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

I have followed amazon's guide here:

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.


Any help is appreciated

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The root bounce: – vibeweb Nov 21 '13 at 13:52

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

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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?

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Hi, OpenSSL is installed correctly yes – vibeweb Nov 25 '13 at 8:15

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