The reason I have been trying to use certificates is that user/pass 
authentication can be hacked relatively easily. I wanted to use STARTTLS on 
port 587 because hacking/brute forcing is much more common on the SMTP port 
25. To make it even more secure I wanted to use certificate authentication 
with STARTTLS which is an option in K-9 and postfix. This is almost totally 
unhackable unless someone manages to steal your certificates.

It seems, from an earlier post that K-9 totally refuses to use certificates 
from a self-signed CA cert or any other imported CA.

At this point I have a few options:
1 - give up on K-9
2 - root the device and hack the built-in CA cert bundle which could fail 
in an Android update
3 - just use user/pass authentication on port 587 and rely on other 
defences such as fail2ban

For the moment I'll go for 3


On Sunday, 5 April 2015 17:29:01 UTC+1, Nick Howitt wrote:
>
> Hi,
> I am trying to get K-9 to use certificates/STARTTLS to communicate with 
> and relay through my postfix mail server. I have a self-signed ca-cert and 
> have generated user certificates and keys from this. I have imported the 
> ca-cert into Android and the p12 user certificate into K-9.
>
> Using STARTTLS/port 587, every time I switch from user/pass authentication 
> to certificates I get a message from K-9:[code]Cannot connect to server. 
> (Unable to authenticate. The server does not advertise the SASL EXTERNAL 
> capability. This could be a problem with the client certificate (expired, 
> unknown certificate authority) or some other configuration 
> problem.)[/code]I have tried using a user certificate and the system 
> certificate but nothing I do changes the reply.
>
> If I try telnetting into port 587 I get:[code][root@server ~]# telnet 
> 127.0.0.1 587
> Trying 127.0.0.1...
> Connected to 127.0.0.1.
> Escape character is '^]'.
> 220 mailserver.howitts.co.uk ESMTP Postfix
> ehlo howitts.co.uk
> 250-mailserver.howitts.co.uk
> 250-PIPELINING
> 250-SIZE 51200000
> 250-ETRN
> 250-STARTTLS
> 250-AUTH LOGIN PLAIN
> 250-AUTH=LOGIN PLAIN
> 250-ENHANCEDSTATUSCODES
> 250-8BITMIME
> 250 DSN[/code]So STARTTLS is advertised. In postfix the message I get 
> is:[code]Apr  5 16:33:27 server postfix/smtpd[9162]: connect from 
> motog.howitts.co.uk[172.17.2.113]
> Apr  5 16:33:27 server postfix/smtpd[9162]: setting up TLS connection from 
> motog.howitts.co.uk[172.17.2.113]
> Apr  5 16:33:27 server postfix/smtpd[9162]: 
> motog.howitts.co.uk[172.17.2.113]: 
> Trusted: subject_CN=ourfamily, issuer=ca.server.howitts.lan, 
> fingerprint=13:45:A2:B4:94:B0:18:4A:E3:46:C0:29:29:BE:1E:27
> Apr  5 16:33:27 server postfix/smtpd[9162]: Trusted TLS connection 
> established from motog.howitts.co.uk[172.17.2.113]: TLSv1.2 with cipher 
> DHE-RSA-AES256-SHA (256/256 bits)[/code]So the connection seems to be OK at 
> the postfix end.
>
> I do sometimes get host-name mismatch warnings which I accept but then I 
> end up with the same error.
>
> Have you any idea what I am doing wrong?
>
> TIA,
>
> Nick
>
>

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