I have been using Exchange 2007 with postfix mail gateway for almost 3 years 
now; both outbound and inbound are encrypted and have had minimal issues (due 
to my own stupidity) with communications.  I posted a few years ago when I was 
running Exchange 2003 which did not do encryption properly and you had to make 
mods to postfix to make it work right.  The following works for me (note I use 
same root CA for both postfix and Exchange 2007):

smtpd_use_tls = yes
smtp_use_tls = yes
smtp_tls_note_starttls_offer = yes
smtpd_tls_auth_only = no
smtp_tls_security_level = may
smtpd_tls_key_file = /etc/postfix/ssl/server.key
smtpd_tls_cert_file = /etc/postfix/ssl/server_selfsign.crt
smtpd_tls_CAfile = /etc/postfix/ssl/server_selfsign.crt
smtp_tls_CAfile = /etc/postfix/exchange.pem
smtp_tls_policy_maps = hash:/etc/postfix/tls_policy
smtpd_tls_mandatory_ciphers = high
smtpd_tls_loglevel = 14
smtpd_tls_received_header = yes
smtpd_tls_session_cache_timeout = 3600s
tls_random_source = dev:/dev/urandom
smtpd_tls_session_cache_database = sdbm:/etc/postfix/smtpd_scache
smtpd_tls_session_cache_database = btree:/var/lib/postfix/smtpd_scache

-----Original Message-----
From: owner-postfix-us...@postfix.org [mailto:owner-postfix-us...@postfix.org] 
On Behalf Of Victor Duchovni
Sent: Friday, August 21, 2009 2:28 PM
To: postfix-users@postfix.org
Subject: Re: MS-Exchange fails when receiving postfix has smtpd_enforce_tls=true

On Fri, Aug 21, 2009 at 10:54:49PM +0200, gmx wrote:

> Hi Victor,
> 
> In http://marc.info/?l=postfix-users&m=116171112425304&w=2 you described
> problems with ciphers when connecting from MS-Exchange to postfix. Has there
> been any improvement in the last almost-3 years?

AFAIK, the problem is resolved in Vista at the latest SP levels.  XP,
and perhaps Server 2003 are AFAIK still broken for ciphers other than RC4.

> In a similar vein, we are having problems to mandatorily send TLS encrypted
> mails from an MS-Exchange to a postfix.
> 
> We always get a 
> 
> <<530 5.0.0 Permanent message delivery failure - 530 5.7.0 Must issue a
> STARTTLS command first (in reply to end of DATA command))>>

This is logged by the Postfix SMTP client, when sending mail out, not
the SMTP server. Perhaps you are inadvertantly enforcing TLS post
content filter, ...

> Postfix 2.4.6 settings are
> smtpd_tls_cipherlist = MEDIUM:HIGH:!MD5:!aNULL

This parameter is not used in 2.3 or later, and this setting is not wise
in any case.

> smtpd_tls_mandatory_ciphers=medium
> smtpd_tls_exclude_ciphers=aNULL

This is fine.

> smtpd_enforce_tls = yes

Ignored.

> smtpd_tls_security_level=encrypt

This makes the former unnecessary.

> When we turn off the last 2, it all works fine, and the received header
> still claims that the message had 
> 
> >          (using TLSv1 with cipher RC4-MD5 (128/128 bits))
> >          (No client certificate requested)
> >          (Authenticated sender: umbricht...@sig.privasphere.com)
> 
> but AFAIK without the last 2, we cannot prevent sending-side omissions of
> TLS from the receiving side and we would really like to ensure that as
> receivers.

Sure looks like you are having trouble forwarding mail received from
Exchange, not receiving from Exchange.

-- 
        Viktor.

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