send me packing

August 7, 2011 2:38 PM

For several days I had an intermittent problem sending email from my Mac Mail program. I have three addresses set up through the program, including my main account (from my own website) that i have used for more than two years. Now the smtp is rejecting me.

Nothing has changed in my settings, and when I called my ISP to explain the message said "your iSP is rejecting your address" they gave me helpful advice including "get a Mac specialist" and "try webmail". I have found that if I change my IP address each time I send, then it is okay. But I cannot send twice from the same IP address. And eventually they will run out. Can anyone tell me what could be causing this, or what to say to my ISP (it is Orange, I am in France) that will encourage them to consider the problem and not dismiss me.

Thanks.

posted by bwonder2 to Computers & Internet (10 answers total)

What is the exact error you are getting when the message bounces back?
posted by dgeiser13 at 2:58 PM on August 7, 2011

Response by poster: Something like "smtp rejected the sender addresse. That is not verbatim -- but it basically says it is the address, and I've tried with all my accounts, all are rejected with the same sporadic intervals, though it has become more difficult to send. Now I can send one email, and for the next I need to change my IP.
posted by bwonder2 at 3:06 PM on August 7, 2011

Did your ISP maybe switch SMTP to a secured port? In your mail settings, is the outgoing server set to port 587? Secure Sockets Layer (SSL)? Or STARTTLS?

I have almost no idea what I just said, so I would write everything down or take a screengrab before changing the settings.
posted by steef at 3:43 PM on August 7, 2011

Mail has a "Connection Doctor" feature that will show you the raw messages sent to and received from the mail server as it tests your ability to send. It's pretty much unusable if you have a half-dozen accounts, as I do.

When I need to debug sending mail, I often use Terminal.app to do so.

This page describes how to do so if you don't need a user/password to send mail:
http://www.anta.net/misc/telnet-troubleshooting/smtp.shtml

This page describes how to do so if your mail server requires auth:
http://www.webpan.com/Customers/Email/SMTP_Authentication_Telnet_Test.htm
posted by Mad_Carew at 3:55 PM on August 7, 2011

Response by poster: I've tried different ports, and the ISP swears they've changed nothing. I've pretty much tried all combinations of settings, automatic ports, 25, 587 and 465.
posted by bwonder2 at 3:57 PM on August 7, 2011

Are they using something like POP before SMTP? Is each ip you change to a previously unseen IP? That is the odd part. You should telnet to port 25 as Mad_Carew mentioned and try to send email manually to get the exact error the SMTP server is giving.
posted by Ad hominem at 4:17 PM on August 7, 2011

Sometimes you get mail authentication problems if your keychain (where the passwords are stored ) gets corrupted. Try removing the keychain entries for the accounts you access in Mail. Then launch Mail and have the program recreate the keychain entries. If there is a problem with your keychain entries, an incorrect password stored, or duplicate entries for the same account, then this can sometimes cause problems.

Something similar happened to me once and the keychain solution worked.
posted by Poet_Lariat at 5:08 PM on August 7, 2011

Oh! I've had this problem! It's because Gmail doesn't like when you use IMAP to set up the same account on lots of different mail clients/computers. This happened to me because I have several home computers as well as several work computers and my iPhone. When I set up my email on a new computer the most recent time, I got this error. So, did you recently set up a different account (a work account, maybe) on this computer and have it set up on a bunch of other computers, too? That's my guess.
posted by two lights above the sea at 5:59 PM on August 7, 2011

Oh, and as far as a solution: I had to stop using one of the other computers for mail. The problem resolved itself after that.
posted by two lights above the sea at 6:00 PM on August 7, 2011

Response by poster: Thanks everyone. I deleted all the passwords in my Keychain, still didn't work, checked Terminal, gave me nothing, shut the computer down and opened it again (for like the fifth time) and now it's working!
I have no idea what changed (I am afraid to even type this message, in case the gremlins come back).

twolightsabovethesea, I didn't add a new account, I didn't change anything. It was just like my computer got fundamentally tired of sending email!

Thanks again.
posted by bwonder2 at 4:42 AM on August 8, 2011