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SSL on virtual smtp server

Posted on 2009-03-31
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Last Modified: 2012-05-06
I have one front end exchange 2003 server with 2 virtual smtp servers, virtual smtp server "A" and "B", all on the same frontend server. Both virtual smtp servers are running normally and event logs are clear of warnings or errors. (thank god)
A: virtual smtp server running on port 25
B: (NEW) virtual smtp server running with a new godaddy SSL certificate on port 465.
Everything is working normally on "A", the issue I have it's with "B". I'm using outlook to test this newly created virtual smtp server, and I'm getting this error
your outgoing smtp server does not support SSL secure connections 0X8000ccc7d. I have gone over the settings on virtual server B many times.
I have checked the box for require secure channel and require 128bit encryption and restarted smtp server service, is there anything else I'm missing, I thought this would be straigh forward. Any help is appreciated

Question:

Do I need to create a new virtual smtp server on my exchange backend server on port 465? so that the frontend server can communicate with the backend?

Thank you,
Delmiro
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Question by:Delmiroc
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Accepted Solution

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Mestha earned 500 total points
ID: 24039374
You don't need to enable the option to require SSL channel or 128bit. The fact that the certificate is there at all is enough.

If you telnet to that port and then type ehlo, is StartTLS in the command list?

Simon.

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Author Comment

by:Delmiroc
ID: 24039736
I'm using the telnet command from internet into the exchange server and get this.

220 mail.gainesville.infiniteenergy.com Microsoft ESMTP MAIL Service, Version: 6.0.3790.3959 ready at  Wed, 1 Apr 2009 10:40:11 -0400
starttls
503 5.5.2 Send hello first

Should I not have these boxes checked ? for require secure channel and 128-bit encryption?  


SMTPSSLServer.JPG
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Expert Comment

by:Mestha
ID: 24039765
You have to do exactly as I stated.

so telnet host.example.com 25
Then type

ehlo

and you get a list of commands that the server will accept.

The two options do not have to be enabled to use SSL. All they do is REQUIRE SSL.

Simon.
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Author Comment

by:Delmiroc
ID: 24039860
my virtual SSL smtp server "B" is set to on port 465, I thought we would do
telnet exchange.mydomain.com 465 ? right? anyhow I get the same results on port 25 and 465

220 myexchange.mydomain.com Microsoft ESMTP MAIL Service, Version: 6
.0.3790.3959 ready at  Wed, 1 Apr 2009 10:54:25 -0400
ehlo
250-myexchange.mydomain.com Hello []
250-TURN
250-SIZE
250-ETRN
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-VRFY
250-TLS
250-STARTTLS
250-X-EXPS GSSAPI NTLM LOGIN
250-X-EXPS=LOGIN
250-AUTH GSSAPI NTLM LOGIN
250-AUTH=LOGIN
250-X-LINK2STATE
250-XEXCH50
250 OK

what else should I check? let me know


Thank you Simon,
Delmiro
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Author Comment

by:Delmiroc
ID: 24040042
I do not know how, but I sent another test through outlook just know and it worked! I will tested again from another machine on the internet just to make sure. I have not changed any settings yet, I'm not sure why it was not working at the begining. I want to test it some more before I give it the clear.

I will let you know after I test it again.

Thank you Simon for helping.
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Author Closing Comment

by:Delmiroc
ID: 31565118
When I unselected these boxes, I got no error messages on any of the machines I tested this with. Thank you for pointing this out.

Delmiro
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Author Comment

by:Delmiroc
ID: 24107006
When I unchecked the require secure channel and 128bit encryption, i stopped getting the error message about SSL certificate 0X8000ccc7d. We are all up and running.


Thank you,
Delmiro
0

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