Authenticated SMTP on IIS 7.5 Issue - 501 5.7.3 Cannot decode password

vpetersen
vpetersen used Ask the Experts™
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I'm trying to setup an SMTP server using IIS 7.5 on server 2012 R2 and each time we try to connect to test emails we are receiving the following error.

501 5.7.3 Cannot decode password

Any thoughts on how to resolve this?

It's setup like this with the exception of configurion basic authentication on the outbound security and access authentication.

http://www.chrislazari.com/2011/04/iis-75-installing-smtp-service-securing.html
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Exec Consultant
Distinguished Expert 2018
Commented:
It need to be base64 encoded when testing
It’s important to note here that authentication in SMTP is done using Base64 encoded phrases.  So when I enter ‘AUTH LOGIN’ and press enter the server returns ‘VXNlcm5hbWU6’ which is Base64 for Username:.  Any and all parts of the authentication discussion will be in Base64.  I use this web site…

http://www.webpan.com/Customers/Email/base64_conversion.htm

to do Base64 encodes and decodes.  You can Google for a different method if you prefer.  Let’s do the entire authentication conversation in Base64 and then I’ll show the translated input and output.

Conversation in Base64
AUTH LOGIN
334 VXNlcm5hbWU6
YWRtaW5pc3RyYXRvcg==
334 UGFzc3dvcmQ6
cGFzc3dvcmQ=
235 2.7.0 Authentication successful

Translated back to plain text
AUTH LOGIN
334 Username:
administrator
334 Password:
password
235 2.7.0 Authentication successful
and I also suggest there is minimally basic auth
In Exchange 2007, you can open the Exchange management console, browse to Server Configuration, select Hub Transport, and then check the properties of the default receive connector....
http://www.dasblinkenlichten.com/using-telnet-to-test-authenticated-relay-in-exchange/

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Commented:
It was the decoding piece. All set thanks.

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