I am not sure what has changed, but I tested this setup last week in order to continue troubleshooting this, and the emails went through. Stunnel has been working well with the account setup to use an app password now. Just an FYI to anyone
dealing with this.
Sean
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From: Phillip Parker <phillipiparker@hotmail.com>
Sent: Tuesday, September 20, 2022 9:57 AM
To: stunnel-users@stunnel.org; Sean Burke <Sburke@unitedelectric.com>
Subject: [EXTERNAL]Re: [stunnel-users] error:0A000126:SSL routines::unexpected eof while reading
Looking forward to see if someone has an answer. I am encountering the same problem using hotmail. In my case it appears that stunnel is connecting with the outlook server but I never receive an
email back.
From: sburke--- via stunnel-users <stunnel-users@stunnel.org>
Sent: Tuesday, September 20, 2022 5:08 AM
To: stunnel-users@stunnel.org <stunnel-users@stunnel.org>
Subject: [stunnel-users] error:0A000126:SSL routines::unexpected eof while reading
Hello,
I am trying to get a system notification email back up and running after google disabled the "use less secure apps" functionality in the Gmail platform.
I have set up the Gmail account to use an app password which I assigned to the system that was sending emails before this change. It appears the system is now connecting to Stunnel running on a windows 10 machine and Stunnel is making the connection with the
Gmail server again, but no email actually gets sent out.
I am running Stunnel 5.66
Here is the configuration currently:
[gmail-smtp]
client = yes
accept = 25
connect = smtp.gmail.com:465
verifyChain = yes
CAfile = ca-certs.pem
checkHost = smtp.Gmail.com
OCSPaia = yes
Here is a copy of the log file:
2022.09.20 07:40:49 LOG5[0]: Service [gmail-smtp] accepted connection from 192.168.100.200:56399
2022.09.20 07:40:49 LOG5[0]: s_connect: connected 74.125.138.109:465
2022.09.20 07:40:49 LOG5[0]: Service [gmail-smtp] connected remote server from 172.16.4.220:60367
2022.09.20 07:40:49 LOG5[0]: OCSP: Connecting the AIA responder "http://ocsp.pki.goog/gtsr1"
2022.09.20 07:40:50 LOG5[0]: s_connect: connected 142.251.40.67:80
2022.09.20 07:40:50 LOG5[0]: OCSP: Certificate accepted
2022.09.20 07:40:50 LOG5[0]: OCSP: Connecting the AIA responder "http://ocsp.pki.goog/gts1c3"
2022.09.20 07:40:50 LOG5[0]: s_connect: connected 142.251.40.67:80
2022.09.20 07:40:50 LOG5[0]: OCSP: Certificate accepted
2022.09.20 07:40:50 LOG5[0]: Certificate accepted at depth=0: CN=smtp.gmail.com
2022.09.20 07:40:51 LOG3[0]: SSL_read: ssl/record/rec_layer_s3.c:308: error:0A000126:SSL routines::unexpected eof while reading
2022.09.20 07:40:51 LOG5[0]: Connection reset: 92 byte(s) sent to TLS, 620 byte(s) sent to socket
Is this something I can remedy from the configuration, or is this something that requires modification on the email server side?
Thank you
sean
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