iCloud email

Sampo2910

Hi,

So I am back using nodebb and setup went well.

But once again its an email problem like before. I want to use the iCloud in the 'select a service'

I have an icloud email alias address and app specific password that I have used and setup in email settings for nodebb.

I click send a test email and i get the message bottom right that email was successfully sent. No email arrives.

The above did not work until I added sendgrid plugin?? I dont use sendgrid so what can I do in this case?

What plugin will work for me. ?

And why do I have an option to use iCloud as a service if it does not work. I had all these problems many versions ago and seems nothing is resolved.

Any help much appreciated.

Thank you.

PitaJ

Previous discussions in:

https://github.com/NodeBB/NodeBB/issues/9796

https://community.nodebb.org/post/84785

You kind of just abandoned those, did you get it working back then or have you been without email the whole time?

Sampo2910

Hi,

The previous discussions did not really solve anything and still begs the question why is the option for iCloud there after all this time if it does not work?

Has anybody else managed to set it up. If so I would like to know the steps so I could compare.

Unfortunately I have not been well and hence a long period away. I am back again to try again, and really would like to setup with iCloud if possible. Do I need sendgrid installed and running? If it is not then i get a message saying sendmail executable is not installed..I assumed sendgrid was something apart from this and that nodeebb had its on 'built in' ??
Thx.

PitaJ

Let me explain some things.

There are three ways to send emails from NodeBB:

Emailer plugin. (Like sendgrid). These plugins allow you to use email distribution services like Sendgrid, MailChimp, etc to send out emails. This helps about issues of spam filtering and such, because it's their email servers handling all of that. These plugins contact the email service via http and then the service sends your emails out.
SMTP transport. This is built into NodeBB. It is only used if you don't have an emailer plugin active and you enable "Enable SMTP transport" (previously "Use an external server to send emails") in the email settings. The SMTP transport allows you to either pick from a list of known services (provided by the underlying module nodemailer) or to provide custom settings yourself. It contacts the server via SMTP and then the SMTP server sends your your emails.
Sendmail transport. This is also built in. It is only used if you don't have an emailer plugin active and you have the SMTP transport disabled ("Use an external server to send emails" or "Enable SMTP transport" OFF). It attempts to execute the "sendmail" executable of your system, which directly sends out the emails. This is rarely used because emails sent this way are practically guaranteed to be caught in a spam filter.

why is the option for iCloud there after all this time if it does not work

That list of services is not produced by us, and we haven't proven that the iCloud option actually doesn't work. We do know for sure that the SMTP transport works with Gmail, for instance.

Unfortunately I have not been well and hence a long period away.

Sorry to hear that.

Do I need sendgrid installed and running?

No. At I understand it, you are not trying to use Sendgrid to send out your emails.

If it is not then i get a message saying sendmail executable is not installed

If you get that error, then you haven't enabled the SMTP transport. Toggle it on in the email settings.

Sampo2910

Thanks very much for the detailed explanation. That clears a lot up for me.

So SMTP Transport is toggled to on for all these tests.

Using iCloud with encrypted smtp settings as explained here https://support.apple.com/en-us/HT202304 gives this message.
2022-01-25 22_58_03-Settings _ Email _ NodeBB Admin Control Panel.png

In Full: Error: 139675981281152:error:1408F10B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:332:

SMTP Settings with No encryption
2022-01-25 23_03_29-Settings _ Email _ NodeBB Admin Control Panel.png

With Start TLS (This error message is the same if you do not use 'Custom' and select 'iCloud' from the drop down.
2022-01-25 22_56_44-Settings _ Email _ NodeBB Admin Control Panel.png

