Hi, It seems I've been bitten by one of the bugs that exist in sendmail 8.13.4 that ships with obsd3.9 This particular bug was fixed in 8.13.5: When a server responds with 421 to the STARTTLS command then treat it as a temporary error, not as protocol error. Problem noted by Andrey J. Melnikoff. I know that this won't be officially supported by the obsd developers, but is the idea to update just the sendmail component to -current (sendmail 8.13.8) on 3.9-stable a reasonable one, or am I being completely stupid.
I've got a lot of boxes on obsd 3.9-stable, and although I will update them to 4.0 when it comes out, I was hoping to fix this sendmail problem in a quicker way than updating them all to 4.0-beta, then updating them all again to 4.0 when it comes out. ( as I am still a newbie, I prefer -stable to -current on production boxes ) Thanks, Craig.