When sending email, outgoing SMTP server keeps being rejected on first attempt

Jump to First Reply
Posted:
in Mac Software edited January 2014
The SMTP server I use for sending email had been working fine up until about a week ago. Although no changes were made to my setup, now virtually every time I send an email, I get the pop-up "Cannot send message using server xxxx".



When click on "Try with selected server" (the same server), it will then usually send okay; sometimes it takes an additional attempt.



Is this some keychain issue or something?



I've deleted the SMTP server and re-entered all the info, but it's still happening.



The SMTP server is the one from my ISP, so they should be okay with it.



Any ideas?



(PS I'm running Leopard 10.5.2)
«1

Comments

  • Reply 1 of 26
    Are you using Comcast? Try smtp port 587, this drove me nuts when they messed with the port numbers here.
     0Likes 0Dislikes 0Informatives
  • Reply 2 of 26
    argeliusargelius Posts: 309member
    Quote:
    Originally Posted by Sherman Homan View Post


    Are you using Comcast? Try smtp port 587, this drove me nuts when they messed with the port numbers here.



    Nope. I've got SBC (DSL). Really annoying....
     0Likes 0Dislikes 0Informatives
  • Reply 3 of 26
    mdriftmeyermdriftmeyer Posts: 7,503member
    Quote:
    Originally Posted by Argelius View Post


    Nope. I've got SBC (DSL). Really annoying....



    I know nothing of SBC and whether it's merger with ATT has you under SBC Yahoo ADSL or not, but if you do:



    http://helpme.att.net/article.php?item=285



    o locate and verify your email settings in Outlook Express:



    1. Click on the Tools menu in Outlook Express.

    2. Click on Accounts.

    3. Click on the Mail tab.

    4. Select your AT&T Yahoo! email account and click on the Properties button.

    5. Click on the Servers tab.

    6. Verify these settings:

    * For "My incoming mail server is a ____ server," the field contains POP3.

    * The Incoming mail (POP3) and Outgoing mail (SMTP) fields contain the correct mail server settings.

    * The Account name field contains your full AT&T Yahoo! email address (e.g., YourName@att.net).

    * The box next to Log on using Secure Password Authentication is NOT checked.

    * The My server requires authentication box is checked.

    7. Click on the Advanced tab.

    8. Verify these settings:



    Note: When updating the secure sever settings, check SSL checkbox first, then update the port number setting.

    * Under Outgoing mail (SMTP) should be port 465 and the box next to This server requires a secure connection (SSL) is checked.

    * Under Incoming mail (POP3) should be port 995 and the box next to This server requires a secure connection (SSL) is checked.

    9. Click OK.

    10. Click Close.
     0Likes 0Dislikes 0Informatives
  • Reply 4 of 26
    argeliusargelius Posts: 309member
    Quote:
    Originally Posted by mdriftmeyer View Post


    I know nothing of SBC and whether it's merger with ATT has you under SBC Yahoo ADSL or not, but if you do:



    * Under Outgoing mail (SMTP) should be port 465 and the box next to This server requires a secure connection (SSL) is checked.

    * Under Incoming mail (POP3) should be port 995 and the box next to This server requires a secure connection (SSL) is checked.

    9. Click OK.

    10. Click Close.



    Thanks. (I've got SBC yahoo, I believe). Unfortunately, the SMTP settings (465, SSL) are how I've had it set up and it's still taking 2-3 attempts to get email to send.



    I've tried deleting and rebulding the outgoing server info a couple of times, but to no avail.



    And for what it's worth, I'm having a similar problem on my iPhone (which has the same email accounts and settings).
     0Likes 0Dislikes 0Informatives
  • Reply 5 of 26
    outsideroutsider Posts: 6,008member
    If you have a google account, turn on pop in gmail and use their smtp server to see if that clears it up.
     0Likes 0Dislikes 0Informatives
  • Reply 6 of 26
    argeliusargelius Posts: 309member
    Quote:
    Originally Posted by Outsider View Post


    If you have a google account, turn on pop in gmail and use their smtp server to see if that clears it up.



    Thanks Unfortunately, I use sbc/AT&T as my ISP.



    Other people I know who are using the same SMTP settings with Mail on 10.5.2 are having no problems.



    It's an odd behavior in that mail messages will send after the second or third attempt.
     0Likes 0Dislikes 0Informatives
  • Reply 7 of 26
    mdriftmeyermdriftmeyer Posts: 7,503member
    Quote:
    Originally Posted by Argelius View Post


    Thanks. (I've got SBC yahoo, I believe). Unfortunately, the SMTP settings (465, SSL) are how I've had it set up and it's still taking 2-3 attempts to get email to send.