Sampo2910

LOGS
2022-01-25T20:56:19.894Z [4567/81326] - [31merror[39m: admin.email.test
Error: Mail command failed: 530 5.7.0 Must issue a STARTTLS command first
at SMTPConnection._formatError (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:784:19)
at SMTPConnection._actionMAIL (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:1566:34)
at SMTPConnection.<anonymous> (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:1041:18)
at SMTPConnection._processResponse (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:947:20)
at SMTPConnection._onData (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:749:14)
at Socket.SMTPConnection._onSocketData (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:189:44)
at Socket.emit (events.js:375:28)
at addChunk (internal/streams/readable.js:290:12)
at readableAddChunk (internal/streams/readable.js:265:9)
at Socket.Readable.push (internal/streams/readable.js:204:10)
2022-01-25T20:56:40.035Z [4567/81326] - [31merror[39m: admin.email.test
Error: Invalid login: 535 5.7.8 Error: authentication failed
at SMTPConnection._formatError (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:784:19)
at SMTPConnection._actionAUTHComplete (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:1536:34)
at SMTPConnection.<anonymous> (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:540:26)
at SMTPConnection._processResponse (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:947:20)
at SMTPConnection._onData (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:749:14)
at TLSSocket.SMTPConnection._onSocketData (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:189:44)
at TLSSocket.emit (events.js:375:28)
at addChunk (internal/streams/readable.js:290:12)
at readableAddChunk (internal/streams/readable.js:265:9)
at TLSSocket.Readable.push (internal/streams/readable.js:204:10)
2022-01-25T20:57:12.849Z [4567/81326] - [31merror[39m: admin.email.test
Error: Invalid login: 535 5.7.8 Error: authentication failed
at SMTPConnection._formatError (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:784:19)
at SMTPConnection._actionAUTHComplete (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:1536:34)
at SMTPConnection.<anonymous> (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:540:26)
at SMTPConnection._processResponse (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:947:20)
at SMTPConnection._onData (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:749:14)
at TLSSocket.SMTPConnection._onSocketData (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:189:44)
at TLSSocket.emit (events.js:375:28)
at addChunk (internal/streams/readable.js:290:12)
at readableAddChunk (internal/streams/readable.js:265:9)
at TLSSocket.Readable.push (internal/streams/readable.js:204:10)
2022-01-25T20:57:13.170Z [4567/81326] - [31merror[39m: admin.email.test
Error: Invalid login: 535 5.7.8 Error: authentication failed
at SMTPConnection._formatError (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:784:19)
at SMTPConnection._actionAUTHComplete (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:1536:34)
at SMTPConnection.<anonymous> (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:540:26)
at SMTPConnection._processResponse (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:947:20)
at SMTPConnection._onData (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:749:14)
at TLSSocket.SMTPConnection._onSocketData (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:189:44)
at TLSSocket.emit (events.js:375:28)
at addChunk (internal/streams/readable.js:290:12)
at readableAddChunk (internal/streams/readable.js:265:9)
at TLSSocket.Readable.push (internal/streams/readable.js:204:10)
2022-01-25T20:58:02.741Z [4567/81326] - [31merror[39m: admin.email.test
Error: 139675981281152:error:1408F10B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:332:

