SMTP email

[j-kia]

Preflight Checklist

• I have completed all Troubleshooting Steps.
• I'm on the latest version of Directus.
• There's no other issue that already describes my problem.

Describe the Bug

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:

What version of Directus are you using?

9.4.3

What version of Node.js are you using?

16.13.1

What database are you using?

MySql

What browser are you using?

Any browser

What operating system are you using?

linux

How are you deploying Directus?

Docker

[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 👍🏻