Configuring TLS email

[j-kia]

Email connection fails when I'm using email service

To Reproduce

I want to use TLS so set SMTP Secure to true (I also tried port 465)

EMAIL_TRANSPORT: 'smtp'
EMAIL_FROM: 'kurs@axelina.com'
EMAIL_SMTP_HOST: 'smtp-relay.gmail.com'
EMAIL_SMTP_PORT: 25
EMAIL_SMTP_USER: ***********
EMAIL_SMTP_PASSWORD: *********
EMAIL_SMTP_SECURE: 'true'

Errors Shown

Error when EMAIL_SMTP_SECURE is true

[Error: 139748882389808:error:1408F10B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:332:
] {
  library: 'SSL routines',
  function: 'ssl3_get_record',
  reason: 'wrong version number',
  code: 'ESOCKET',
  command: 'CONN'
}
10:00:51 🚨 139748882389808:error:1408F10B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:332:
 
Error: 139748882389808:error:1408F10B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:332:

10:00:51 ✨ request errored POST 500 /email/admin 166ms
10:00:51 ⚠️  Email connection failed:
10:00:51 ⚠️  139748882389808:error:1408F10B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:332:

[jamescammarano]

I followed instructions also using a google email. Here is my config:

EMAIL_FROM="<MY_OTHER_EMAIL>@gmail.com"
EMAIL_TRANSPORT="smtp"

# ## Email (SMTP Transport)
# EMAIL_SMTP_POOL=true
EMAIL_SMTP_HOST="smtp.gmail.com"
EMAIL_SMTP_PORT=465
# EMAIL_SMTP_IGNORE_TLS=false
EMAIL_SMTP_USER="<MY_EMAIL>@gmail.com"
EMAIL_SMTP_PASSWORD="<APP_SPECIFIC_PASSWORD>"
EMAIL_SMTP_SECURE=true # Use TLS

I tested the mailing ability through an @mention in a comment on an item.

It was able to send and I was able to receive it. I did have to set an app-specific password through google but that didn't give me the same error.
https://support.google.com/mail/?p=InvalidSecondFactor

With port 25 I got:

[INTERNAL_SERVER_ERROR] connect ETIMEDOUT 209.85.232.109:25

Which was also not your error.

Is there a specific place you were using the email system?

[j-kia]

Is there a specific place you were using the email system?

I get this error all the time wherever i want to use the email service. When sending invitation mail with directus app or using MailsService in custom endpoints to send email with template

[rijkvanzanten]

@j-kia Try setting EMAIL_SMTP_SECURE to false. When false, nodemailer will automatically decide whether or not to use SSL based on the host used

[j-kia]

Try setting EMAIL_SMTP_SECURE to false. When false, nodemailer will automatically decide whether or not to use SSL based on the host used

I set it to false and get Connection timeout error

[j-kia]

I updated openssl and now it doesn't give me the wrong version number error, Now i just have Connection timeout error no matter setting EMAIL_SMTP_SECURE to true or false .

[jamescammarano]

Did you change your port back to 465? I got that error on port 25.

[j-kia]

@jaycammarano yes you're right, I was using port 25, I change it to 465 and now i get:

Invalid login: 535-5.7.8 Username and Password not accepted.

I checked username and password and it was correct. it seems i should allow less secure app in my account settings.
I will let you know if the problem is solved by doing this.

[jamescammarano]

@jaycammarano yes you're right, I was using port 25, I change it to 465 and now i get:

Invalid login: 535-5.7.8 Username and Password not accepted.

I checked username and password and it was correct. it seems i should allow less secure app in my account settings. I will let you know if the problem is solved by doing this.

Did you set an app-specific password with Google? I had to do that.

[rijkvanzanten]

It sounds to me like this is most likely a configuration issue, lets keep this discussion going in Discussions 👍🏻

[dataexcess]

Hi! I would love to accomplish this too! Where can I make the app specific password?
I cannot seem to make it work on my google account

[dataexcess]

Ok for me it started working once I enabled 'less secure app access' in google 🙌

[mattjcowan]

Getting similar error with a very simple SMTP endpoint:

Config settings (blah.com is fake domain, but same otherwise):

EMAIL_FROM="myuser@blah.com"
EMAIL_TRANSPORT="smtp"
EMAIL_SMTP_HOST="mail.blah.com"
EMAIL_SMTP_PORT=25
EMAIL_SMTP_SECURE=false

I verified that it works using swaks (a simple smtp test tool), it's able to send email with that host over port 25:

swaks --to myemail@mydomain.com --server mail.blah.com --port 25

Any ideas?

[mattjcowan]

Hmm, got it to work with double quotes around the port ... EMAIL_SMTP_PORT="25"

[azrikahar]

That would be odd indeed 🤔 would you be able to try verify whether removing the quotes again will make it not working anymore?

Personally had success with the following docker compose for testing purposes (without quotes around EMAIL_SMTP_PORT):

services:
    directus:
        image: directus/directus:9.18.1
        ports:
            - 8055:8055
        environment:
            - KEY=directus-key
            - SECRET=directus-secret
            - ADMIN_EMAIL=admin@example.com
            - ADMIN_PASSWORD=password
            - EMAIL_TRANSPORT=smtp
            - EMAIL_SMTP_HOST=maildev
            - EMAIL_SMTP_PORT=1025

    maildev:
        image: maildev/maildev:latest
        ports:
            - 1080:1080 # Maildev Web UI

so not sure what could be the possible cause. With that said, I'd also recommend using a Nodemailer script if possible if you ever run into any other errors again, similar to what was done here: #15183 (comment). That way it should be easier to pinpoint whether it's something to do with Nodemailer (what is being used when configuring SMTP email transport in Directus) or Directus side of things.

[mattjcowan]

Ok, so now I go back in and I can't reproduce and tried a couple setups on different machines (windows/linux, node 14 and 16), so not sure what happened. Thanks for the prompt to double check @azrikahar !! I'm still curious to what triggered that error then, I'll stay on the lookout.