I have a technical problem I am unable to fix on my own.
For some reason, Apple Mail (I’m on “Version 3.6 (936)”) has intermittently not sent email to some recipients from my lperson1@austin.rr.com account, a problem that started (I think) in late March. For a while I thought it might be rr.com’s fault, despite going through 2 layers of their generally unhelpful technical support, since they didn’t get down to the level of the Connection Doctor, didn’t seem to know how to do anything except follow their script, and said they couldn’t escalate me any further. (Thanks a lot, Time Warner.) However, I recently installed Thunderbird (which, I need to add, pretty much sucks) to isolate the problem, and it seems to send out the exact same messages fine, while the ones sent via Apple Mail never reach my email account, despite the settings for both being identical. The problem is especially frustrating, because the recipients it fail to send mail to tend to be the ones I communicate with most.
The problem in brief, along with the troubleshooting steps taken to resolve it:
- I’m on Mac OS X 10.5.8, and all my system software is up to date.
- I’m using normal SMTP over Port 25.
- I send an e-mail message to multiple recipients. None receive it.
- It still shows up in my Sent mail folder like all other mail.
- Emails to common recipients seem to fail more frequently than email to more occasional correspondents.
- I receive all my email just fine.
- I have not changed anything on my Linksys router or my cable modem. I have power cycled each at least once, and the iMac generally twice a day.
- I can send mail messages from the RR.com web interface just fine.
- I used to be able to send email to my gmail account just fine even after the problem started, but even that has been failing lately.
- It was working just fine April 16-17, then started malfunctioning again.
- I have a lot of email in my Inbox, and more saved in various other folders. As in over 10,000 messages, over 1,000 of which (usually some sort of notification) remain unread. But my Mail folder under Library takes up less than 2 GB, which doesn’t strike me as an inconceivable amount.
Here’s a Connection Doctor transcript of a message that didn’t go through (taking out line breaks between to make the code tag work properly, and omitting a couple of signature URLs for the same reason):
CONNECTED Mar 30 17:47:54.616 [kCFStreamSocketSecurityLevelNone] -- host:smtp-server.austin.rr.com -- port:25 -- socket:0x29233210 -- thread:0x291318a0
READ Mar 30 17:47:54.668 [kCFStreamSocketSecurityLevelNone] -- host:smtp-server.austin.rr.com -- port:25 -- socket:0x29233210 -- thread:0x291318a0
220 Welcome Road Runner. WARNING: *** FOR AUTHORIZED USE ONLY! ***
WROTE Mar 30 17:47:54.713 [kCFStreamSocketSecurityLevelNone] -- host:smtp-server.austin.rr.com -- port:25 -- socket:0x29233210 -- thread:0x291318a0
EHLO [192.168.1.101]
READ Mar 30 17:47:54.768 [kCFStreamSocketSecurityLevelNone] -- host:smtp-server.austin.rr.com -- port:25 -- socket:0x29233210 -- thread:0x291318a0
250-hrndva-omtalb.mail.rr.com says EHLO to 70.114.129.203:49710
250-8BITMIME
250-ENHANCEDSTATUSCODES
250 PIPELINING
WROTE Mar 30 17:47:54.773 [kCFStreamSocketSecurityLevelNone] -- host:smtp-server.austin.rr.com -- port:25 -- socket:0x29233210 -- thread:0x291318a0
MAIL FROM:
READ Mar 30 17:47:54.827 [kCFStreamSocketSecurityLevelNone] -- host:smtp-server.austin.rr.com -- port:25 -- socket:0x29233210 -- thread:0x291318a0
250 MAIL FROM accepted
