Unable to send out invites

[martinl88]

While trying to send out invites, UI says "invites sent" but in reality nothing seems to happen. In docker logs I can see this:

outline     | (node:59) UnhandledPromiseRejectionWarning: Error: 140097387232584:error:1408F10B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:332:
outline     |
outline     | (node:59) UnhandledPromiseRejectionWarning: Unhandled promise rejection. This error originated either by throwing inside of an async function without a catch block, or by rejecting a promise which was not handled with .catch(). To terminate the node process on unhandled promise rejection, use the CLI flag `--unhandled-rejections=strict` (see https://nodejs.org/api/cli.html#cli_unhandled_rejections_mode). (rejection id: 3)

I've tried with two different SMTP servers, with and without auth.

To Reproduce
Steps to reproduce the behavior:

1. Click on 'Invite people...'
2. Fill out the form
3. Click on 'Send invites'

Expected behavior
Invites should be sent out

Outline (please complete the following information):

• Install: self hosted
• Version: v0.57.0
• Docker image: outlinewiki/outline:latest

[tommoor]

Try setting the environment variable SMTP_TLS_CIPHERS=SSLv3

[soulteary]

Try setting the environment variable SMTP_TLS_CIPHERS=SSLv3

Perhaps supporting the use of the API Email service can solve many such problems.

For example, eg. mailgun, or a service unique to each user area.

[tommoor]

If there is a bug to fix here it would be that it would be nice to capture this specific error and display a friendly error message to modify the configuration.

[martinl88]

Try setting the environment variable SMTP_TLS_CIPHERS=SSLv3

Sadly it didn't help. The same error is being spat out.

[martinl88]

OK. I'm getting somewhere. Turns out neither STARTTLS or sending without encryption isn't supported and result in the error stated above. When I used regular SSL/TLS, then the invites started moving.

So, the new question is, how can I configure the encryption part of the SMTP connection?

[begemotik]

SMTP_TLS_CIPHERS=TLSv1.2
SMTP_SECURE=false

I think you actually never use TLS if you set SMTP_SECURE=false

Thanks @binaryfire for your finding, it really helped me to setup notification with SES.

[sourcecodemage]

@tommoor I think it might be worth adding "STARTTLS isn't supported" to the docs. I was trying to use Amazon SES over port 587 (STARTTLS) and was getting the same error mentioned here. As soon as I switched to port 465 (regular TLS) it worked.

Ref: https://docs.aws.amazon.com/ses/latest/dg/smtp-connect.html

Nice. Did you have any other settings? Like "SMTP_TLS_CIPHERS" or "SMTP_SECURE" ?

[binaryfire]

@majorgear Nope, just this:

SMTP_HOST=email-smtp.eu-central-1.amazonaws.com
SMTP_PORT=465
SMTP_USERNAME={{ aws_ses_username }}
SMTP_PASSWORD={{ aws_ses_password }}
SMTP_FROM_EMAIL=docs@mydomain.dev
SMTP_REPLY_EMAIL=noreply@mydomain.dev

[sourcecodemage]

Thx. My use case was for Apple / iCloud mail. I discovered that this was covered in their wiki.

It's a bit different than yours, but I appreciate your response.

SMTP_HOST=smtp.mail.me.com
SMTP_PORT=587
SMTP_USERNAME=<username>
SMTP_PASSWORD=<password>
SMTP_FROM_EMAIL=<email>
SMTP_TLS_CIPHERS=TLSv1.2
SMTP_SECURE=false

[Sleepful]

They still haven't added "STARTTLS isn't supported" to the docs 🤦
Took me a long handful of hours to find out the hard way...

[thetractor]

I try to get this working with Postmark. Non of the above solutions helped getting things working. Here my configuration:

SMTP_HOST=smtp.postmarkapp.com
SMTP_PORT=587
SMTP_USERNAME=<API-TOKEN>
SMTP_PASSWORD=<API-TOKEN>
SMTP_FROM_EMAIL=email@example.com
SMTP_REPLY_EMAIL=email@example.com

I tried with ports 25, 587 and 465 (which is not supported according to postmark's docs). Also triede many different settings for the SMTP_TLS_CIPHERS variable - no luck.

The error I am getting is this:

app-outline-1       | {"error":"38DB86990D7F0000: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 email@example.com","stack":"Error: 38DB86990D7F0000:error:0A00010B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:354:\n"}

Any suggestions?

[Sleepful]

Postmark doesn't offer TLS, only STARTTLS, so you are out of luck with Outline if your provider is Postmark, which is a shame. If you have your own Postfix server with a relay to Postmark, you could do that... but it might be easier to just add STARTTLS to Outline lol

[Sleepful]

And not using encryption is a really iffy thing to do 🤦

[tommoor]

STARTTLS has always been supported by Outline, we' just use nodemailer as the module for sending emails – it's a very straight forward implementation

[Sleepful]

@tommoor is that written somewhere in the docs? Would be good to add. I tried to use it and failed to do so 😄

[tommoor]

Happy to add something to the docs if you have a suggestion for what would help here.