Thanks Davide,

However, could you confirm that I've got the setup basically correct? I've also 
tried changing the routing to go through stunnel, without TLS, which I know 
works directly from my email client, but I couldn't get that to work either:

smtpfwd.tab -

"secure.net"    "localhost:2525"

\userauth\smtp\localhost.tab -

"PLAIN" "myusername" "437687234219932"
or
"LOGIN" "myusername" "437687234219932"

Is my understanding of the use of the userauth\smtp\xxxx.tab file correct? 

On 3 Mar 2010, at 23:18, Davide Libenzi wrote:

> On Wed, 3 Mar 2010, Colin Johnston wrote:
> 
>> I've just downloaded xmail (windows) and I'm trying to set it up to fulfil 
>> our specific requirements.
>> We only need xmail to relay all mail it receives from local sources, 
>> choosing the destination smtp server depending on the destination domain. 
>> Local traffic should go via our internal smtp gateway (anonymous, 
>> unencrypted) (say internal.net), but external traffic should go via a 
>> TLS-encrypted smtp server using a specified username and password (say 
>> secure.net). Ideally we'd also like to replace the message body of any email 
>> going to an external destination other than secure.net with a simple link or 
>> general text.
>> 
>> To make this work I've set up anonymous relaying from the local network 
>> (works OK) and also added entries to the smtpfwd.tab file (this doesn't 
>> cover other external addresses but I want to get the basics working first):
>> 
>> "internal.net" "smtp.internal.net"
>> "secure.net" "smtp.secure.net:587,NeedTLS=1"
>> 
>> However I don't think I can put the authentication details in this file, so 
>> I've created another file \userauth\smtp\smtp.secure.net.tab with the 
>> following entries:
>> 
>> "LOGIN" "myusername" "437687234219932"
>> 
>> (with tabs beween quoted entries)
>> 
>> Note that I've also tried replacing "LOGIN" with "PLAIN". The password has 
>> been created by XMCrypt.
>> 
>> Sending email destined for internal.net addresses is relayed correctly, but 
>> mail sent to secure.net addresses does not get there. The usual error is 
>> Client not authenticated, but trying different settings I've also had 
>> authorization method errors. I've checked the password and can send mail via 
>> secure.net if I use my mail client (unencrypted) routing through a local 
>> stunnel daemon rather than xmail.
>> 
>> Have I got the settings corrent? What else can I do to make this work?
> 
> There are two ways to talk TLS in the SMTP world.  SMTPS, which is TLS 
> since time zero, or STARTTLS which starts in clear and then uses STARTTLS 
> to switch to TLS.
> I noticed that XMail at the moment does not support the former, which I 
> will add for 1.28.
> 
> 
> 
> - Davide
> 
> 
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