SMTP relay security

pearsont74 · Post by **pearsont74** » Mon Jul 24, 2006 1:28 pm

I have done a few quick tests and I am having issue with this SMTP Relay.
The only way i have been to able to get it to work correctly is to use the open relay.
Here is what I am on and the steps i have taken.
I have a hosted dedicated server that is not on my domain but does have the correct DNS entries (as far as I can tell from the diag i have run).
I am running ME Pro 2.11 the is registred.
Most everyone is using Outlook 03. This is set up with the correct mail server name and have checked that they use authincation on the smpt (i am unsure if i need to use the log onto the pop before sending mail or the option that say it is the same as pop)

When i go on the relay setting and check the top option to use relay authincation and make sure the advance is set to ME log on accounts i get an error msg when senidn a test.
503 This mail server requires authentication when attempting to send to a non-local e-mail address. Please check your mail client settings or contact your administrator to verify that the domain or address is defined for this server

I do not understand whats wrong and i need to know what im missing to cause this.

Post by **MailEnable-Ben** » Tue Jul 25, 2006 6:32 am

Try these;

http://www.mailenable.com/kb/Content/Ar ... D=me020135

http://www.mailenable.com/kb/viewarticl ... 020001.htm

pearsont74 · Post by **pearsont74** » Tue Jul 25, 2006 2:46 pm

ihave seen these and read them....
All my clients have the setting checked to use authenication on smtp and some email messages get through and others dont. I do not have time to troubleshoot this...i'm getting very frusterated with ME and getting close to looking at MS exchange instead.

laurenb · Post by **laurenb** » Tue Jul 25, 2006 5:09 pm

I've read the articles as well and have EXACTLY the same situation. I am also using a dedicated, hosted server. Everything is set according to the instructions and I have tested every different setting for Outlook. NOTHING works. HELP!

pearsont74 · Post by **pearsont74** » Tue Jul 25, 2006 5:29 pm

laurenb wrote:I've read the articles as well and have EXACTLY the same situation. I am also using a dedicated, hosted server. Everything is set according to the instructions and I have tested every different setting for Outlook. NOTHING works. HELP!

not sure if this is the reason but i ran a dns report and fixed some errors and will test later on this.

go here and test ur dns and see if anything fials and try to fix it: http://www.dnsreport.com/

Post by **MailEnable-Ben** » Wed Jul 26, 2006 1:38 am

Thanks for that it was basically going to be my next point. The relay, client and configuration settings within MailEnable that cause this error are quite simple.

If you still get the error after this then you are most likely experiencing something harder to diagnose. The first things I would check are DNS settings as pearson74 correctly did or find out why the server you are hitting with your client does not contain the mailbox or at the least thinks it does not contain.

If you DNS looks fine still then see if the entry/mailbox exists in the Program Files\MailEnable\Config\address-map.tab file.

If you still cannot find the problem then please submit a support request via the MailEnable web site.

As for trying exchange feel free but by the sounds of it you will have the same difficulty there.

laurenb · Post by **laurenb** » Wed Jul 26, 2006 12:08 pm

The problem is authenticating for SMTP relay. I can RECEIVE messages in Outlook just fine but I can't SEND. It seems that the problem may be that it's on another domain than our local one. It's a hosted server.

I'm also contacting my hosting company to check the DNS issue I found. Hopefully that will solve the problem.

TrialUserXP · Post by **TrialUserXP** » Thu Jul 27, 2006 1:46 am

did u try username@postofficename as yr username for smtp authentication?

pearsont74 · Post by **pearsont74** » Thu Jul 27, 2006 3:21 pm

TrialUserXP wrote:did u try username@postofficename as yr username for smtp authentication?

it is set to use the same as the pop server which tests fine...and yes all teh outlooks are set to use the usename with the full email address: name@postoffice

pearsont74 · Post by **pearsont74** » Mon Jul 31, 2006 1:11 pm

ok...last night i set the relay to use the EM autchincation and not open and did a few test....so far things looked good till i got int he end users started emailing....no one leaves their PC up over the weekend so it was from bootup, open outlook and some emails instantly got teh 503 message....this is annoying..i dont have time to troubleshoot this
all my diago pass without and dns checks good.
i did however encrypt password to help keep spoofer from using our accounts.

Post by **MailEnable-Ben** » Wed Aug 02, 2006 2:10 am

If you want a faster resolution submit a request via the support page on the MailEnable web site. Send through remote desktop details via this secure link also, then someone can log in and find out what the problem with your configuration is.

https://www.mailenablecorp.com/secure/details.asp

pearsont74 · Post by **pearsont74** » Thu Oct 26, 2006 1:03 pm

Just curious...in the SMTP properties...does the option under security "senders from local domains must authenticate to send email' have to be checked in order to have the relay option allow relay for authenicated senders to work correctly???

anyways...update on this, i upgraded to the lastest an greatest MEPro and went in and tried the relay again and started gettin complaints that users cant send...gets the "503 This mail server requires authentication when attempting to send to a non-local e-mail address. Please check your mail client settings or contact your administrator to verify that the domain or address is defined for this server"
I double checked to make sure their outlook was set correctly.

Post by **MailEnable-Ben** » Fri Oct 27, 2006 4:23 am

No it does not.

ezwpp · Post by **ezwpp** » Sat Oct 28, 2006 4:02 pm

I thought I had my outlook set up correctly also, but didn't, I'm not saying you don't Please humor or bear with me on the correct setup that you have. In Outlook do you have the a check mark in "Log on using secure password authentication (SPA)" on the account setup page because if you do it will not work.
Click More Settings tab or Properties and then click Outgoing Server tab and make sure you have a check mark in the "My outgoing (SMTP) Server requires Authentication. Now click the "Log on Using" and place FULL email address and password in fields, now click on "Remember Password" Also check the box below that "Log on using secure password authentication (SPA)" DO NOT click on the box if present below that "Log on the incoming mail server before sending mail"
Thanks for bearing with me, and I hope I shed some light on this issue, if not maybe someone else can be helped by this.

pearsont74 · Post by **pearsont74** » Mon Oct 30, 2006 1:53 pm

ezwpp wrote:I thought I had my outlook set up correctly also, but didn't, I'm not saying you don't Please humor or bear with me on the correct setup that you have. In Outlook do you have the a check mark in "Log on using secure password authentication (SPA)" on the account setup page because if you do it will not work.
Click More Settings tab or Properties and then click Outgoing Server tab and make sure you have a check mark in the "My outgoing (SMTP) Server requires Authentication. Now click the "Log on Using" and place FULL email address and password in fields, now click on "Remember Password" Also check the box below that "Log on using secure password authentication (SPA)" DO NOT click on the box if present below that "Log on the incoming mail server before sending mail"
Thanks for bearing with me, and I hope I shed some light on this issue, if not maybe someone else can be helped by this.

great....ill try that...i didnt see any documentation about checking that. Does the smtp relay have to be checked to use ME authincation before checking this? I did a quick test and it wouldnt allow me to connect to the pop server. Ill test it most after hours...and check that EM relay box and then the SPA option as stated above. also you know in outlook 2003 theres 2 places for SPA...on the main account page and then also under the outgoing mail page.
Finally someone giving decent info...thank you (even if it doesnt work but i'd like to think it would.

)

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