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 Sean Burke Lead Service Technician United Electric Supply 10 Bellecor Drive, New Castle, DE 19720 Office: 302-322-3333 Direct: 302-324-3221 Mobile: 717-629-4282 Email: sbu...@unitedelectric.com www.unitedelectric.com From: Phillip Parker <phillipipar...@hotmail.com> Sent: Tuesday, September 20, 2022 9:57 AM To: stunnel-users@stunnel.org; Sean Burke <sbu...@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<mailto:stunnel-users@stunnel.org>> Sent: Tuesday, September 20, 2022 5:08 AM To: stunnel-users@stunnel.org<mailto:stunnel-users@stunnel.org> <stunnel-users@stunnel.org<mailto: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<https://nam02.safelinks.protection.outlook.com/?url=http%3A%2F%2Focsp.pki.goog%2Fgtsr1&data=05%7C01%7Csburke%40unitedelectric.com%7C716a999675f44613631308da9b100f1b%7Cfd2267bf2ecb454d817ef263a1f00f2a%7C0%7C0%7C637992790663801242%7CUnknown%7CTWFpbGZsb3d8eyJWIjoiMC4wLjAwMDAiLCJQIjoiV2luMzIiLCJBTiI6Ik1haWwiLCJXVCI6Mn0%3D%7C1000%7C%7C%7C&sdata=4aF69Wgog0wSNYPCqj%2B3wEt6RYPozfQNg0Ap7b2GGtE%3D&reserved=0>" 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<https://nam02.safelinks.protection.outlook.com/?url=http%3A%2F%2Focsp.pki.goog%2Fgts1c3&data=05%7C01%7Csburke%40unitedelectric.com%7C716a999675f44613631308da9b100f1b%7Cfd2267bf2ecb454d817ef263a1f00f2a%7C0%7C0%7C637992790663801242%7CUnknown%7CTWFpbGZsb3d8eyJWIjoiMC4wLjAwMDAiLCJQIjoiV2luMzIiLCJBTiI6Ik1haWwiLCJXVCI6Mn0%3D%7C1000%7C%7C%7C&sdata=ssW2hy4AC3LKFPUqtx7WwDcCdZO1AgNoPYew%2FmE%2FLyo%3D&reserved=0>" 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 _______________________________________________ stunnel-users mailing list -- stunnel-users@stunnel.org<mailto:stunnel-users@stunnel.org> To unsubscribe send an email to stunnel-users-le...@stunnel.org<mailto:stunnel-users-le...@stunnel.org>
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