Unable to send e-mail from one account, but can from others in Mail.app

[luisfe123]

I'm having the weirdest problem ever. As of this morning, I cannot send e-mail form Mail.app from one of my e-mail accounts on my brand new 13" Macbook Pro.

I bought it yesterday, was sending and receiving but at some point around 11am-ish, I started having problems and now it just doesn't send. Now here comes the weird part...

1. I can send from other e-mail accounts
2. I can send from Outlook (but not Mail.app, Sparrow nor Postbox)
3. I can send when I connect to my 3G USB stick
4. I can send from my other 13" Macbook Pro (2009) using Mail.app which is on OS X Lion

The problem is my work e-mail, on this new Macbook Pro, on my install of Mail.app as of 11am this morning, it had been working over the last 12 hours before this happened.

FYI, I've done it all.

Created a new user
Repaired permissions
Deleted all the preference stuff and re-installed all acounts
Rebooted

EVERYTHING that's in these forums and nothing has worked.

Also, iPhone sends perfectly fine. On WiFi and 3G.

Here are the errors that Mail.app shows: (501 Syntactically invalid EHLO argument(s)):

READ Sep 14 23:54:59.097 [kCFStreamSocketSecurityLevelNone] -- host:mail.yucatanyes.com -- port:587 -- socket:0x1039a8760 -- thread:0x7f971dddeeb0
220 n19.c06.mtsvc.net ESMTP Exim 4.69 Wed, 14 Sep 2011 21:54:58 -0700

WROTE Sep 14 23:54:59.117 [kCFStreamSocketSecurityLevelNone] -- host:mail.yucatanyes.com -- port:587 -- socket:0x1039a8760 -- thread:0x7f971dddeeb0
EHLO unknown_e4-ce-8f-4d-57-78.gateway.2wire.net

READ Sep 14 23:54:59.240 [kCFStreamSocketSecurityLevelNone] -- host:mail.yucatanyes.com -- port:587 -- socket:0x1039a8760 -- thread:0x7f971dddeeb0
501 Syntactically invalid EHLO argument(s)

CONNECTED Sep 14 23:54:59.356 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:mail.yucatanyes.com -- port:587 -- socket:0x7f971e820870 -- thread:0x7f971dddeeb0

The hells that mean? And why does it work on Outlook and not on the other apps??!!!???!?!

 

[MisterMe]

....

READ Sep 14 23:54:59.097 [kCFStreamSocketSecurityLevelNone] -- host:mail.yucatanyes.com -- port:587 -- socket:0x1039a8760 -- thread:0x7f971dddeeb0
220 n19.c06.mtsvc.net ESMTP Exim 4.69 Wed, 14 Sep 2011 21:54:58 -0700

WROTE Sep 14 23:54:59.117 [kCFStreamSocketSecurityLevelNone] -- host:mail.yucatanyes.com -- port:587 -- socket:0x1039a8760 -- thread:0x7f971dddeeb0
EHLO unknown_e4-ce-8f-4d-57-78.gateway.2wire.net

READ Sep 14 23:54:59.240 [kCFStreamSocketSecurityLevelNone] -- host:mail.yucatanyes.com -- port:587 -- socket:0x1039a8760 -- thread:0x7f971dddeeb0
501 Syntactically invalid EHLO argument(s)

CONNECTED Sep 14 23:54:59.356 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:mail.yucatanyes.com -- port:587 -- socket:0x7f971e820870 -- thread:0x7f971dddeeb0

The hells that mean? And why does it work on Outlook and not on the other apps??!!!???!?!

Are you sure that the name of your SMTP (Outgoing Mail) server is mail.yucatanyes.com? Servers with names like that are usually POP3 (Incoming Mail) servers. I would expect your SMTP server to be named smtp.yucatanyes.com.

 

[luisfe123]

Are you sure that the name of your SMTP (Outgoing Mail) server is mail.yucatanyes.com? Servers with names like that are usually POP3 (Incoming Mail) servers. I would expect your SMTP server to be named smtp.yucatanyes.com.

100% sure, its what I have in Outlook and iPhone, which are the two that are working, oh and on the other Macbook Pro as well. The host is Mediatemple. If that makes a difference.

 

[MisterMe]

100% sure, its what I have in Outlook and iPhone, which are the two that are working, oh and on the other Macbook Pro as well. ...

The fact that you have a particular SMTP server listed on your iPhone is completely and totally irrelevant. If one SMTP server is inaccessible, then the iPhone fails through to the next one until it reaches an SMTP server that will send your message. This is unlike the behavior of Mail which gives the user the option of manually chosing a different SMTP server when the preferred server fails. My money is still on the probability that your have the wrong STMP server settings on your problematic computer.

 

[luisfe123]

The fact that you have a particular SMTP server listed on your iPhone is completely and totally irrelevant. If one SMTP server is inaccessible, then the iPhone fails through to the next one until it reaches an SMTP server that will send your message. This is unlike the behavior of Mail which gives the user the option of manually chosing a different SMTP server when the preferred server fails. My money is still on the probability that your have the wrong STMP server settings on your problematic computer.

OK, maybe I wasn't clear enough.

1. I have the exact same sever info across several computers and clients. It's not working on the new machine.

2. You're wrong about the iPhone. It ONLY send from the server I specify, it does not go through a list unless I want it to, in this case I do not have it setup that way. Same for Mail.app, I have it setup to ONLY send from that one specific server.

Also, a quick search on Google and you'll see this is a well-known problem with no solution.

 

[MisterMe]

...

2. You're wrong about the iPhone. It ONLY send from the server I specify, it does not go through a list unless I want it to, in this case I do not have it setup that way. Same for Mail.app, I have it setup to ONLY send from that one specific server.

Also, a quick search on Google and you'll see this is a well-known problem with no solution.

When you stop being snippy long enough to carefully inspect your settings, you will find that your SMTP settings are in error.

 

[applefan289]

MisterMe is correct, usually incoming mail servers have "mail." as the prefix. Outgoing mail servers has "smtp.".

For example,

The ingoing and outgoing servers for Comcast email are:

mail.comcast.net (incoming server)
smtp.comcast.net (outgoing server)