    I've tried deleting and rebulding the outgoing server info a couple of times, but to no avail.



    And for what it's worth, I'm having a similar problem on my iPhone (which has the same email accounts and settings).



    Try 587 and if that craps I'd drag out your SMTP certificate form KeyChain and after Restarting and connecting to your Server see if the SMTP authentication adds a new Certificate for you.



    I assume you've checked to make sure none of them have expired, correct?
     0Likes 0Dislikes 0Informatives
  • Reply 8 of 26
    argeliusargelius Posts: 309member
    Quote:
    Originally Posted by mdriftmeyer View Post


    Try 587 and if that craps I'd drag out your SMTP certificate form KeyChain and after Restarting and connecting to your Server see if the SMTP authentication adds a new Certificate for you.



    I assume you've checked to make sure none of them have expired, correct?



    I don't know why I didn't think to do that. I first checked in keychain that all the certificates were trusted and not expired. Still didn't work. Then I deleted every "smtp" listing in Keychain Access and voila! All is good now.



    Thanks for pointing me in the right direction!
     0Likes 0Dislikes 0Informatives
  • Reply 9 of 26
    mdriftmeyermdriftmeyer Posts: 7,503member
    Quote:
    Originally Posted by Argelius View Post


    I don't know why I didn't think to do that. I first checked in keychain that all the certificates were trusted and not expired. Still didn't work. Then I deleted every "smtp" listing in Keychain Access and voila! All is good now.



    Thanks for pointing me in the right direction!



    You're welcome. To me it's one of those spurious bugs in KeyChain that it doesn't periodically check for duplicates and/or expiration dates and let the user know when applications like Mail are leveraging them.
     0Likes 0Dislikes 0Informatives
  • Reply 10 of 26
    I've been dealing with this problem for over 2 weeks on my 10.5.2 laptop. Sends can fail 2, 3, 4, 5 times and then finally go through after I keep hitting try again. And then a bunch will go through fine first time. Finally called AT&T DSL support and got nowhere since it's an intermittent problem. They couldn't duplicate it. They said it's an OSX issue although the 2nd level tech guy I got through was not knowledgeable.



    This just started happening on another 10.4.11 machine so I figured it's got to be AT&T but then found this thread. However, on both machine's there's no certificate for the smtp server in Keychain Access. I tried deleting the login items but no dice. Immediately failed again on my next test send.



    Any other ideas or pointers?
     0Likes 0Dislikes 0Informatives
  • Reply 11 of 26
    argeliusargelius Posts: 309member
    I finally got the issue escalated to 3rd level tech support with ATT. Whomever I spoke to seemed to acknowledge it was a problem they were aware of and would get back to me "within 4 days..."



    Will wait and see.
     0Likes 0Dislikes 0Informatives
  • Reply 12 of 26
    litzlitz Posts: 1member
    I have exactly the same issue. It just started all of a sudden on Friday (3/28). I spent an hour on the phone with my ISP (a local company, not AT&T or Comcast or Bellsouth) trying to figure out what's going on and all they could guess is that it's some kind of firewall. I'm using Leopard as well. It's very frustrating.



     0Likes 0Dislikes 0Informatives
  • Reply 13 of 26
    danseqdanseq Posts: 2member
    I'm still in Tiger and this has been driving me nuts. It seems to be worse tonight in that unlike previous days where I could get something to send after a few attempts, I can't seem to send them at all now.



    Anyone have any news?
     0Likes 0Dislikes 0Informatives
  • Reply 14 of 26
    argeliusargelius Posts: 309member
    Quote:
    Originally Posted by danseq View Post


    I'm still in Tiger and this has been driving me nuts. It seems to be worse tonight in that unlike previous days where I could get something to send after a few attempts, I can't seem to send them at all now.



    Anyone have any news?



    Well, it seems to be getting worse.



    In my dealings with ATT technical support, they had me switch to Port 25 with no SSL (was previusly at 465 with SSP).

    That didn't really improve things -- still could send 95% of the time on the second "try again".

    This morning, I can't send anything -- on either port.



    This is also happening on my iPhone and a windows PC at work, so I know the issue lies with ATT.
     0Likes 0Dislikes 0Informatives
  • Reply 15 of 26
    argeliusargelius Posts: 309member
    Well, when I got up this morning, I couldn't send emails at all -- on either port 25 or 465 (with out without SSL).



    Did a little researching on the internets and tried this:



    smtp.mail.yahoo.com

    on port 465 with SSL.



    And it works!



