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I'm using an older e-mail client (Edit: Eudora 7.1.0.9 on Windows) which seems unable to send e-mail through Gmail's SMTP server, even after lowering the security per this article.
So I tried adding stunnel between the e-mail client and Gmail, but it still fails with the same error message telling me to read the article at the following URL: https://support.google.com/mail/answer/14257
Here's the stunnel.conf file:
output = stunnel.log
debug = debug
engine = capi
cert = stunnel.pem
options = NO_SSLv2
[gmail-smtp]
client = yes
accept = 127.0.0.1:25
connect = smtp.gmail.com:465
Here's the log from stunnel:
2014.09.12 13:29:09 LOG7[6896]: Service [gmail-smtp] accepted (FD=440) from 127.0.0.1:56142
2014.09.12 13:29:09 LOG7[6896]: Creating a new thread
2014.09.12 13:29:09 LOG7[6896]: New thread created
2014.09.12 13:29:09 LOG7[6516]: Service [gmail-smtp] started
2014.09.12 13:29:09 LOG5[6516]: Service [gmail-smtp] accepted connection from 127.0.0.1:56142
2014.09.12 13:29:09 LOG6[6516]: s_connect: connecting 173.194.66.109:465
2014.09.12 13:29:09 LOG7[6516]: s_connect: s_poll_wait 173.194.66.109:465: waiting 10 seconds
2014.09.12 13:29:09 LOG5[6516]: s_connect: connected 173.194.66.109:465
2014.09.12 13:29:09 LOG5[6516]: Service [gmail-smtp] connected remote server from 192.168.0.12:56143
2014.09.12 13:29:09 LOG7[6516]: Remote socket (FD=524) initialized
2014.09.12 13:29:09 LOG6[6516]: SNI: sending servername: smtp.gmail.com
2014.09.12 13:29:09 LOG7[6516]: SSL state (connect): before/connect initialization
2014.09.12 13:29:09 LOG7[6516]: SSL state (connect): SSLv3 write client hello A
2014.09.12 13:29:09 LOG7[6516]: SSL state (connect): SSLv3 read server hello A
2014.09.12 13:29:09 LOG7[6516]: SSL state (connect): SSLv3 read finished A
2014.09.12 13:29:09 LOG7[6516]: SSL state (connect): SSLv3 write change cipher spec A
2014.09.12 13:29:09 LOG7[6516]: SSL state (connect): SSLv3 write finished A
2014.09.12 13:29:09 LOG7[6516]: SSL state (connect): SSLv3 flush data
2014.09.12 13:29:09 LOG7[6516]: 1 items in the session cache
2014.09.12 13:29:09 LOG7[6516]: 4 client connects (SSL_connect())
2014.09.12 13:29:09 LOG7[6516]: 4 client connects that finished
2014.09.12 13:29:09 LOG7[6516]: 0 client renegotiations requested
2014.09.12 13:29:09 LOG7[6516]: 0 server connects (SSL_accept())
2014.09.12 13:29:09 LOG7[6516]: 0 server connects that finished
2014.09.12 13:29:09 LOG7[6516]: 0 server renegotiations requested
2014.09.12 13:29:09 LOG7[6516]: 3 session cache hits
2014.09.12 13:29:09 LOG7[6516]: 0 external session cache hits
2014.09.12 13:29:09 LOG7[6516]: 0 session cache misses
2014.09.12 13:29:09 LOG7[6516]: 0 session cache timeouts
2014.09.12 13:29:09 LOG6[6516]: SSL connected: previous session reused
2014.09.12 13:29:13 LOG6[6516]: SSL socket closed (SSL_read)
2014.09.12 13:29:13 LOG7[6516]: Sent socket write shutdown
2014.09.12 13:29:13 LOG5[6516]: Connection closed: 100 byte(s) sent to SSL, 702 byte(s) sent to socket
2014.09.12 13:29:13 LOG7[6516]: Remote socket (FD=524) closed
2014.09.12 13:29:13 LOG7[6516]: Local socket (FD=440) closed
2014.09.12 13:29:13 LOG7[6516]: Service [gmail-smtp] finished (0 left)
2014.09.12 13:29:13 LOG7[6516]: str_stats: 3 block(s), 4294963962 data byte(s), 150 control byte(s)
2014.09.12 13:29:13 LOG7[6516]: str_stats: 20 byte(s) at ..\src\network.c:413
2014.09.12 13:29:13 LOG7[6516]: str_stats: 20 byte(s) at ..\src\network.c:412
2014.09.12 13:29:13 LOG7[6516]: str_stats: 20 byte(s) at ..\src\network.c:411
Any hint from stunnel or SSL experts?
Thank you.
What is the email client? – DavidPostill – 2014-09-12T11:36:41.957
It's Eudora 7.1.0.9 – OverTheRainbow – 2014-09-12T11:38:48.160
Have you tried the instructions in How to Access Gmail with Eudora?
– DavidPostill – 2014-09-12T11:41:58.450The stunnel output gives no useful information. Could you provide a packet dump and upload to cloudshark.org or provide a link to the full pcap file. – Steffen Ullrich – 2014-09-12T11:44:57.710
Thanks for the link, but I will only use Gmail to send e-mail (SMTP), not receive any (POP3).
I don't know how to enable packet dump/pcap in Windows, but will search and post back. – OverTheRainbow – 2014-09-12T16:38:56.197