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Old Feb 6, 2012, 12:13 PM   #1
pat park
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Mac mail won't send stays in Outbox

Have 10 messages in my outbox that will not send. They stay in the outbox the send folder keeps spinning and nothing is helping.

Restarted numerous times.
Deleted the mail accounts, recreated accounts again. Can receive but cannot send.

Why is Mac Mail so weird ?

Latest version of Lion 10.7.3
MBP 13 late 2011. 8gb ram. No other issues except for Mac Mail.
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Old Feb 6, 2012, 01:42 PM   #2
pat park
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just started sending again. No rhyme or reason, it just stops then when it feels like it, starts working again.

arrgghh!!
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Old Feb 6, 2012, 02:58 PM   #3
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Sounds like an error on your provider's side with accepting the SMTP protocol or authorization. Sometimes they have issues and deny connections to send.
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Old Feb 7, 2012, 12:14 AM   #4
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Or maybe your mail provider is experiencing a service outage.
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Old Feb 7, 2012, 09:34 AM   #5
pat park
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this is a Lion problem. It just comes and goes.

Getting sick of this crap. I've been preaching the virtues of Mac since last year and now I cannot send messages. This is great for video work and sound work, but for basic business stuff like sending emails it fails.

This all started with 10.7.3 update. The mail issue starts whenever. No rhyme or reason.

No one else on this forum has experienced this same problem? Google it and you see many threads (with no real solutions other than wait it out, it eventually comes back on its own).
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Old Feb 7, 2012, 09:39 AM   #6
rowley
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always been my provider with the problem.
Have you tried an alternative smtp service?
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Old Feb 7, 2012, 11:15 AM   #7
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I have never has an SMTP problem with Mail on any version of Lion. Nor have I had SMTP issues with Thunderbird. I have used both a Gmail SMTP server and a smaller ISP SMTP server.

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Old Feb 7, 2012, 11:34 AM   #8
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Quote:
Originally Posted by pat park View Post
this is a Lion problem. It just comes and goes.

Getting sick of this crap. I've been preaching the virtues of Mac since last year and now I cannot send messages. This is great for video work and sound work, but for basic business stuff like sending emails it fails.

This all started with 10.7.3 update. The mail issue starts whenever. No rhyme or reason.

No one else on this forum has experienced this same problem? Google it and you see many threads (with no real solutions other than wait it out, it eventually comes back on its own).
I am not questioning your experience, but why does everyone feel that it is always a Lion problem (but you said it worked fine before, so it is an update issue if any and not a Lion issue). Maybe something got slightly corrupted during your upgrade. If you already knew it was a Lion upgrade issue, then why not state this along with some other information that may help people troubleshoot this with you. I have several accounts and have no issues with any of the accounts (they vary from MSN Live, GMAIL, work exchange, and personal IMAP run from a Lions server). None have any issues sending or receiving.

We have no idea what your configuration is or how it is being used. If you would like some help, then you need to state some setup information and any errors you are getting. Have you forced the connection during these down times. What have you done to troubleshoot it (other than Googling, which is a good idea)? Without knowing what you have tried, we can't help you. Bear in mind that lots of the people that visit this forum are not the average user, so we tend to not get the same issues as the average user, as our systems are configured and maintained different than the average user.
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Old Feb 7, 2012, 12:51 PM   #9
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sorry guys. I am so frustrated with this issue. My Macs have worked flawlessly for the past year and out of nowhere it just started up.

Gmail - using gmail outgoing servers
Internet service provided by AT&T - tried using the ATT smtp and nothing.

sent messages just spins, the outgoing box is full of unsent mail. I do have imap enabled on my Gmail account. This was all working with no issues and just stops working with no warning.

searched Google and really found no real answers other than, delete your mail account, add it back and the problem goes away, temporarily.
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Old Feb 7, 2012, 12:57 PM   #10
sidewinder
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Quote:
Originally Posted by pat park View Post
Gmail - using gmail outgoing servers
What are your settings?

I use:

Server Name: smtp.gmail.com
Use Custom Port: 465
"Use Secure Sockets Layer (SSL)" is checked.
Authentication: Password

Username: The main address for the gmail account.
Password: my gmail password

I never have a problem.

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Old Feb 7, 2012, 01:12 PM   #11
pat park
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Quote:
Originally Posted by sidewinder View Post
What are your settings?

I use:

Server Name: smtp.gmail.com
Use Custom Port: 465
"Use Secure Sockets Layer (SSL)" is checked.
Authentication: Password

Username: The main address for the gmail account.
Password: my gmail password

I never have a problem.