    It works now on the first send attempt. (Also works on my iPhone)



    Hope this may help someone else...
     0Likes 0Dislikes 0Informatives
  • Reply 16 of 26
    danseqdanseq Posts: 2member
    Quote:
    Originally Posted by Argelius View Post


    Well, when I got up this morning, I couldn't send emails at all -- on either port 25 or 465 (with out without SSL).



    Did a little researching on the internets and tried this:



    smtp.mail.yahoo.com

    on port 465 with SSL.



    And it works!



    It works now on the first send attempt. (Also works on my iPhone)



    Hope this may help someone else...





    Hurrah!! Thank you thank you! It works... both on my iphone and my regular mac mail.



    Of course 1st tier tech support told me (twice) it wasn't their fault and check my other web host.



    Weak.
     0Likes 0Dislikes 0Informatives
  • Reply 17 of 26
    Hello all,



    I also have been having problems with the outgoing mail server through att dsl. These problems have been cross platform (mac (Tiger) & pc (windoz XP pro)) and over multiple email programs (Outlook 2003 & Mail). Even with using the correct ports and SSL settings (smtp.mail.yahoo.com on port 465 with SSL) I still get bounce backs for 3 or 4 tries and then the message finally goes through. After digging around a bit I found this page on att dsl's site.



    http://help.yahoo.com/l/us/yahoo/mai...ndfrom-07.html



    Essentially, you need to register all of your other email addresses with ATT in order for them to allow you to use their smtp server seemlessly. It's really a joke. Coming from Comcast Cable Modem I could use many different SMTP servers (each based on the specific email account (.mac, gmail, other pop accounts, etc). Switching DSL I was forced to use their smtp server for all of my various email accounts. Then, they change the rules on me without telling anyone and force us to register each email address through their online webmail settings. The explanation I was given by one of their tech support people is that they are changing their email system and have put these new rules in place (again, without telling anyone) to limit spam.



    After I registered each of my family's 7 email accounts (only one of which is an ###@att.net) all of my email accounts work seemlessly and can send emails without getting bounce rejections.



    What a bunch of hoops to jump through just to use this slow (compared to cable modem) broadband. If only it wasn't half the price of cable modem.
     0Likes 0Dislikes 0Informatives
  • Reply 18 of 26
    sequitursequitur Posts: 1,910member
    I reported that I had this problem on another thread, but have had no luck in fixing it. I've talked to 2nd tier at Comcast twice, checked Apple's site, read email Apple sent to fix it. NO Luck.



    I've had the problem about two weeks, and I realize how important Mac Mail is to me. Going online to send email is a real pain.
     0Likes 0Dislikes 0Informatives
  • Reply 19 of 26
    sequitursequitur Posts: 1,910member
    I noticed that although I set the 'Authentication' field on the Outgoing Mail Server page to 'Password', it showed 'None' when I happened to go back to that page. I changed it back to 'Password' again, but this time, I typed in my User name and Password in those fields (even though it states that you don't have to do that). Server port is 587 and SSL is unchecked. As I clicked OK, all of the messages in my outgoing box went whoooosh and were sent.



    Another thing I changed was the in the Description field on the Account information page. I changed it from POP account to Comcast E-Mail. I seriously doubt that made any difference, but if the above paragraph doesn't work, try adding a like description in that field.



    If you try this, please let me know if it works for you. Wow! Two weeks of frustration gone.
     0Likes 0Dislikes 0Informatives
  • Reply 20 of 26
    argeliusargelius Posts: 309member
    I subsequently found out a bit more information from ATT which, I believe, has permanently (?) fixed the SMTP/mail sending problem.



    I have SBC/ATT DSL and had been using smtp.sbcglobal.yahoo.com as my SMTP server. While some of the fixes noted above, helped the situation, I would still receive fairly regular "unable to send using the selected server errors."



    Once I got through second-level support with ATT I found that unbeknownst to me, they had made a change that required all email domains to be used with their smtp sever to be "registered".



    I went into the yahoo email address associated with my DSL service (which I had never done since I have my own email domain). There's a place there is authenticate all the emails with which you want to use ATT's SMTP server. From the yahoo email account you send an email to each of the emails you want to authenticate; these subsequently receive a code that you then enter on the yahoo mail system.



    Since I did that (along with switching to smtp.att.yahoo.com (465, SSL), everything is working 100% of the time. Not sure if Comcast (or other internet providers) are doing something similar...



    This link has more info about this: http://help.yahoo.com/l/us/yahoo/mai...ndfrom-07.html
     0Likes 0Dislikes 0Informatives
Sign In or Register to comment.