WROTE Mar 30 17:47:54.829 [kCFStreamSocketSecurityLevelNone] -- host:smtp-server.austin.rr.com -- port:25 -- socket:0x29233210 -- thread:0x291318a0
RCPT TO:
READ Mar 30 17:47:54.925 [kCFStreamSocketSecurityLevelNone] -- host:smtp-server.austin.rr.com -- port:25 -- socket:0x29233210 -- thread:0x291318a0
250 RCPT TO accepted
WROTE Mar 30 17:47:54.929 [kCFStreamSocketSecurityLevelNone] -- host:smtp-server.austin.rr.com -- port:25 -- socket:0x29233210 -- thread:0x291318a0
RCPT TO:
READ Mar 30 17:47:54.982 [kCFStreamSocketSecurityLevelNone] -- host:smtp-server.austin.rr.com -- port:25 -- socket:0x29233210 -- thread:0x291318a0
250 RCPT TO accepted
WROTE Mar 30 17:47:54.985 [kCFStreamSocketSecurityLevelNone] -- host:smtp-server.austin.rr.com -- port:25 -- socket:0x29233210 -- thread:0x291318a0
DATA
READ Mar 30 17:47:55.039 [kCFStreamSocketSecurityLevelNone] -- host:smtp-server.austin.rr.com -- port:25 -- socket:0x29233210 -- thread:0x291318a0
354 continue. finished with "\r\n.\r\n"
WROTE Mar 30 17:47:55.043 [kCFStreamSocketSecurityLevelNone] -- host:smtp-server.austin.rr.com -- port:25 -- socket:0x29233210 -- thread:0x291318a0
Message-Id:
From: Lawrence Person
To: Dwight Brown
Content-Type: text/plain; charset=US-ASCII; format=flowed
Content-Transfer-Encoding: 7bit
Mime-Version: 1.0 (Apple Message framework v936)
Subject: Test 3/30 547PM
Date: Tue, 30 Mar 2010 17:47:54 -0500
Cc: lawrenceperson@gmail.com
X-Mailer: Apple Mail (2.936)
My guess it's still not working properly...
Lawrence Person
lperson1@austin.rr.com
.
READ Mar 30 17:47:55.097 [kCFStreamSocketSecurityLevelNone] -- host:smtp-server.austin.rr.com -- port:25 -- socket:0x29233210 -- thread:0x291318a0
250 OK 34/6E-03525-0AF72BB4
The intermittent (but ever-more-frequent) nature of the problem makes it hard to track down where the failure is occurring. (I'm wondeirng if some secret address cache has filled up and needs to be purged, but if so I don't know where it is.) The Apple help files don't cover it, and Google searches don't turn up my specific problem, at least that I can tell.
So, does anyone have any suggestions as to what is wrong, and how I go about fixing the problem? I would very much prefer to use Apple Mail rather than switching completely to Gmail.
Updated 5/25: An email specialist tells me that the relay information indicates it was successfully passed on to rr.com, and therefore is, in fact, their fault. I may have to fire their incompetent asses and go with AT&T instead.
Tags: Apple Mail, Roadrunner, Troubleshooting
Lawrence,
To pinpoint the issue being with your Mail settings on your user account on that Mac, or not:
– Set up a test user Accts on another Mac running the same Mac OS version.
– Set up a test Mail Acct using your email account.
– If it’s not an IMAP type of email Accts, ie. POP Accts, be sure to set the receive mail settings to Leave Mail On Server for a week.
– Test sen & receive mail.
– If all works fine, all or part of issue is in your Mail on your user Accts on your Mac.
– If same issues occur, you can rule you email Accts/user Accts/Mac.
It could be also a router issue. Some routers don’t interact with mail well.
Thus, test your Mac elsewhere to see if the problem is present.
I too am having the same problem. I am less capable technically than you seem to be, so I’ve not had any success in tracking down the problem.
I’m using an ISP in Australia.
I too am having the same problem. I am less capable technically than you seem to be, so I’ve not had any success in tracking down the problem.
I’m using an ISP in Australia.