2022-01-25T21:01:57.924Z [4567/81326] - [31merror[39m: admin.email.test
Error: Invalid login: 535 5.7.8 Error: authentication failed
at SMTPConnection._formatError (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:784:19)
at SMTPConnection._actionAUTHComplete (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:1536:34)
at SMTPConnection.<anonymous> (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:540:26)
at SMTPConnection._processResponse (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:947:20)
at SMTPConnection._onData (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:749:14)
at TLSSocket.SMTPConnection._onSocketData (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:189:44)
at TLSSocket.emit (events.js:375:28)
at addChunk (internal/streams/readable.js:290:12)
at readableAddChunk (internal/streams/readable.js:265:9)
at TLSSocket.Readable.push (internal/streams/readable.js:204:10)
2022-01-25T21:02:18.398Z [4567/81326] - [31merror[39m: admin.email.test
Error: Mail command failed: 530 5.7.0 Must issue a STARTTLS command first
at SMTPConnection._formatError (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:784:19)
at SMTPConnection._actionMAIL (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:1566:34)
at SMTPConnection.<anonymous> (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:1041:18)
at SMTPConnection._processResponse (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:947:20)
at SMTPConnection._onData (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:749:14)
at Socket.SMTPConnection._onSocketData (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:189:44)
at Socket.emit (events.js:375:28)
at addChunk (internal/streams/readable.js:290:12)
at readableAddChunk (internal/streams/readable.js:265:9)
at Socket.Readable.push (internal/streams/readable.js:204:10)
2022-01-25T21:03:27.139Z [4567/81326] - [31merror[39m: admin.email.test
Error: Mail command failed: 530 5.7.0 Must issue a STARTTLS command first
at SMTPConnection._formatError (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:784:19)
at SMTPConnection._actionMAIL (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:1566:34)
at SMTPConnection.<anonymous> (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:1041:18)
at SMTPConnection._processResponse (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:947:20)
at SMTPConnection._onData (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:749:14)
at Socket.SMTPConnection._onSocketData (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:189:44)
at Socket.emit (events.js:375:28)
at addChunk (internal/streams/readable.js:290:12)
at readableAddChunk (internal/streams/readable.js:265:9)
at Socket.Readable.push (internal/streams/readable.js:204:10)
2022-01-25T21:04:13.622Z [4567/81326] - [31merror[39m: admin.email.test
Error: Invalid login: 535 5.7.8 Error: authentication failed
at SMTPConnection._formatError (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:784:19)
at SMTPConnection._actionAUTHComplete (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:1536:34)
at SMTPConnection.<anonymous> (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:540:26)
at SMTPConnection._processResponse (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:947:20)
at SMTPConnection._onData (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:749:14)
at TLSSocket.SMTPConnection._onSocketData (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:189:44)
at TLSSocket.emit (events.js:375:28)
at addChunk (internal/streams/readable.js:290:12)
at readableAddChunk (internal/streams/readable.js:265:9)
at TLSSocket.Readable.push (internal/streams/readable.js:204:10)
2022-01-25T21:05:41.260Z [4567/81326] - [31merror[39m: admin.email.test
Error: Invalid login: 535 5.7.8 Error: authentication failed
at SMTPConnection._formatError (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:784:19)
at SMTPConnection._actionAUTHComplete (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:1536:34)
at SMTPConnection.<anonymous> (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:540:26)
at SMTPConnection._processResponse (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:947:20)
at SMTPConnection._onData (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:749:14)
at TLSSocket.SMTPConnection._onSocketData (/home/smiley/nodebb/node_modules/nodemailer/lib/smtp-connection/index.js:189:44)
at TLSSocket.emit (events.js:375:28)
at addChunk (internal/streams/readable.js:290:12)
at readableAddChunk (internal/streams/readable.js:265:9)
at TLSSocket.Readable.push (internal/streams/readable.js:204:10)
LOGS CONTROL PANEL

PitaJ

@sampo2910 just want to confirm what each image corresponds to.

First image: Encrypted security setting
Second image: NONE security setting
Third image: STARTTLS security setting (same as iCloud preset)

Have you tried using the same iCloud credentials from an email client like Thunderbird?

Sampo2910

@pitaj Thanks for the reply.

Yes the images were correct as you have said, although that will not matter when I have finished explaining.

So. Using the drop down method for iCloud will work.

I use an iCloud address for my own personal email and as I did not want to use that in my forum I had created an alias iCloud email. I also created an app specific password for NodeBB on my Apple ID page.

When setting up in NodeBB my thoughts were (stupid now) were that I need to setup and sign in using the alias email I had created along with the new app specific password. Not the case.

For anyone else that might try (or as dumb as me) then you can put your alias email address at the top here so it shows it came from that address. If anyone replies then of course it will go to my alias inbox. Fine with me.
2022-01-26 16_45_56-Window.png

Enable SMTP Transport, select iCloud as your service and use your MAIN iCloud email address (not the alias as I did) as your username and the app specific password you just created. All will work. Trust me.

In my defense to start with it was saying email successfully sent although nothing came. Then trying smtp settings you see what i got above. In the end it was all very simple and although I am sure some would have known that maybe some would not. We all have had the slap on the forehead moments and this was one for me. Hopefully it MAY help someone out in the future.

Big thanks to @PitaJ
Appreciate the time.

B-738

Me work well !