S-
exactly what I have. weird.
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Old Feb 7, 2012, 01:19 PM   #12
sidewinder
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Pat,

What do you get back when you type this in Terminal?:

telnet smtp.gmail.com 465

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Old Feb 7, 2012, 01:25 PM   #13
pat park
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It just started working after deleting and adding back all my email accounts.

The terminal comes back with this:

Last login: Tue Feb 7 11:03:11 on console
Patricks-MacBook-Pro:~ patpark1$ telnet smtp.gmail.com 465
Trying 74.125.53.109...
Connected to gmail-smtp-msa.l.google.com.
Escape character is '^]'.
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Old Feb 7, 2012, 01:52 PM   #14
pat park
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was working for a few minutes, now the outgoing box is missing and sent messages just disappear!!!

great!
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Old Feb 7, 2012, 02:01 PM   #15
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Have you try the Mailbox>Rebuild option?

Which version of 10.7.3 did you install, the combo or the delta update? If you are having issues since the update, it might be worth it to try and reapply the combo update and try and verify/ repair permissions (as sometimes they can change and cause issues after an update)?
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Old Feb 7, 2012, 02:04 PM   #16
pat park
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Quote:
Originally Posted by squeakr View Post
Have you try the Mailbox>Rebuild option?

Which version of 10.7.3 did you install, the combo or the delta update? If you are having issues since the update, it might be worth it to try and reapply the combo update and try and verify/ repair permissions (as sometimes they can change and cause issues after an update)?
installed the combo update day after I installed the delta. I had no issues with the delta, but did the combo just to be safe.
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Old Feb 7, 2012, 03:00 PM   #17
pat park
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Downloaded Thunderbird, yuck!

Tonight I will uninstall and reinstall Mac Mail and hope this will solve the issues. This is so strange and many of my tech friends are all stumped.
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Old Feb 7, 2012, 08:31 PM   #18
pat park
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repaired disk permissions - had a ton of weird mismatched things going on here.

deleted all mail accounts, added them all back

changed Sharing & Permissions to read & write (get info on Mail icon in finder)

restarted laptop, launched mail, all seems to be working - for now.
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Old Feb 7, 2012, 09:00 PM   #19
pat park
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crap, it's doing it again.

messages stuck in outbox. won't send.

I'm done with Mac Mail. Too finicky for me.

Sparrow for now I guess.

Can I uninstall Mac Mail and reinstall it again? My MBP 13 is a late 2011 and no discs came with it.
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Old Feb 8, 2012, 09:04 AM   #20
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dude Lion is probably the culprit. not being a hater here, but I have had more Lion problems than any other version of OS X. Even the fanboys here cannot deny it. It's like Vista. It's that bad, or at least it seems that bad to us, since we (OS X users) are so used to everything working perfectly.
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Old Feb 8, 2012, 10:07 AM   #21
rkaufmann87
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Quote:
Originally Posted by pat park View Post
Have 10 messages in my outbox that will not send. They stay in the outbox the send folder keeps spinning and nothing is helping.

Restarted numerous times.
Deleted the mail accounts, recreated accounts again. Can receive but cannot send.

Why is Mac Mail so weird ?

Latest version of Lion 10.7.3
MBP 13 late 2011. 8gb ram. No other issues except for Mac Mail.
No one has mentioned Apple's solution as documented in:

http://support.apple.com/kb/TS1307

I've had this come up from time to time and this solution works every time.
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Old Mar 1, 2012, 09:35 AM   #22
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Unhappy Originally Posted by pat park Have 10 messages in my outbox that will not send. Th

I have this problem as well but it happened on my mac before I installed Lion. Have installed Lion now (hoped it might solve the issue) but outgoing mail is still stuck. Don't know why it's happened - server settings all correct. Apple now trying to see if they can fix it.
Have done everything so far suggested by

http://support.apple.com/kb/TS1307

(((
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Old Mar 2, 2012, 11:53 PM   #23
bruceko
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I have been having the same problem starting about 2 weeks ago with one account on one computer.

The same email account works fine on our other computers.
I finally turned off SSL and it would send again.
On the other computers if I turn off SSL mail won't send
Weird
I talked to apple and they have no clue
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Old Mar 9, 2012, 06:43 AM   #24
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Same problem for me - went to bed last night all working, woke up this morning and not working! Nightmare. repaired permissions, restarted - even tried crossing my fingers and walking under a ladder still no joy! It works fine from phone or iPad, so I can't imagine it being server outage or incorrect passwords as it keeps telling me. I'm running OS 10.7.3 download from app store.

