smtp mail failed

Resolved kerm007
(@kerm007)

3 years, 4 months ago

hello im trying to make the smtp plugin work internally on a web site im testing if i setup the account without authentication it work

if in revenge i try to use authentication i enter my credential on the setting it failed all the time with error :

Could not authenticate your SMTP account.

This means we were able to connect to your SMTP host, but were not able to proceed using the email/password in the settings.

Typically this error is returned when the email or password is not correct or is not what the SMTP host is expecting.

im sure about the user name and password

what else i could check ?

Regards

Viewing 15 replies - 1 through 15 (of 42 total)

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Plugin Support Dake
(@dakeg)

3 years, 4 months ago

Hi @kerm007

Thanks for reaching out to us and we’re sorry to hear that you’re having issues setting up the Other SMTP mailer.

Just for reference, what SMTP service are you trying to connect to using the Other SMTP mailer?

Also, in case it helps, please ensure that you had followed the instructions outlined in this section of our documentation regarding generating an app password.

I hope this helps 🙂

Thread Starter kerm007
(@kerm007)

3 years, 4 months ago

hello

im using Other SMTP i pretty sure i setup everything fine

smtp host, tls ,smtp port ,authentication on my username and password

but it failed

Thanks

im trying to setup my exchange on prem server

Plugin Support Dake
(@dakeg)

3 years, 4 months ago

Hi @kerm007

Thanks for getting back to us.

I’m aware that you’re using the Other SMTP mailer, but I wanted to confirm what SMTP host you were connecting to. Based on the last line in your reply, it sounds like you are using Microsoft Exchange.

In that case, are you using your Microsoft account credentials directly or are you using an app password that was generated?

Thread Starter kerm007
(@kerm007)

3 years, 4 months ago

im entering my login and password in the field in the WP Mail Smtp

Thanks

Plugin Support Dake
(@dakeg)

3 years, 4 months ago

Hi @kerm007

Thank you for getting back to me.

Please try generating an app password for your Microsoft account by following the instructions outlined here instead of using your actual account credentials.

If the error still appears, after sending a test email, please provide the full error log that would appear afterward.
Thread Starter kerm007
(@kerm007)

3 years, 4 months ago
hello

i dont use MFA plus im not on O365 can i generate a password even in the OWA ?

Thanks
- This reply was modified 3 years, 4 months ago by kerm007.
Thread Starter kerm007
(@kerm007)

3 years, 4 months ago
hello

since i have no way to generate a password app here the full log

Thanks
```
Versions:
WordPress: 6.1.1
WordPress MS: No
PHP: 8.2.0
WP Mail SMTP: 3.7.0

Params:
Mailer: smtp
Constants: No
ErrorInfo: SMTP Error: Could not authenticate.
Host: mail.server.com
Port: 25
SMTPSecure: string(0) ""
SMTPAutoTLS: bool(false)
SMTPAuth: bool(true)

Server:
OpenSSL: OpenSSL 3.0.7 1 Nov 2022
Apache.mod_security: No

Debug:
Mailer: Other SMTP
SMTP Error: Could not authenticate.

SMTP Debug:
2023-01-31 13:58:13 Connection: opening to mail.server.com:25, timeout=300, options=array()

2023-01-31 13:58:13 Connection: opened

2023-01-31 13:58:13 SERVER -> CLIENT: 220 server.ibexpharma.com Microsoft ESMTP MAIL Service ready at Tue, 31 Jan 2023 08:58:13 -0500

2023-01-31 13:58:13 CLIENT -> SERVER: EHLO localhost

2023-01-31 13:58:13 SERVER -> CLIENT: 250-server.ibexpharma.com Hello [192.168.2.58]250-SIZE 37748736250-PIPELINING250-DSN250-ENHANCEDSTATUSCODES250-STARTTLS250-X-ANONYMOUSTLS250-AUTH NTLM250-X-EXPS GSSAPI NTLM250-8BITMIME250-BINARYMIME250-CHUNKING250 XRDST

SMTP Error: Could not authenticate.

2023-01-31 13:58:13 CLIENT -> SERVER: QUIT

2023-01-31 13:58:13 SERVER -> CLIENT: 221 2.0.0 Service closing transmission channel

2023-01-31 13:58:13 Connection: closed

SMTP Error: Could not authenticate.
```
Plugin Support Dake
(@dakeg)

3 years, 4 months ago

Hi @kerm007

So long as you have access to a Microsoft account, you should be able to generate an app password.

