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MacTechTrainer, Sr. Mac Support Specialist
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I am setting up Entourage for the Mac 2008. Earthlink is involved

Customer Question

I am setting up Entourage for the Mac 2008. Earthlink is involved as a third party. The outgoing server does not recognize any of the authentication methods supported by Entourage. This is an error message 17092. What should I do?
Submitted: 8 years ago.
Category: Mac
Expert:  MacTechTrainer replied 8 years ago.
Hello, and thank you for asking your question,
I am Sr. Mac Tech Support Specialist, Terry, glad to assist you.

Could you provide me with the following information, so I can better assist you with your technical question:
• What version of Mac OS X are you using on your Mac?
(i.e. "Mac OS X 10.5.6 or Mac OS X 10.4.11, etc" -)
( If not sure how to check version of Mac OSX system- Click on Apple icon (Apple Menu) on upper left corner of screen- from the menu select "About this Mac" - you will see your version in the popup window)

• What version of Microsoft Office for Mac are you using for Entourage ? (i.e MS Office for Mac 2008 or 2004)

Your answers to the questions I have submitted, will allow me to work with more detailed information, in order to effectively answer your question.

Thanks, XXXXX XXXXX be looking forward to your reply. Thank you!


Customer: replied 8 years ago.
Mac OS 10.5.5
MS Office 2008

Note that Earthlink is involved at present but it is not essential that they remain involved, I think.
Expert:  MacTechTrainer replied 8 years ago.
Thanks for your replyCustomer

Can you provide me the incoming and outgoing mail server address that
Earthlink has provided you?

Also, I know you mentioned that you were switching from port 25 to 587 and that did not appear to work. But tell me if you would, are you able to connect to your Earthlink webmail via a web browser (i.e. Safari or Firefox ) and are able to send mail ?

I am researching this issue to determine what the causal factor for you not receiving in Entourage could be.

Thanks, XXXXX XXXXX wait for your reply.

Customer: replied 8 years ago.
The incoming address was
outgoing was
incoming port:110
outgoing port: 587
The the account name Earthlink wanted was my email address.
Note that Entourage uses "SMTP", Earthlink uses "SMTPAUTH"

I hope this helps!
Expert:  MacTechTrainer replied 8 years ago.
Thanks for your reply.

If you would I keeping your incoming mail server address at
for your outgoing mail server address, just for a trial, use the instead. Also make sure your outgoing port is changed back to 25.

Give me an update and let me know if you are able to send any test mail.

I will wait for your update, thanks!


Customer: replied 8 years ago.
I got an error message -3259 saying that the server timed out, may be down or overloaded, etc

I think that you are on the right track. While you digest this, I will go back to 587 to see if that helps.
Cordially, Ed
Expert:  MacTechTrainer replied 8 years ago.
Good now wait before you go back to port 587.

I want you to keep it at port 25, but change the outgoing server address to:

I just want to see how Entourage is acting with this SMTP addresses.

-Again, keep me posted!


Customer: replied 8 years ago.
The same timed-out occurred. This version of sprynet (POP) does not have me checking the box for security in the opttions
Customer: replied 8 years ago.
Hi Terry,
I verified what you knew--we cannot use 587 tje server rejects. We also cannot use a secure connection(SSL).

Expert:  MacTechTrainer replied 8 years ago.

Here is another process I would like you to try,
because as I have been looking into this, I have discovered that if you are not on
Earthlink's network they may block port 25

So do this:
For sake of trial once more:
• Click on the Mail icon on your Dock
When it opens up follow the prompts to set up a new email account.

• make sure to use your email address and password
• Use for your incoming email address
• Use

the Mail setup assistant is real simple to do. All you are doing is filling in the required fields with the data above and one its done, test to see if you can receive and send email.

If you are able to do so, then this would make it clear that Earthlink's SMTPAuth server, does not like Entourage. However, if the setup fails in Mac OS X Mail as well, then the issue goes back to the SMTP server address.

To guide you, here is a link for setting up Mac mail in Mac OS X Leopard, in order to
reference the images of just what you will see.

Configuring email in Mac OS X Mail for Mac OS X 10.5 Leopard

Again, we have to try this, to see if the issue is relative to the issue you are experiencing with Entourage or if the issue is with that secure server address
from Earthlink (smtpauth).

Thanks again for being so patient with me thus far Byrn463.

I am here if you have questions about this so again I will await your update.

MacTechTrainer and other Mac Specialists are ready to help you
Customer: replied 8 years ago.
Hi Terry,

Thanks for the suggestion. I wonder if this mail set up is different from the expensive .mail item that Mac has?
It is way past my bed time and I have a doctor's appointment early this morning. I will follow your advice when i can!
Expert:  MacTechTrainer replied 8 years ago.
It is Byrn463. This one is free and it is pretty much for better choice of words a
built in email client for the Mac OS X platform.

So try that and see if you achieve any different results.
One more thing, I see you have Mac OS X 10.5.5.

If I may suggest, you may want to click on the Black Apple menu icon and run your Software Updates to update to Mac OS X 10.5.8. There are alot of new updates that your system can stand to benefit from between 10.5.5 and 10.5.8.

Just a recommendation however.

Well thank you in the mean time for allowing me to assist you, I will be watching for your update tomorrow when we have some more time to work on resolving this issue for you.

Thanks for your patience, and I look forward to further assisting you then!


Customer: replied 8 years ago.
Sorry to be so late. I have now set up Mail which was indeed easy. I prepared a test message as you suggested. The response was as follows
Connection status: connection and login to server succeeded connection to server succeeded No login required
Despite the above wonderful news, the email was not sent!
the error message is:Cannot send message using server sprynet
Verify that you have addressed message correctly, Check etcetc (mentions all possibilities)
Select a different outgoing mail serveretc
What do you suggest now??
Customer: replied 8 years ago.

I got an error message from MAIL saying that sprynet did not like my password! I will fix that and get back to you.
Customer: replied 8 years ago.
Hi Terry,

I am confused! This document was labelled as having your locked answer in it, but I cannot find any answer in what has been sent.
I sent a reply to you about noon on October 4 that I have solved the problem and have sent several emails successfully. I still wanted to accept so that you would be paid for your efforts, especially introducing me to Mail emailer. However, the acceptance wording included an undefined "replenishment" clause. Please let me know what it is so that we can get closure.
Expert:  MacTechTrainer replied 8 years ago.
Hi Byrn463, good to be back to assist you again.

I was actually not ready for you to accept until the issue was resolved.

Tell me was the sprynet password XXXXX resolved?


Edited by MacTechTrainer on 10/5/2009 at 5:47 AM EST
Customer: replied 8 years ago.
Hi Terry,

Yes, it was. I had not activated my keychain because it would allow all of my passwords to be stoen if it were breached. Therefore when the keychain was asked (by a serve)r whether the password XXXXX that in the keychain, the answer was NO. That stopped the transfer of information through the server .Unlike Entourage, Mail told me that I had a password XXXXX I figured out that keychain was involved and I activated it.My next email gave a clearer error message. Mail responded by asking me to enter my user name and password XXXXX it then put into the keychain. Then when I sent a message, the server got the right answer and that was it. Thus, Mail demonstrated its superiority in this situation. I am really glad that you suggested use of Mail. You now have an extra question to ask in this situation in the future. Since the problem is solved, I am clicking " Accept". I will follow up with the management about what "replenishment" means. Good luck in your experting---a challenging activity! Customer