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Cannot send e-mail

Hi


I upgraded to OS X Yosemite a couple of days ago and today my e-mail stopped working. I have a POP account and use a Plusnet account. I've managed to restore the incoming e-mail but continue to not be able to send e-mail.


I've searched through the Apple support forum and other internet forum and have tried some of the suggestions for dealing with Mail issues such as disabling the automatic detect and maintain account settings options and have allowed insecure authentication. I have also spoken to my e-mail/internet provider and they could not resolve the issue on their end.


I'm using port 587 (which the e-mail provider confirms is correct), have unchecked SSL and the e-mail and account details all seem fine.


Could anyone suggest anything that might get sending e-mails using Mail working again? Should I revert to Mavericks (if this is possible) where I had no problems with Mail?


Many thanks

MacBook Pro (13-inch Mid 2009), OS X Yosemite (10.10)

Posted on Nov 2, 2014 1:09 PM

Reply
39 replies

Nov 3, 2014 11:59 AM in response to Linc Davis

Hi Linc


Many thanks for your response. I went through all of the document and I still can't get my e-mail sending to work (I can receive e-mails). I had no issues before installing OS X Yosemite and it's unclear to me whether this needs a OS fix or whether there is a solution to this issue


Any further thoughts would be much appreciated.


Many thanks

David

Nov 4, 2014 11:28 AM in response to Linc Davis

Hi Linc


This is what I've tried (bearing in mind that I've had my internet provide remotely connecting to my computer to check all my settings and they could not work out what the issue was as all settings were re-input):


- Under connection doctor, the STMP account type is showing a red status, the error message is: 'Trying to log in to this STMP account failed. Verify that the username and password are correct'. Both have been verified as correct. The network diagnostics box is greyed out and cannot be access directly from connection doctor


- Checking network diagnostics shows that the status is green for everything


So going to the part of the document that looks at where the connection doctor shows one or more red dots in the account status column:


- Check your incoming IMAP or POP and outgoing STMP email account settings: these have been checked both by myself and my internet provider as correct

- I have no third party software so this can't be causing any issues

- Check for Internet Service Provider port blocking: I have checked this per the instructions and this looks fine; in case it matters, I am using port 587 rather than 25 as advised by my internet provider (although the issue remains whether I use port 25 or 587

- I am connected to the internet from my normal location and using the same ISP as usual

- I have no icon next to my inbox (there was at one point but I solved this through allowing insecure authentication (which I did reluctantly)

- I've tried webmail and this works fine, both receiving and sending e-mails

- I have not reset my e-mail account or password and I'd rather not as it's not obvious that this will resolve the issue


There are no other options in the steps set out in the article so I'm at a loss as to what to do. Very frustrating.


If it's useful, I can set out the log details from the Mail connection doctor.


Thanks in advance for further help

David

Nov 4, 2014 12:17 PM in response to David1248

Triple-click the word "telnet" in the line below on this page to select the whole line:

telnet relay.plus.net 587

Copy the selected text to the Clipboard by pressing the key combination command-C.

Launch the built-in Terminal application in any of the following ways:

☞ Enter the first few letters of its name into a Spotlight search. Select it in the results (it should be at the top.)

☞ In the Finder, select Go Utilities from the menu bar, or press the key combination shift-command-U. The application is in the folder that opens.

☞ Open LaunchPad. Click Utilities, then Terminal in the icon grid.

Paste into the Terminal window by pressing command-V. I've tested these instructions only with the Safari web browser. If you use another browser, you may have to press the return key after pasting.

You should almost instantly get three or more lines of output below what you entered, one of which is this:

Escape character is '^]'.

If there's no output within ten seconds, consider that a failure. If you get something different from the above, please post it in a reply. You can then quit Terminal.

Nov 4, 2014 12:41 PM in response to David1248

It means that the server is reachable, but it's not accepting your credentials. In the Advanced settings for the server, there are several choices of authentication method, including Password and MD5 Challenge-Response. If you're using one, try the other. If the server expects you to send the password in the clear over an insecure connection, then it's incompetently managed and you shouldn't be using it at all. I suspect that might be the case, and Yosemite isn't allowing it to happen.


Also, launch the Keychain Access application and search for the server address. Delete any password items you find. The next time you try to connect, you'll be prompted for the password.

Nov 4, 2014 1:18 PM in response to David1248

David1248 wrote:


Hi Linc


Thanks for the advice. I tried both changing the authentication methods and deleting the password in the keychain access application but, unfortunately, neither seems to have worked. I still get the same error message when trying to send an e-mail.


I don't suppose that you have any other suggestions?


Many thanks

David

Try checking 'allow insecure authentication'


User uploaded file

Nov 4, 2014 1:20 PM in response to Linc Davis

Hi Linc


This is the log:


INITIATING CONNECTION Nov 04 21:18:11.170 host:relay.plus.net -- port:587 -- socket:0x0 -- thread:0x600001073d00


CONNECTED Nov 04 21:18:12.198 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:587 -- socket:0x6000006b8e40 -- thread:0x600001073d00


READ Nov 04 21:18:13.231 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:587 -- socket:0x6000006b8e40 -- thread:0x600001073d00

220 avasout01 smtp relay.plus.net


WROTE Nov 04 21:18:13.278 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:587 -- socket:0x6000006b8e40 -- thread:0x600001073d00

EHLO [192.168.0.2]


READ Nov 04 21:18:13.296 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:587 -- socket:0x6000006b8e40 -- thread:0x600001073d00

250-avasout01 hello [87.115.92.192], pleased to meet you

250-HELP

250-AUTH LOGIN PLAIN

250-SIZE 104857600

250-PIPELINING

250-8BITMIME

250 OK


Hope this helps

David

Cannot send e-mail

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