Issues using Amazon SES as relay with sendmail [530 Must issue a STARTTLS command first]

Question

I'm trying to get our old rhel3 servers relaying out with sendmail 8.13.1

I have followed amazon's guide here: http://docs.aws.amazon.com/ses/latest/DeveloperGuide/sendmail.html

But it seems the server does not authenticate correctly with amazon, the bounced back email states a "<<< 530 Must issue a STARTTLS command first" - as in something is not happing in the correct order.

My sendmail.mc: http://pastebin.com/k0Y1s6pZ

Any help is appreciated

The root bounce: http://pastebin.com/t22G4F69 – vibeweb Nov 21 '13 at 13:52 — vibeweb, Nov 21 '13 at 13:52

score 1 · Answer 1 · answered Dec 03 '13 at 09:44

1

The issue was resoved after we discovered that the EDGE Cisco ASA did some packet inspection on the SMTP steam, and removing the STARTTLS completely

answered Dec 03 '13 at 09:44

vibeweb

11
3

score 0 · Answer 2 · answered Nov 24 '13 at 17:40

0

It seems that your sendmail must issue STARTTLS (convert connection into encrypted connection) before issuing AUTH.

AFAIR sendmail tries to use STARTTLS by default. Have you installed openssl package/rpm on your host?

answered Nov 24 '13 at 17:40

AnFi

5,883
1
12
26

Hi, OpenSSL is installed correctly yes – vibeweb Nov 25 '13 at 08:15

Issues using Amazon SES as relay with sendmail [530 Must issue a STARTTLS command first]

2 Answers2