Re: spamd and TLS on port 25

2006-08-11 Thread Joachim Schipper
On Thu, Aug 10, 2006 at 04:06:38PM -0600, Bob Beck wrote: Also, while STARTTLS does have its merits, it's still better suited for handling MTA authentication than protecting user data - use GPG for the latter. STARTTLS opportunistically between MTA's is wonderful for making shit

Re: spamd and TLS on port 25

2006-08-11 Thread knitti
On 8/10/06, Will H. Backman [EMAIL PROTECTED] wrote: Darrin Chandler wrote: However, if the connecting party *requires* TLS then it would have a problem with spamd. Is that the trouble you're having? Yes. I'm protecting a Microsoft Exchange server with spamd on an openbsd bridge. Because

Re: spamd and TLS on port 25

2006-08-11 Thread Bob Beck
For those servicing larger networks such as universities' ResNets or campus networks, using a mandatory smarthost can be an excellent detection tool to see which users/stations need to end up in a quarantine. Granted, the largest customer base for this sort of thing are likely to be

Re: spamd and TLS on port 25

2006-08-11 Thread Bob Beck
* Bob Beck [EMAIL PROTECTED] [2006-08-11 08:23]: Speaking as someone who does this, for the truly big university there are a lot of clueless idiots... Gee, although I suppose I should use my openbsd.org address when giving such advice. Let me rephase - At most universities other

Re: spamd and TLS on port 25

2006-08-11 Thread Joachim Schipper
On Fri, Aug 11, 2006 at 03:07:01PM +0200, knitti wrote: On 8/10/06, Will H. Backman [EMAIL PROTECTED] wrote: Darrin Chandler wrote: if you just wan't to have MUAs talk to your exchange, and don't want to use STARTTLS, rdr the Exchange server to port 587 or 465 with pf. If you *want* to have a

Re: spamd and TLS on port 25

2006-08-11 Thread Joachim Schipper
On Fri, Aug 11, 2006 at 06:21:36PM +0200, Joachim Schipper wrote: On Fri, Aug 11, 2006 at 03:07:01PM +0200, knitti wrote: On 8/10/06, Will H. Backman [EMAIL PROTECTED] wrote: Darrin Chandler wrote: if you just wan't to have MUAs talk to your exchange, and don't want to use STARTTLS, rdr

Re: spamd and TLS on port 25

2006-08-11 Thread Stuart Henderson
On 2006/08/11 19:39, Joachim Schipper wrote: As Sigfred pointed out to me privately, of course, GnuPG also leaks this information. Still, STARTTLS shouldn't be used for privacy. They're complementary. STARTTLS is one way to keep sender/rcpt information a little further away from people who like

spamd and TLS on port 25

2006-08-10 Thread Will H. Backman
Am I correct in assuming that spamd and TLS on port 25 don't get along? -- Will

Re: spamd and TLS on port 25

2006-08-10 Thread Rogier Krieger
On 8/10/06, Will H. Backman [EMAIL PROTECTED] wrote: Am I correct in assuming that spamd and TLS on port 25 don't get along? Given a mail server (or MUA) that is configured to require TLS on a port it connects to, it will likely have a problem with any other end not offering TLS capability

Re: spamd and TLS on port 25

2006-08-10 Thread Darrin Chandler
On Thu, Aug 10, 2006 at 09:39:56AM -0400, Will H. Backman wrote: Am I correct in assuming that spamd and TLS on port 25 don't get along? -- Will Remember that you get *either* spamd *or* your MTA. So there's no getting along to deal with. However, if the connecting party *requires* TLS

Re: spamd and TLS on port 25

2006-08-10 Thread Will H. Backman
Darrin Chandler wrote: On Thu, Aug 10, 2006 at 09:39:56AM -0400, Will H. Backman wrote: Am I correct in assuming that spamd and TLS on port 25 don't get along? -- Will Remember that you get *either* spamd *or* your MTA. So there's no getting along to deal with. However

Re: spamd and TLS on port 25

2006-08-10 Thread Rogier Krieger
On 8/10/06, Will H. Backman [EMAIL PROTECTED] wrote: Because I require TLS and SMTP-AUTH for relaying purposes, I'm in a bind. My real problem is getting Exchange to do SMTP-TLS on a different port, so this is really a non-openbsd issue. Perhaps you'd benefit from a solution of shielding your

Re: spamd and TLS on port 25

2006-08-10 Thread Joachim Schipper
On Thu, Aug 10, 2006 at 06:13:07PM +0200, Rogier Krieger wrote: On 8/10/06, Will H. Backman [EMAIL PROTECTED] wrote: Because I require TLS and SMTP-AUTH for relaying purposes, I'm in a bind. My real problem is getting Exchange to do SMTP-TLS on a different port, so this is really a non-openbsd

Re: spamd and TLS on port 25

2006-08-10 Thread Spruell, Darren-Perot
From: [EMAIL PROTECTED] Note that at least Postfix has an independent greylisting implementation (postgrey); I'm fairly sure it's not the only one, and also fairly sure that there is a piece of code matching /milter/ and /grey/ around.

Re: spamd and TLS on port 25

2006-08-10 Thread Rogier Krieger
On 8/10/06, Joachim Schipper [EMAIL PROTECTED] wrote: Note that at least Postfix has an independent greylisting implementation True and these implementations may even be quite nice. I never felt much of a need to try it out after having setup spamd. Both are likely to work with STARTTLS;

Re: spamd and TLS on port 25

2006-08-10 Thread Joachim Schipper
On Thu, Aug 10, 2006 at 09:48:25PM +0200, Rogier Krieger wrote: On 8/10/06, Joachim Schipper [EMAIL PROTECTED] wrote: Note that at least Postfix has an independent greylisting implementation True and these implementations may even be quite nice. I never felt much of a need to try it out

Re: spamd and TLS on port 25

2006-08-10 Thread Bob Beck
Completely correct. spamd does not do TLS. It doesn't need to. since starttls will fail the mailer will fall back anyway. * Will H. Backman [EMAIL PROTECTED] [2006-08-10 07:58]: Am I correct in assuming that spamd and TLS on port 25 don't get along

Re: spamd and TLS on port 25

2006-08-10 Thread Bob Beck
Yes. I'm protecting a Microsoft Exchange server with spamd on an openbsd bridge. Because Microsoft Outlook uses Microsoft's way of having MUAs talk to MTAs, there is no problem there. I also enabled IMAPS (port 993) and SMTP-TLS (port 25) on the Exchange Server so that normal mail

Re: spamd and TLS on port 25

2006-08-10 Thread Bob Beck
Also, while STARTTLS does have its merits, it's still better suited for handling MTA authentication than protecting user data - use GPG for the latter. STARTTLS opportunistically between MTA's is wonderful for making shit like Carnivore unusable. The Government should not be able to

Re: spamd and TLS on port 25

2006-08-10 Thread Rogier Krieger
On 8/10/06, Joachim Schipper [EMAIL PROTECTED] wrote: Keep a few sanity checks (e.g. no more than X recipients for a message or no more than 100 messages a minute) snip This also helps against compromised boxes - i.e., it limits the damage. So it's generally a good idea to have some limit.