Magic signin link not sent since 1.7.0 / 0.81.0 update

[nebulon]

Is there anything in the app logs about this? Also if you do not see the mail in the mail server eventlog itself, then this is likely an outline bug itself with that version. Have you looked in their issue tracker already?

[gerard]

@nebulon Yes, I found an error in the logs:

Mail command failed: 550 Authenticated user (removed@mydomain) cannot send mail as (removed) ... at SMTPConnection._formatError (/app/code/node_modules/nodemailer/lib/smtp-connection/index.js:798:19)\n at SMTPConnection._actionMAIL (/app/code/node_modules/nodemailer/lib/smtp-connection/index.js:1607:34)\n at SMTPConnection.<anonymous> (/app/code/node_modules/nodemailer/lib/smtp-connection/index.js:1076:18)\n at SMTPConnection._processResponse (/app/code/node_modules/nodemailer/lib/smtp-connection/index.js:982:20)\n at SMTPConnection._onData (/app/code/node_modules/nodemailer/lib/smtp-connection/index.js:763:14)\n at SMTPConnection._onSocketData (/app/code/node_modules/nodemailer/lib/smtp-connection/index.js:195:44)\n at Socket.emit (node:events:517:28)\n at Socket.emit (node:domain:489:12)\n at addChunk (node:internal/streams/readable:335:12)\n at readableAddChunk (node:internal/streams/readable:308:9)\n at Readable.push (node:internal/streams/readable:245:10)\n at TCP.onStreamRead (node:internal/stream_base_commons:190:23)"}

[joseph]

@gerard did you happen to configure the mail from address of outline? Cloudron will block apps from sending emails with unknown addresses. You have to configure outline like this - https://docs.cloudron.io/apps/#mail-from-address

[gerard]

@joseph No, I didn't change the email settings through Outline. I used the app's "Email" setting as described under your link.

I have also tried further troubleshooting: I setup an additional outline instance on the same server, using the same domain (different subdomain o course) and the same email settings.
Then I added a new member through the outline preferences.
The problem was instantly reproduced.

The main user received the "Welcome to outline" email
The new member received the "XX invited you to join Outline..." message.
But when trying to login, the email with the magic signing link is not being sent. Same error in the logs as described above.

For information: I'm using an external SMTP server for this domain. This email settings worked well before the update. They also still work well with other apps, for example WordPress.

[nebulon]

I can reproduce the last issue, I can't see any SMTP failures though.

For some reason after inviting the user, the link in the email is only a regular https://outline.domain.com/?ref=invite-email link which has no magic token or so, so after visiting that trying to login by typing the email will do nothing as for some reason no user was actually created looking at the members page.

Seems like a flow issue in the app itself.

Edit: the user is there but still "inactive" and only invited, but even resending the invite link does not actually produce a proper invite link with any kind of token

Edit2: manually resending the invite did trigger the SMTP issue here. Investigating....

[nebulon]

Alright so the issue is that the app generates a random reply-to address with which it sends out invite mails: https://github.com/outline/outline/blob/bb43c24efef817cdbc76d4e90781355897280c0b/server/emails/templates/BaseEmail.tsx#L191

Apps are not allowed to send out emails with random addresses on Cloudron. Not sure how to solve this right now.

[nebulon]

I have created an upstream discussion about this at https://github.com/outline/outline/discussions/7949

Also, we will release a locally patched app package to make it work. The current "patch" is https://git.cloudron.io/cloudron/outline-app/-/commit/26c17f516c1ec39e46e66df9acb8cfa8ff5a70f7

[gerard]

@nebulon Thank you for your quick action . Any ETA on the locally patched app?.

[nebulon]

The patched package is out now.

[gerard]

@nebulon Unfortunately it's still not working for me.

The From Name is "CrunchBox" - The From address is team@crunchbox.lu

The error log shows the following:

... cannot send mail as \"CrunchBox team\"@crunchbox.lu", ...

Update:
I thought that the From Name might be interpreted as part of the address, so I tried removing the From Name. But then it is automatically set to "Outline" .

[nebulon]

Is this because you set the email address for outline in the Cloudron dashboard? And other mails are still sent out?

