Sending in Mail doesn't work, Entourage does, Why?

Question

Sending emails in Apple's Mail doesn't work, yet Microsoft Entourage does, Why?
This is the conversation I've been having with my server tech, and they can't find the reason why I can send mail in Microsoft Entourage no problem, yet Apple Mail receives but not able to send any email what so ever..
Very frustrating.
Carl Pepper said:
2008-05-09 13:16:39 (UTC-7)
I'm having a heck of a time trying to SEND emails on the SilverSpiritHomeServices.com system.
I'm using a Mac.
I can do it in Microsoft Entourage, yet I can't do it in Mac Mail (this is the program I need to be able to use).
Receiving email it works fine, just sending it only works in Entourage.
Rackspace said:
2008-05-09 13:16:39 (UTC-7)
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Rackspace said:
2008-05-09 13:38:27 (UTC-7)
Hello,
That definitely seems odd. Since it works fine with Entourage, that would indicate the server is working properly. Additionally, I've tested the SMTP server from here (on a Mac) and am able to connect. I do not have a valid user to send email with, but I can try it if you want to provide me with the one you are trying, temporarily.
As always, if you have any other questions or concerns, please do not hesitate to contact us. Have a great day, and thanks for choosing Rackspace Managed Hosting!
Scott Wade
Linux Systems Administrator III
Rackspace Hosting ™
Toll Free 800.961.4454
International 1.210.447.4000
Carl Pepper said:
2008-05-09 14:35:36 (UTC-7)
The settings I have are:
[email protected]
mail.SilverSpiritHomeServices.com
User Name:[email protected]
Password: XXXXXX
(SMTP): pop.SilverSpiritHomeServices.com
Authentication: None
Use Secure Sockets Layer (SSL) unchecked
Carl Pepper said:
2008-05-09 15:00:15 (UTC-7)
Here is the "cheat sheet" from APPLE.COM:
"Outgoing mail server settings
Outgoing server hostname: __________________________
Such as smtp.sampleserver.com
Outgoing server port:
25 [ ] 465 [ ] 587 [ ] Other: ____
The outgoing mail server supports Secure Sockets Layer (SSL): Yes [ ] No [ ]
Outgoing server authentication type:
Password [ ] MD5 [ ] NTLM [ ] Kerberos [ ]
Outgoing server requires a username and password: Yes [ ] No [ ]
If yes, username: ___________________ password: _______________________
Can these settings be used from any Internet connection?: Yes [ ] No [ ]
If you use your ISP’s own email service (instead of a third-party such as Gmail), sometimes it may not work if you roam to another Internet access point, such as a cafe with wireless Internet. Check with your email provider that the settings they give you will work if you plan to roam."
Rackspace said:
2008-05-09 19:26:43 (UTC-7)
Hello Carl,
In your report, I notice this:
Authentication: None
You need to authenticate before you can send mail so, authentication is a must. To be thorough, I tested both SMTP and POP authentication with the credentials you specified:
$ perl -MMIME::Base64 -e 'print encode_base64("\000info\@SilverSpiritHomeServices.com\000XXXXXX")'
AGluZm9AU2lsdmVyU3Bpcml0SG9tZVNlcnZpY2VzLmNvbQBzaWx2ZXIwMA==
$ telnet mail.SilverSpiritHomeServices.com 25
Trying 72.3.249.33...
Connected to SilverSpiritHomeServices.com.
Escape character is '^]'.
220 thepepper.com ESMTP
EHLO RACKSPACE
250-thepepper.com
250-AUTH=LOGIN CRAM-MD5 PLAIN
250-AUTH LOGIN CRAM-MD5 PLAIN
250-STARTTLS
250-PIPELINING
250 8BITMIME
AUTH PLAIN AGluZm9AU2lsdmVyU3Bpcml0SG9tZVNlcnZpY2VzLmNvbQBzaWx2ZXIwMA==
235 go ahead
MAIL FROM [email protected]
250 ok
RCPT TO [email protected]
250 ok
DATA
354 go ahead
Subject: test
test 123
250 ok 1210386097 qp 32576
Now for pop:
$ nc mail.SilverSpiritHomeServices.com 110
+OK Hello there. <[email protected]>
USER [email protected]
+OK Password required.
PASS XXXXXX
+OK logged in.
All worked in both tests. Please enable authentication and get back to us.
Best Regards,
Jared Rodriguez
Rackspace Support
Carl Pepper said:
2008-05-10 15:40:13 (UTC-7)
What kind of authentication?
MD5
NTLM
GASSPI
PASSWORD
Rackspace said:
2008-05-10 18:02:07 (UTC-7)
Hello Carl,
Your server only supports CRAM-MD5 and PLAIN authentication. You will need to use plain text authentication. I have never configured mac mail so I do not know how to configure this, you may want to speak with someone a apple support if you have trouble.
Best Regards,
Jared Rodriguez
Rackspace Support
Carl Pepper said:
2008-05-10 18:46:15 (UTC-7)
Which one is plain text?
Rackspace said:
2008-05-10 20:23:43 (UTC-7)
Hello Carl,
While I am not sure, you may want to try 'PASSWORD'.
Best Regards,
Jared Rodriguez
Rackspace Support

Answer 1

I've tried mirroring the settings from Entourage. I will take another look:
ENTOURAGE
*Personal Information:*
Name: Mitch Kring
Email Address: [email protected]
*Receiving Mail:*
Account ID: [email protected]
POP Server:
Password: XXXXXX
[checked] Save password in my Mac OS keychain
(nothing in the advanced receiving options is checked)
*Sending Mail:*
SMTP Server: pop.SilverSpiritHomeServices.com
(nothing in the advanced receiving options is checked)
APPLE MAIL
Incoming Mail Server: mail.SilverSpiritHomeServices.com
User Name: [email protected]
Password: XXXXXX
Outgoing Mail Server (SMTP): pop.SilverSpiritHomeServices.com
Server Port: 465
Authentication: Password
User Name: [email protected]
Password: XXXXXX
This is all the info I can find right now..