WhatsUp Gold - Error 501 5.5.4. in mail test

Product: Version: Platform:
WhatsUp Gold 5.0-8.0x Win2000,Win2003

Question/Problem: After an SMTP Mail test, the Debug log shows the error: 501 5.5.4. 
Here is a sample of the Debug log:
sending msg via to myemail@mailserver.com
220 NT-ESMTP Server mail.mailserver.com
HELO WhatsUp
501 5.5.4 Invalid Address

Answer/Solution: Typically, this error occurs on an Exchange Mail Server. If you telnet to the mail server on port 25 (the SMTP port) you should see the same results, i.e. telnet mail.mailserver.com 25

Even though Exchange shows this error to be an "Invalid Address", this error (5.5.4) is actually a permanent error indicating invalid command arguments. See these RFCs:

RFC1893 Enhanced Mail System Status Codes
RFC2034 SMTP Service Extension for Returning Enhanced Error Codes

This is the most probable cause:
A trailing dot or a space after the fully qualified domain name (FQDN) is interpreted as incorrect syntax, and a 501 error message is generated.

In accordance with RFC 821 and RFC 1869, Exchange 2000 and Exchange Server 5.5 SP4 do not allow trailing spaces and trailing dots. (Some SMTP hosts, such as SendMail servers, do allow trailing spaces and trailing dots.)

Right-click My Computer, go to Properties and select the Network Identification tab. Here is where you must change the Full Computer name to include the Fully Qualified Domain Name (FQDN). Go to Properties and enter the FQDN. Example: whatsup.mydomain.com

Next, reboot the machine. Then run the SMTPmail test again.

This error can also appear like this:

Connecting to ExchangeServerName
Reading initial connect greeting
R) 220 ExchangeServerName.Maildomain.COM Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Thu, 20 May 2005 09:14:07 -0500
Sending HELO command
S) HELO WhatupServer.domain.com
R) 250 ExchangeServerName.Maildomain.com Hello []
Sending MAIL FROM: command
S) MAIL FROM:"WhatsUp" <WhatsUp@Maildomain.com>
R) 501 5.5.4 Invalid arguments SMTP Error (MAIL FROM Command) 501 5.5.4 Invalid arguments

In this case you will want to use WhatsUp@Maildomain.com as the MAIL FROM address, rather than the compound email address:
"WhatsUp" <WhatsUp@Maildomain.com>

Document #:   Revision Date:
WG-20011226-DM01   05/27/05

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