Problem Sending Mail using SMTP through Proxy

Asked by Mark Appier on 2009-06-07

When attempting to send an email from Jaunty's Evolution using SMTP through a proxy server (Squid Client), I receive the following error:

"Unable to authenticate to SMTP Server.
Bad authentication response from server."

The computer is in a small, parochial school chemistry lab. There are two other machines in the same room on the same network using Debian Lenny Evolution 2.22.3.1 and the other using Ubuntu Intrepid Evolution 2.24.3. To the best of my knowledge, I have them set up identically, and they are working perfectly. Also strange, I have another computer with Ubuntu Jaunty at home using Evolution 2.26.1 without going through the proxy, it works perfectly as well.

Incoming email works properly on all of the machines.

Can someone with a bit more experience tell me, "Have I found a bug?"

Thanks,

Mark

Question information

Language:
English Edit question
Status:
Open
For:
Ubuntu evolution Edit question
Assignee:
No assignee Edit question
Last query:
2009-07-19
Last reply:
2009-07-18

Does the proxy use a username / password? If so you will need to add those details to the connection too.

Mark Appier (appier) said : #2

Yes, it does use a username / password? I double-checked this morning to make sure it was set up properly, and it is set up in the same manner as the working installation of Evolution on the Intrepid and Lenny machines. I have no problems receiving messages on the Jaunty installation of Evolution, just sending them.

Thank you for your reply.

Mark

Mark Appier (appier) said : #3

Sorry, Grammar Edit for Puctuation:

Yes, it does use a username / password. I double-checked this morning to make sure it was set up properly, and it is set up in the same manner as the working installation of Evolution on the Intrepid and Lenny machines. I have no problems receiving messages on the Jaunty installation of Evolution, just sending them.

Thank you for your reply.

Mark

midnightflash (midnightflash) said : #4

Which kind of proxy is this? University, or at work, or did you setup a proxy-server yourself for fun?
Usually proxys are used to break such things like sending mails or doing ICQ or whatever. (Initially the use of proxys were to save bandwidth and to speed up internet-connections... see what bad people are doing from something good? E=MC² ~ Atomic-Bomb ;-) )

Mark Appier (appier) said : #5

The proxy used is the Squid Client. It is at a small parochial high school where I am the high school sciences teacher. The server being accessed is the school's email server which is a Microsoft Exchange Server 2003 being access via IMAP with outgoing mail using SMTP. The account being accessed is my official school-related account. The Network Administrator's solution to the problem was to not require internal traffic to our Exchange server to go through the proxy. After that, it worked just fine. If you would like more detailed information regarding the system, I do have full access to the desktops mentioned above. Thank you for your response!

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