I think Jerry or someone pointed this out yesterday.

# addcr | TLS_VERIFYPEER=NONE couriertls -host=64.18.4.10 -port=25
-protocol=smtp 220 Postini ESMTP 127 y5_2_3c1 ready. CA Business and Professions Code Section 17538.45 forbids use of this system for unsolicited electronic mail advertisements. STARTTLS 220 Go ahead ehlo fmp.com 250-Postini says hello back 250-8BITMIME 250 HELP mail from: <fmo...@fmp.com> 250 Ok rcpt to: <post...@blazenet.net> 250 Ok data 354 Feed me From: fmo...@fmp.com To: post...@blazenet.net Subject: testing TLS

Testing to see if Postini has their TLS problem fixed yet. . 250 Thanks quit 221 Catch you later Unexpected SSL connection shutdown.

... no problems there :-)

Can someone explain to me what's going on here? Why does this work _with_ newlines piped through addcr and yet it hangs _at the EOM marker_ without addcr. Other ESMTP commands processed in the course of the dialog are processed properly, but not in the context of the payload transfer.

Is Courier perhaps failing to send a <CR> in this particular context? Manually sending ^M^J doesn't so the same thing.

On the other hand, I've been using the same (slightly old) version of Courier for many months and had no problems at all with systems using Postini mail servers, and since they advertise secure email I'm sure that a lot of traffic has gone out to their servers from mine in an SSL context.