I have the same problem and this is the log of the problem:
CONNECTED May 31 11:10:11.001 [kCFStreamSocketSecurityLevelNone] — host:smtp.utk.edu — port:587 — socket:0x1183726f0 — thread:0x11833cee0
READ May 31 11:10:11.504 [kCFStreamSocketSecurityLevelNone] — host:smtp.utk.edu — port:587 — socket:0x1183726f0 — thread:0x11833cee0
220 puma.mail.utk.edu ESMTP Sendmail 8.13.6/8.13.4; Mon, 31 May 2010 11:10:11 -0400
WROTE May 31 11:10:11.518 [kCFStreamSocketSecurityLevelNone] — host:smtp.utk.edu — port:587 — socket:0x1183726f0 — thread:0x11833cee0
EHLO [192.168.1.97]
READ May 31 11:10:11.586 [kCFStreamSocketSecurityLevelNone] — host:smtp.utk.edu — port:587 — socket:0x1183726f0 — thread:0x11833cee0
250-puma.mail.utk.edu Hello 99-17-83-158.lightspeed.knvltn.sbcglobal.net [99.17.83.158] (may be forged), pleased to meet you
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-8BITMIME
250-SIZE 104857600
250-DSN
250-AUTH LOGIN
250-STARTTLS
250-DELIVERBY
250 HELP
WROTE May 31 11:10:11.595 [kCFStreamSocketSecurityLevelNone] — host:smtp.utk.edu — port:587 — socket:0x1183726f0 — thread:0x11833cee0
STARTTLS
READ May 31 11:10:11.663 [kCFStreamSocketSecurityLevelNone] — host:smtp.utk.edu — port:587 — socket:0x1183726f0 — thread:0x11833cee0
220 2.0.0 Ready to start TLS
WROTE May 31 11:10:12.082 [kCFStreamSocketSecurityLevelTLSv1SSLv3] — host:smtp.utk.edu — port:587 — socket:0x1183726f0 — thread:0x11833cee0
EHLO [192.168.1.97]
READ May 31 11:10:12.151 [kCFStreamSocketSecurityLevelTLSv1SSLv3] — host:smtp.utk.edu — port:587 — socket:0x1183726f0 — thread:0x11833cee0
250-puma.mail.utk.edu Hello 99-17-83-158.lightspeed.knvltn.sbcglobal.net [99.17.83.158] (may be forged), pleased to meet you
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-8BITMIME
250-SIZE 104857600
250-DSN
250-AUTH LOGIN
250-DELIVERBY
250 HELP
WROTE May 31 11:10:12.161 [kCFStreamSocketSecurityLevelTLSv1SSLv3] — host:smtp.utk.edu — port:587 — socket:0x1183726f0 — thread:0x11833cee0
AUTH LOGIN
READ May 31 11:10:12.229 [kCFStreamSocketSecurityLevelTLSv1SSLv3] — host:smtp.utk.edu — port:587 — socket:0x1183726f0 — thread:0x11833cee0
334 VXNlcm5hbWU6
WROTE May 31 11:10:12.239 [kCFStreamSocketSecurityLevelTLSv1SSLv3] — host:smtp.utk.edu — port:587 — socket:0x1183726f0 — thread:0x11833cee0
ZGFuaWVsdHU=
READ May 31 11:10:12.307 [kCFStreamSocketSecurityLevelTLSv1SSLv3] — host:smtp.utk.edu — port:587 — socket:0x1183726f0 — thread:0x11833cee0
334 UGFzc3dvcmQ6
WROTE May 31 11:10:12.318 [kCFStreamSocketSecurityLevelTLSv1SSLv3] — host:smtp.utk.edu — port:587 — socket:0x1183726f0 — thread:0x11833cee0
************
READ May 31 11:10:12.412 [kCFStreamSocketSecurityLevelTLSv1SSLv3] — host:smtp.utk.edu — port:587 — socket:0x1183726f0 — thread:0x11833cee0
235 2.0.0 OK Authenticated
WROTE May 31 11:10:12.424 [kCFStreamSocketSecurityLevelTLSv1SSLv3] — host:smtp.utk.edu — port:587 — socket:0x1183726f0 — thread:0x11833cee0
MAIL FROM:
READ May 31 11:10:12.512 [kCFStreamSocketSecurityLevelTLSv1SSLv3] — host:smtp.utk.edu — port:587 — socket:0x1183726f0 — thread:0x11833cee0
250 2.1.0 … Sender ok
WROTE May 31 11:10:12.522 [kCFStreamSocketSecurityLevelTLSv1SSLv3] — host:smtp.utk.edu — port:587 — socket:0x1183726f0 — thread:0x11833cee0
RCPT TO:
READ May 31 11:10:12.593 [kCFStreamSocketSecurityLevelTLSv1SSLv3] — host:smtp.utk.edu — port:587 — socket:0x1183726f0 — thread:0x11833cee0
