you crash the program and it fails to finish sending something. What's happening is that mail will fail to send the email silently. No notification, the outbox won't appear.The only time email goes in the drafts folder is when you save it as you're composing or close and save without sending. This issue arises after clicking 'send'.

The messages are not bounced back, they never leave. I'm notified by Mail itself, not a delivery failure email, that sending with that server did not work, but far too late to be of any use.

From Mac Help:

About the Outbox mailbox
Mail shows the Outbox only when a message is waiting to be sent. Messages appear in the Outbox if you try to send a message when you’re working offline, or if Mail tried but was unable to send a message. The Outbox remains displayed until the message is sent or you quit Mail.

To edit an outgoing message or change the account you’re sending it from, double-click the message in the Outbox.

Still, I don't understand the problem. If Mail attempts to send an e-mail and fails due to a password or authentication issue, it warns you, asks if you want to try another server, or hold the message and try later. If you choose to hold the message, the Outbox appears and the message remains in it.

Do you see these "lost" messages in your Sent mail mailbox?

 

[Verdanice]

Why does you SMTP program add the X-Smtp-Server line with your email address in the header? You should be able to configure it not to do so.

You could just purchase authenticated SMTP service from some company and be done with it.

You are making this more difficult than it needs to be.

S-

I can appreciate it looks that way.. I don't have access to my SMTP server's settings, however.

Fact is, Mail isn't doing what it should be and I'm looking for a way to fix it, but I'm pretty doubtful that there's a way. I do appreciate your help, but I'm going to be somewhat stubborn though about using my personal SMTP as little as possible. Sorry, I know stubbornness is annoying from a helper's point of view, I do!

Still, I don't understand the problem. If Mail attempts to send an e-mail and fails due to a password or authentication issue, it warns you, asks if you want to try another server, or hold the message and try later. If you choose to hold the message, the Outbox appears and the message remains in it.

Do you see these "lost" messages in your Sent mail mailbox?

That's exactly the problem, it doesn't. It will sometimes, but most of the time it just won't say a word, and if I don't actually watch the message leave the outbox chances are it'll pop up in a couple days telling me it didn't send and to try another server. That is exactly the issue I am having, that it doesn't do what you've described, what it should do.

 

[IJ Reilly]

That's exactly the problem, it doesn't. It will sometimes, but most of the time it just won't say a word, and if I don't actually watch the message leave the outbox chances are it'll pop up in a couple days telling me it didn't send and to try another server. That is exactly the issue I am having, that it doesn't do what you've described, what it should do.

Specifically, do any of these messages show up in Sent mail? Assuming they don't, I'd try is this:

Deliberately create an unsendable e-mail (use a broken address like me@.com). You'll have to click "send anyway" twice. Then you should get the dialog box requesting you to try another server. Click "try later." This should create an Outbox, with the unsendable mail in it. Now, select the Outbox, and under the Mailbox menu, select "Rebuild."

 

[Verdanice]

Specifically, do any of these messages show up in Sent mail? Assuming they don't, I'd try is this:

Deliberately create an unsendable e-mail (use a broken address like me@.com). You'll have to click "send anyway" twice. Then you should get the dialog box requesting you to try another server. Click "try later." This should create an Outbox, with the unsendable mail in it. Now, select the Outbox, and under the Mailbox menu, select "Rebuild."

I've done that - what exactly was that meant to accomplish, though?

 

[IJ Reilly]

I've done that - what exactly was that meant to accomplish, though?

The only reason I can fathom for what you are seeing (or more accurately, not seeing) is a corrupted database index in Mail. If this is the problem, rebuilding the mailbox should help. Otherwise, I'm stumped.

 

[ppc750fx]

You could just move to Thunderbird. I've found it to be a better client anyways, with the sole exception of Spotlight support.

 

[superwoman]

I understand exactly your problem. My school has a pretty restrictive environment too. Specifially, it blocks outgoing port 25, which is becoming a more and more common restrictions. So when I'm at school, I *have* to use to school's SMTP server. Everywhere else, my school's SMTP server is inaccessible, and I have use either my ISP's SMTP server or Yahoo's server.

What I realize is that I need a multiple SMTP server configuration, where if one fails, there's automatic fallback to another. I don't think it's possible with Mail.app, or any email client (I'd be more then glad to stand corrected on this though).

So I use postfix, which is installed in all Mac OS X by default, as a SMTP relay. The last few lines of my postfix config file reads:

relayhost=<School SMTP Server name>
fallback_relay = mail.sbcglobal.net smtp.mail.yahoo.com
smtp_sasl_auth_enable=yes
smtp_sasl_password_maps=hash:/etc/postfix/sasl_passwd
smtp_sasl_security_options=
smtp_connect_timeout = 5s

What this says is tell postfix to do this: Try to connect to the school SMTP server first. Wait 5 seconds max. If that fails, fallback to my ISP's SMTP server, then Yahoo's SMTP server.

The smtp_sasl lines are for postfix to be able to login to the SMTP server.

Then the last thing I need to do is to configure all my mail accounts to use localhost as the SMTP server. So now, when I send mail, it gets sent to the localhost postfix first. Then postfix relays the mail by automatically trying each of those servers in turn. In my experience, postfix performs the relay immediately.

Unfortunately, I don't have a step-by-step for you. It's actually nothing more than standard postfix configuration. I'm sure it can be googled.

 

[IJ Reilly]

Maybe, but the real problem for the OP is that Mail is apparently not saving e-mails which fail to be sent in the Outbox, where they are supposed to live until Mail can connect with an SMTP server. Are you saying that you're seeing the same behavior?

 

[superwoman]

I can't say that I have or haven't seen this behaviour, because since I use postfix, I never have to deal with this kind of situation.

I'm just describing another way to solve his root problem, i.e. having to deal with multiple SMTP servers, and one that does not involve having to get to grips with Mail.app's UI.

 

[ppc750fx]

superwoman, do they also block 465 and 587? If not, you might be able to use one of those.

 

[superwoman]

superwoman, do they also block 465 and 587? If not, you might be able to use one of those.

Unfortunately, for my case, yes.

I can't even ssh out on a port other than 22, which is a problem for my home server. If I set it to listen on port 22, my ISP blocks incoming. If I set it up on a port other than 22, my school blocks outgoing. But I guess that's another story for another day...