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.