550 5.7.1 … Relaying denied. IP name possibly forged [99.17.83.158]
WROTE May 31 11:10:12.604 [kCFStreamSocketSecurityLevelTLSv1SSLv3] — host:smtp.utk.edu — port:587 — socket:0x1183726f0 — thread:0x11833cee0
QUIT
Thus far no solution and my ISP is ATT-Uverse
I also have the same intermittent problem… I’m in Central asia with a macBook hooked up through a cell phone. When I send to a Sometime when I send to one person it seems to send ok but they dont receive anything. Some times I send to a huge list of people and only some get it.
Is there another mail sending app. I can use that is simply reliable. I love the ease of use of ‘Mail’ but this is not acceptable.
Rudy
[…] TimeWarner’s continued incompetence, I’m slowly pulling all of my website from rr.com over to here. I now have the main Lame […]
Did you try setting the SMTP port to 465? IN Mail there is now a “use port: x,x,x” and one of them should be 465, but set it specifically to that and try again.
Since going 10.5.8 and Mail 3.6(936) the outgoing mail )sending time) has increased a lot (3 fold for small text messages). Not happy with that at all, especially if sending large files.
I think Apple has a Mail program problem they aren’t owning up to.
The problem is that it was an intermittent problem, which (along with the a complete lack of off-script knowledge among rr.com’s tech support channel) made it very hard to diagnose. I ended up switching everything over to Gmail.
I am also having trouble sending group emails. Sometimes they don’t send and I put them into my out box for later. When I restart Mail they go. It happens often. I have also been getting a number on my Mail icon on the dock indicating new mail when in reality there isn’t. I used MacKeeper to clean up my system of junk, verified and repaired permissions and cleaned out my logs, libraries and caches. I still have these problems and I’m on RR in NY.
I have been sitting here setting up accounts for 4 hours now. I have gone through every possible combination a problems solving solutions that I could, until my eyes were crossed. Mail has some really big issues. You fix one account, and the others stop working. It was a matter of rebuilding the mailbox, deleting passwords in the keychain, reentering passwords, quitting the program, reopening it. It is a completely random nonsensical error going on with the new mail 3.6.. It sucks. I give up. APPLE FIX THIS NOW!
hello, I also have this problem. Have researched everything and believe it is a software problem in Mail. If it won’t “send” try closing it, then reopening it, open the unsent mail in Outbox and click on send. If it goes through fine (& fast) you have the same problem we all do… Unresponsive Apple. They’ve moved on to Lion and other “pastures” trailing a junk MAIL program for others.
I also do have 3.6 Mail problems…..so frustrating and no help shame on apple.
I also just got road runner and can not use the email account. OS 10.5 and Mail 3.6. Even problems with bellsouth (AT&T) account. Wit no help from apple and Road Runner says it’s an Apple problem. 🙁
Apple wants to charge for the service call. When I objected I was hung up on. When Steve Jobs is gone Apple goes to hell!
Same thing happening overhere. Worked fine for 3 years and now i’m having the same problem…