[gerard]

@nebulon I set the e-mail addres for Outline in the Cloudron dashboard. (I used a clean test-instance of Outline, which I updated to package v1.7.1)
Then I logged in with the Cloudron SSO to create a new user.
The "invitation email" was sent and received:

Nov 14 16:17:38 - {"label":"worker","level":"info","message":"EmailTask running","props":{"actorEmail":"gerard@mailo.com","actorName":"Gérard Kieffer","name":"Gérard","teamName":"Outline","teamUrl":"https://workspace2.crunchbox.lu","to":"gnkieffer@gmail.com"},"templateName":"InviteEmail"}
Nov 14 16:17:38 - {"label":"email","level":"info","message":"Sending email \"Gérard Kieffer invited you to join Outline’s workspace\" to gnkieffer@gmail.com"}

Then I opend the login page, entered the new user's email address and clicked the Sign In button. That email, containing the magic sign, failed to be sent:

Nov 14 16:17:49 - {"label":"worker","level":"info","message":"EmailTask running","props":{"client":"web","teamUrl":"https://workspace2.crunchbox.lu","to":"gnkieffer@gmail.com","token":"[Filtered]"},"templateName":"SigninEmail"}
Nov 14 16:17:49 - {"label":"email","level":"info","message":"Sending email \"Magic signin link\" to gnkieffer@gmail.com"}
Nov 14 16:17:49 - {"error":"Mail command failed: 550 Authenticated user team@crunchbox.lu cannot send mail as \"CrunchBox team\"@crunchbox.lu","level":"error","message":"Error sending email to gnkieffer@gmail.com","stack":"Error: Mail command failed: 550 Authenticated user team@crunchbox.lu cannot send mail as \"CrunchBox team\"@crunchbox.lu\n at SMTPConnection._formatError (/app/code/node_modules/nodemailer/lib/smtp-connection/index.js:798:19)\n at SMTPConnection._actionMAIL (/app/code/node_modules/nodemailer/lib/smtp-connection/index.js:1607:34)\n at SMTPConnection.<anonymous> (/app/code/node_modules/nodemailer/lib/smtp-connection/index.js:1076:18)\n at SMTPConnection._processResponse (/app/code/node_modules/nodemailer/lib/smtp-connection/index.js:982:20)\n at SMTPConnection._onData (/app/code/node_modules/nodemailer/lib/smtp-connection/index.js:763:14)\n at SMTPConnection._onSocketData (/app/code/node_modules/nodemailer/lib/smtp-connection/index.js:195:44)\n at Socket.emit (node:events:517:28)\n at Socket.emit (node:domain:489:12)\n at addChunk (node:internal/streams/readable:335:12)\n at readableAddChunk (node:internal/streams/readable:308:9)\n at Readable.push (node:internal/streams/readable:245:10)\n at TCP.onStreamRead (node:internal/stream_base_commons:190:23)"}
Nov 14 16:17:49 - {"error":"Mail command failed: 550 Authenticated user team@crunchbox.lu cannot send mail as \"CrunchBox team\"@crunchbox.lu","level":"error","message":"Error processing task in EmailTask","stack":"Error: Mail command failed: 550 Authenticated user team@crunchbox.lu cannot send mail as \"CrunchBox team\"@crunchbox.lu\n at SMTPConnection._formatError (/app/code/node_modules/nodemailer/lib/smtp-connection/index.js:798:19)\n at SMTPConnection._actionMAIL (/app/code/node_modules/nodemailer/lib/smtp-connection/index.js:1607:34)\n at SMTPConnection.<anonymous> (/app/code/node_modules/nodemailer/lib/smtp-connection/index.js:1076:18)\n at SMTPConnection._processResponse (/app/code/node_modules/nodemailer/lib/smtp-connection/index.js:982:20)\n at SMTPConnection._onData (/app/code/node_modules/nodemailer/lib/smtp-connection/index.js:763:14)\n at SMTPConnection._onSocketData (/app/code/node_modules/nodemailer/lib/smtp-connection/index.js:195:44)\n at Socket.emit (node:events:517:28)\n at Socket.emit (node:domain:489:12)\n at addChunk (node:internal/streams/readable:335:12)\n at readableAddChunk (node:internal/streams/readable:308:9)\n at Readable.push (node:internal/streams/readable:245:10)\n at TCP.onStreamRead (node:internal/stream_base_commons:190:23)"}

[nebulon]

Ah ok, so upstream mentioned to revert that change, so then we can debug the custom email from Cloudron once we know how the new upstream code behaves.

[gerard]

There seems to be the fix for the next release:
https://github.com/outline/outline/commit/6421995b29f40d4172cd342fd592b78d5707258c