550 SMTP - SMTP Log

From your description, I understand that you encounter NDR "5.5.0 smtp;554 Transaction failed, DATA reply code" when sending mails in the Exchange 2003 environment.

Based on my research, this is a generic protocol error (SMTP error). The remote SMTP response to our EHLO with a 500 level error and the sending system will QUIT the connection and report this with NDR indicating the remote SMTP server cannot handle the protocol. (For example, if a Hotmail account is no longer active, a 550 SMTP error will occur.)

For detailed information, please check the following article:

284204 Delivery status notifications in Exchange Server and in Small Business Server
http://support.microsoft.com/default.aspx?scid=kb;EN-US;284204

Thus, the issue is mainly on the target mail server.

At this time, I want to confirm the following information.

1. Does the issue always occur when sending mails to a specific recipient or to a specific domain?

2. If you use Telnet to send a mail directly to the recipient, what is the result?

To perform the telnet test, please refer to the following article:

XFOR: Telnet to Port 25 of IMC to Test IMC Communication
http://support.microsoft.com/?id=153119

In the meantime, please collect the SMTP log for my further research. To do so:

1. In Exchange System Manager, right click the SMTP Virtual Server, and click Properties.
2. In the General tab, select "Enable Logging" and ensure the format is "W3C Extended Log File Format". Click Properties to see the path of the log file.
3. In the General Properties tab, please confirm the following settings:
- Check the option Daily
- Check the option "Use local time for file naming and rollover"
- Confirm the setting for "Log file directory" to be "C:\WINNT\System32\LogFiles"
- Check all the logging options on the Advanced tab.
4. Restart the SMTP Virtual Server.
5. Reproduce the issue and attach the log file to me.
Please send me the log file under C:\WINNT\System32\LogFiles\SMTPSVC#" (# is a number. The number for the Default SMTP Virtual Server is 1). Also, provide the sender name, recipient name, and time you send the mail for my reference.