send invite email failed (openssl)

[dercaptainbc]

Hello,

I'm running outline in version 0.74.0 as a docker container on a Debian 11. Since the update from 0.68.1 to current version. The sending of the invite mail fails.

To Reproduce
Steps to reproduce the behavior:

1. Go to login screen
2. Click on Continue with Email
3. Type in mail and press Sign In
4. No Error in Frontend, but following inside the docker container

{"error":"All promises were rejected","level":"error","message":"Error processing task in ValidateSSOAccessTask","stack":"AggregateError: All promises were rejected"}
{"label":"worker","level":"info","message":"EmailTask running","props":{"client":"web","teamUrl":"https://wiki.example.de","to":"me@example.com","token":"[Filtered]"},"templateName":"SigninEmail"}
{"label":"email","level":"info","message":"Sending email \"Magic signin link\" to me@example.com"}
{"error":"988B95D56F7F0000:error:0A00010B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:354:\n","level":"error","message":"Error sending email to me@example.com","stack":"Error: 988B95D56F7F0000:error:0A00010B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:354:\n"}
{"error":"988B95D56F7F0000:error:0A00010B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:354:\n","level":"error","message":"Error processing task in EmailTask","stack":"Error: 988B95D56F7F0000:error:0A00010B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:354:\n"}
{"label":"worker","level":"info","message":"EmailTask running","props":{"client":"web","teamUrl":"https://wiki.example.de","to":"me@example.com","token":"[Filtered]"},"templateName":"SigninEmail"}
{"label":"email","level":"info","message":"Sending email \"Magic signin link\" to me@example.com"}
{"error":"988B95D56F7F0000:error:0A00010B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:354:\n","level":"error","message":"Error sending email to me@example.com","stack":"Error: 988B95D56F7F0000:error:0A00010B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:354:\n"}
{"error":"988B95D56F7F0000:error:0A00010B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:354:\n","level":"error","message":"Error processing task in EmailTask","stack":"Error: 988B95D56F7F0000:error:0A00010B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:354:\n"}

mail address and domain are anonymised

[linear[bot]]

OLN-207 send invite email failed (openssl)

[infinitr0us]

Yep, I got an exact same problem here... I used the Gmail setup and got the same OpenSSL error in logs