To add some context, basic authentication with SMTP (original login credentials) was deprecated back in October of last year by Microsoft. Microsoft requires that you enable MFA to generate an app password.

The app you are using shouldn’t be an issue because I imagine you needed a Microsoft account of some kind to utilize their service.

Here are some straightforward instructions for generating an app password directly from the security settings page of your Microsoft account.

Thread Starter kerm007
(@kerm007)

3 years, 4 months ago

i dont have a microsoft account

im using exchange on prem i check in my OWA and there is nothing to generated a app password

what else i can do ?

Thanks

Plugin Support Dake
(@dakeg)

3 years, 4 months ago

Hi @kerm007

Thank you for clarifying and I apologize for the misunderstanding. I assumed you were using a Microsoft account since you were using multiple Microsoft-specific services.

So that we can glean more insight into what might be going on, please enable “Debug email sending” in your WP Mail Settings, send another test email, then provide us with the new error log. Enabling this option provides us with more specific information.

Again, I apologize for the back-and-forth while we investigate this issue.
Thread Starter kerm007
(@kerm007)

3 years, 4 months ago
Hello

here the new log after enabling the the option:
```
Versions:
WordPress: 6.1.1
WordPress MS: No
PHP: 8.2.0
WP Mail SMTP: 3.7.0

Params:
Mailer: smtp
Constants: No
ErrorInfo: SMTP Error: Could not authenticate.
Host: server.ibexpharma.com
Port: 25
SMTPSecure: string(0) ""
SMTPAutoTLS: bool(false)
SMTPAuth: bool(true)

Server:
OpenSSL: OpenSSL 3.0.7 1 Nov 2022
Apache.mod_security: No

Debug:
Mailer: Other SMTP
SMTP Error: Could not authenticate.

SMTP Debug:
2023-01-31 16:03:40 Connection: opening to server.ibexpharma.com:25, timeout=300, options=array()

2023-01-31 16:03:40 Connection: opened

2023-01-31 16:03:40 SERVER -> CLIENT: 220 server.ibexpharma.com Microsoft ESMTP MAIL Service ready at Tue, 31 Jan 2023 11:03:39 -0500

2023-01-31 16:03:40 CLIENT -> SERVER: EHLO localhost

2023-01-31 16:03:40 SERVER -> CLIENT: 250-serverS.ibexpharma.com Hello [192.168.2.58]250-SIZE 37748736250-PIPELINING250-DSN250-ENHANCEDSTATUSCODES250-STARTTLS250-X-ANONYMOUSTLS250-AUTH NTLM250-X-EXPS GSSAPI NTLM250-8BITMIME250-BINARYMIME250-CHUNKING250 XRDST

SMTP Error: Could not authenticate.

2023-01-31 16:03:40 CLIENT -> SERVER: QUIT

2023-01-31 16:03:40 SERVER -> CLIENT: 221 2.0.0 Service closing transmission channel

2023-01-31 16:03:40 Connection: closed

SMTP Error: Could not authenticate.
```
Plugin Support Dake
(@dakeg)

3 years, 4 months ago

Hi @kerm007

Thank you. Can you also provide us with the latest debug event? Please ensure to either screenshot or copy and paste the full event information

Thread Starter kerm007
(@kerm007)

3 years, 4 months ago

hello

i went and there is nothing in the Debug Events

Thanks

Plugin Support Dake
(@dakeg)

3 years, 4 months ago

Hi @kerm007

That certainly is strange. We would recommend checking Tools>Site Health to verify that all of our plugin tables are created and check your WordPress debug.log in case there are any errors that prevent Debug Event creation.

We would also recommend deactivating all plugins and switching to a default WordPress twenty-* theme as well. You can also try setting up another mailer (for testing purposes) to verify that WP Mail SMTP is working correctly.
Thread Starter kerm007
(@kerm007)

3 years, 4 months ago
ok i will try different thing

this site is coming from a backup we want to use it in the future move it here internally im testing different thing but the mail feature is not working

i want to make it work

Thanks
- This reply was modified 3 years, 4 months ago by kerm007.
- This reply was modified 3 years, 4 months ago by kerm007.

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