I've wasted a half a day so far on something that should just work ....

Come on Apple, pull your fingers out and get this sorted
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Old Mar 9, 2012, 11:04 AM   #25
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"sorry guys. I am so frustrated with this issue. My Macs have worked flawlessly for the past year and out of nowhere it just started up.
Gmail - using gmail outgoing servers
Internet service provided by AT&T - tried using the ATT smtp and nothing"

I'm coming into this thread a little late, but I'll try to help. This is a long post, please save it and/or print it out.

Pat park -- you said you're with ATT, so am I. In fact, after using ATT dsl for a decade, I just switched over to ATT Uverse about 10 days ago, and that's when my own "can't send email" problems began.

You aren't alone, MANY Mac users have the same problems, particularly with ATT Uverse.

ATT blocks "port 25" by default. This is the normal "outgoing" port for email (the "smtp" parameter you enter).

There are other "out" ports (may be port 587?), some folks experience success using them, but others don't. I tried -all kinds- of re-configurations to try to get Mail.app to work with my new Uverse setup, and couldn't. I suspect that the reason I couldn't "get through" is because my email address is tied to a "legacy server" ("xxx@snet.net"), instead of being simply "xxx@att.net".

Interestingly, I found that if I used Thunderbird to send email (instead of Mail.app), the outgoing email would send without problems, even though all the account parameters were the same.

I've come to the conclusion (based on my own hunches, I'm not a software expert) that there is -something- in Mail.app that can't "let go of" port 25, even when you specify a different outbound port for email. Or, it may be in the way Mail.app combined with the Keychain handle the [host] server's password query. Thus, even though you've configured it to send to a different smtp port, Mail.app is still trying to "touch" port 25, and because ATT blocks port 25, the whole process of sending mail grinds to a halt.

There is a very easy way to cure this problem:
Contact ATT and have them TAKE THE BLOCK OFF port 25 for your account.

Once I did that, my email problems with ATT -DISAPPEARED-, and things are back to normal.

HOWEVER -- it can be VERY difficult to contact ATT and get this resolved. You have to know the right number to call, the right things to say. Keep reading.

By phone, the number you want to call is 866-757-9808. This is "tier 2" tech support. Ignore the "press 1 for xxx" at first, then wait. You should hear something to the effect "if you are tier 1 tech, press 1". THIS is what you want to do, so press 1. You should next reach a level-2 tech.

Give him/her your account info. Then explain that you are a Mac user, that you can't send outgoing mail, that you have tried alternate ports and that they don't work. Specifically request that port 25 be "un-blocked" for your account. It has been recommended that the language to use is "I would like SMTP outbound on port 25 unblocked".

The tech person is probably going to resist doing this. You may be told something to the effect, "I can do that, but it might be questioned if I did". Then you might be told that you need to be connected to something called "Connect Tech". DO NOT LET THEM DO THIS, the Connect Tech is a scheme to get you to subscribe to a $15 per month service contract. YOU DO NOT NEED THAT. All you need is to have port 25 un-blocked.

I didn't know this at first, so I let them forward me over. When I talked to the ConnectTech and found they wanted to sell me something, I ended the conversation immediately.

It's possible that (knowing more than I did the first time) you -may- succeed in getting the Tier 2 tech to take the block off. Be aware that I've heard of them charging a one-time $29 fee for this. I didn't end up paying it, perhaps others have, but if they had told me I would have to pay that, I would have paid, for ultimately removing the block was the only way my email would work.

I have an email address (that I haven't used) that -might- help you:
uversecare@att.com
In the subject line put the following: [Trouble]
(again, I haven't used this, and if you can't get outbound email to work, it won't help!)

What finally worked for me:
I managed to contact an ATT tech support person (probably in S. Asia) using their "live chat" feature, which you can find at this URL:
https://pattta.att.motive.com/netage...re_uverse.aspx

Again, I went over the problem, explained I was a Mac user, emphasized that I was using a legacy (3rd-party?) server instead of "att.net", and requested that port 25 be un-blocked for my account.

The tech person said they would take the block off, did so, and verified that it was off.

Since that time, my Uverse outbound email now sends immediately without problems.

Perhaps this will work for you, and for anyone else reading this who uses ATT Uverse.

Last edited by Fishrrman; Mar 9, 2012 at 12:07 PM.
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