500 Non RFC-Compliant responses received; there was a SMTP communication problem with the recipient's email server.

Error: 500 Non RFC-Compliant responses received; there was a SMTP communication problem with the recipient's email server. Please contact your system administrator.

Cause: Client copied and paste several SMTP addresses into outlook. These SMTP addresses are taken from access database, or some other database application such as Microsoft word, excel, or Client has local distribution list created on his or her outlook.
Exchange is %percent RFC compliant product.
When Client is copying and pasting SMTP addresses into outlook, outlook application seems to be putting extra space, between multiple E-mail addresses, therefore mail is bouncing.
To prevent this being happen, space must be eliminated. Based on experience this error is most likely Occurred on Outlook 2002 platform.

Solution
This is the easiest, (work around) way to get away with this error, Break the E-mail messages into smaller groups and try it again. This will prevent the space issues within outlook (Smaller groups) and message will go trough
Permanent solution would be

• Create a DL (distribution List) on AD (active Directory)
• Create External Contacts for each SMTP address,
• Add all the External Contacts to this DL as a member.
Making use Microsoft word is selected as a word editor and also
Within outlook by going
 Tools
 Options
 E-mail options
 Advance E-mail Options
 Allow Comma as address separator
 Make sure it is selected





Description: A user at our chapter received the following when sending an e-mail to her instructors. This is just two of the notifications, but they're all the same.

To check if the problem was related to her list size, she re-sent the e-mail with only 33 recipients. It still fails.

Your message did not reach some or all of the intended recipients.
Subject: Instructor Needed for Saturday 3/31 9:30-1:30pm. Please Respond! Sent: 3/30/2007 9:36 AM
The following recipient(s) could not be reached: username@wowway.com on 3/30/2007 9:36 AM

There was a SMTP communication problem with the recipient's email server. Please contact your system administrator. username@wowway.com on 3/30/2007 9:36 AM There was a SMTP communication problem with the recipient's email server. Please contact your system administrator.

Cheers
oz
System Engineer
MCSE 2003| M+| S+
MCDST | Security+

oz@MsExchange911.net
http://www.msexchange911.org/ (forums)
http://www.exchange911.org/cblog/index.php (Blog)
Http://www.consultusa.us (Blog)
http://smtp25.blogspot.com/