Question : 530 5.7.0 Must issue a STARTTLS command first

I have RedHat 9 and I’ve followed the ‘Gmail on Home Linux Box using Postfix and Fetchmail” instructions with what I thought was great success. (I didn’t see any errors through the process)  I’ve got the fetchmail piece working just fine, but I just can’t seem to find what I’ve done wrong with the postfix config.  I’ve search google for the error below  and got some hits but no answers that fixed my problem.  You can see the errorlog below.

Postfix Error: 530 5.7.0 Must issue a STARTTLS command first

My Network Arch
lnxsrv01.domain01.sw(RH9, Postfix) --> Cisco Firewall--> INTERNET-->smtp.google.com

Can you point me in a direction to figure out what is causing this.

Thanks for your help
Dave

 /var/log/maillog
Apr  7 14:57:54 lnxsrv01 postfix/qmgr[4584]: A5BF21C050: from=, size=428, nrcpt=1 (queue active)
Apr  7 14:57:54 lnxsrv01 postfix/smtp[4587]: initializing the client-side TLS engine
Apr  7 14:57:54 lnxsrv01 postfix/smtp[4587]: A5BF21C050: to=, relay=smtp.gmail.com[64.233.167.109], delay=10, status=bounced (host smtp.gmail.com[64.233.167.109] said: 530 5.7.0 Must issue a STARTTLS command first v50sm12660pyv (in reply to MAIL FROM command))
Apr  7 14:57:54 lnxsrv01 postfix/cleanup[4585]: D987D1C052: message-id=<20060407185754.D987D1C052@lnxsrv01.domain01.sw>
Apr  7 14:57:54 lnxsrv01 postfix/qmgr[4584]: D987D1C052: from=<>, size=2346, nrcpt=1 (queue active)
Apr  7 14:57:54 lnxsrv01 postfix/qmgr[4584]: A5BF21C050: removed
Apr  7 14:57:55 lnxsrv01 postfix/smtp[4587]: D987D1C052: to=, relay=smtp.gmail.com[64.233.167.111], delay=1, status=bounced (host smtp.gmail.com[64.233.167.111] said: 530 5.7.0 Must issue a STARTTLS command first d13sm44592pyd (in reply to MAIL FROM command))
Apr  7 14:57:55 lnxsrv01 postfix/qmgr[4584]: D987D1C052: removed

Not to confuse the issue but I was doing some trouble shooting by taking postfix out of the equation by using the openssl s_client command and I get the following error message from smtp.gmail.com . 502 5.5.1 Unrecognized command after the STARTTLS has been issued which results in SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol:s23_clnt.c:601  Does this help?


lnxsrv01:/root# openssl s_client -starttls smtp -debug -CApath /usr/share/ssl/certs/ -connect smtp.gmail.com:25
CONNECTED(00000003)
read from 08194320 [08174D80] (8192 bytes => 39 (0x27))
0000 - 32 32 30 20 2a 2a 2a 2a-2a 2a 2a 2a 2a 2a 2a 2a   220 ************
0010 - 2a 2a 2a 2a 2a 2a 2a 2a-2a 2a 2a 2a 2a 2a 2a 2a   ****************
0020 - 2a 2a 2a 2a 2a 0d 0a                                            *****..
write to 08194320 [BFFFEAA0] (21 bytes => 21 (0x15))
0000 - 45 48 4c 4f 20 73 6f 6d-65 2e 68 6f 73 74 2e 6e   EHLO some.host.n
0010 - 61 6d 65 0d 0a                                                   ame..
read from 08194320 [08174D80] (8192 bytes => 106 (0x6A))
0000 - 32 35 30 2d 6d 78 2e 67-6d 61 69 6c 2e 63 6f 6d   250-mx.gmail.com
0010 - 20 61 74 20 79 6f 75 72-20 73 65 72 76 69 63 65    at your service
0020 - 0d 0a 32 35 30 2d 53 49-5a 45 20 32 30 39 37 31   ..250-SIZE 20971
0030 - 35 32 30 0d 0a 32 35 30-2d 38 42 49 54 4d 49 4d   520..250-8BITMIM
0040 - 45 0d 0a 32 35 30 2d 58-58 58 58 58 58 58 41 0d   E..250-XXXXXXXA.
0050 - 0a 32 35 30 20 45 4e 48-41 4e 43 45 44 53 54 41   .250 ENHANCEDSTA
0060 - 54 55 53 43 4f 44 45 53-0d 0a                               TUSCODES..
write to 08194320 [BFFFEAA0] (10 bytes => 10 (0xA))
0000 - 53 54 41 52 54 54 4c 53-0d 0a                               STARTTLS..
read from 08194320 [08172D78] (8192 bytes => 47 (0x2F))
0000 - 35 30 32 20 35 2e 35 2e-31 20 55 6e 72 65 63 6f    502 5.5.1 Unreco
0010 - 67 6e 69 7a 65 64 20 63-6f 6d 6d 61 6e 64 20 32    gnized command 2
0020 - 34 73 6d 33 32 38 30 30-39 31 6e 7a 6e 0d 0a       4sm3280091nzn..
write to 08194320 [081AF8D0] (148 bytes => 148 (0x94))
0000 - 80 92 01 03 01 00 69 00-00 00 20 00 00 39 00 00   ......i... ..9..
0010 - 38 00 00 35 00 00 16 00-00 13 00 00 0a 07 00 c0   8..5............
0020 - 00 00 33 00 00 32 00 00-2f 00 00 07 05 00 80 03   ..3..2../.......
0030 - 00 80 00 00 66 00 00 05-00 00 04 01 00 80 08 00   ....f...........
0040 - 80 00 00 63 00 00 62 00-00 61 00 00 15 00 00 12   ...c..b..a......
0050 - 00 00 09 06 00 40 00 00-65 00 00 64 00 00 60 00   [email protected]..`.
0060 - 00 14 00 00 11 00 00 08-00 00 06 04 00 80 00 00   ................
0070 - 03 02 00 80 b0 c3 5e 1d-87 5a ea 1c 64 d5 ef 94   ......^..Z..d...
0080 - 17 c0 9b b0 84 cc a5 68-75 2f 18 7e 76 1d ea 3f   .......hu/.~v..?
0090 - 2d dc 1c c4                                       -...
read from 08194320 [081B4E30] (7 bytes => 7 (0x7))
0000 - 35 30 32 20 35 2e 35                              502 5.5
11686:error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol:s23_clnt.c:601:

Answer : 530 5.7.0 Must issue a STARTTLS command first

first lets turn up the logging for postfix.  In the master.cf file one of the first lines (uncommented that is) you should see is something like this:
smtp  inet - - - - smtpd
add to this line so that the end says "smtpd -v -v" instead of just "smtpd"

this will turn on verbose logging so that you will be able to see the entire smtp communication in the logs.

WARNING: if you server has a lot of traffic than do not have this active for long or your logs will really balloon out of control.
After you get that changed restart postfix (not just a reload; my personal preference to ensure the entire postfix daemon is running correctly)
then post the relevant logs.

you might want to post a sanitized copy of the main.cf as well.  i don't want to speculate aon what I think it is until I get a little more information.