SMTP integration works with default tenant, but not duplicated one

mculley

I successfully integrated SendGrid into my default tenant. I then duplicated the tenant and tested email and it fails. I created a new API key with SendGrid and it still fails.

Unable to send email via JavaMail
Prime Messaging Exception

I am confused by the last part of the event log msg:

message successfully delivered to mail server

Here is the event log msg.

Email debug information

7/21/2023 10:32:29 PM Z DEBUG: getProvider() returning jakarta.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Oracle]
DEBUG SMTP: need username and password for authentication
DEBUG SMTP: protocolConnect returning false, host=smtp.sendgrid.net, user=apikey, password=<null>
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "smtp.sendgrid.net", port 587, isSSL false
220 SG ESMTP service ready at geopod-ismtpd-1
DEBUG SMTP: connected to host "smtp.sendgrid.net", port: 587
EHLO hiddenlayer-1.instance.fusionauth.io
250-smtp.sendgrid.net
250-8BITMIME
250-PIPELINING
250-SIZE 31457280
250-STARTTLS
250-AUTH PLAIN LOGIN
250 AUTH=PLAIN LOGIN
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "PIPELINING", arg ""
DEBUG SMTP: Found extension "SIZE", arg "31457280"
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Found extension "AUTH", arg "PLAIN LOGIN"
DEBUG SMTP: Found extension "AUTH=PLAIN", arg "LOGIN"
STARTTLS
220 Begin TLS negotiation now
EHLO hiddenlayer-1.instance.fusionauth.io
250-smtp.sendgrid.net
250-8BITMIME
250-PIPELINING
250-SIZE 31457280
250-STARTTLS
250-AUTH PLAIN LOGIN
250 AUTH=PLAIN LOGIN
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "PIPELINING", arg ""
DEBUG SMTP: Found extension "SIZE", arg "31457280"
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Found extension "AUTH", arg "PLAIN LOGIN"
DEBUG SMTP: Found extension "AUTH=PLAIN", arg "LOGIN"
DEBUG SMTP: protocolConnect login, host=smtp.sendgrid.net, user=apikey, password=<non-null>
DEBUG SMTP: Attempt to authenticate using mechanisms: LOGIN PLAIN DIGEST-MD5 NTLM XOAUTH2 
DEBUG SMTP: Using mechanism LOGIN
DEBUG SMTP: AUTH LOGIN command trace suppressed
DEBUG SMTP: AUTH LOGIN succeeded
DEBUG SMTP: use8bit false
MAIL FROM:<support@hiddenlayer.com>
250 Sender address accepted
RCPT TO:<mculley@hiddenlayer.com>
250 Recipient address accepted
DEBUG SMTP: Verified Addresses
DEBUG SMTP:   mculley@hiddenlayer.com
DATA
354 Continue
Date: Fri, 21 Jul 2023 22:32:28 +0000 (UTC)
From: support@hiddenlayer.com
Reply-To: support@hiddenlayer.com
To: mculley@hiddenlayer.com
Message-ID: <1132593178.71.1689978748428@hiddenlayer-1.instance.fusionauth.io>
Subject: FusionAuth SMTP Test
MIME-Version: 1.0
Content-Type: multipart/alternative; 
	boundary="----=_Part_70_1022356550.1689978748428"

------=_Part_70_1022356550.1689978748428
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 7bit

Congratulations! You have successfully configured the SMTP server.

Tenant Id: 6528d22f-2bc0-dd01-7cd5-bf80935474a3
Tenant name: stage

Host: smtp.sendgrid.net
Port: 587
Username: apikey
Security: TLS


- FusionAuth
------=_Part_70_1022356550.1689978748428
Content-Type: text/html; charset=UTF-8
Content-Transfer-Encoding: 7bit

<p>
Congratulations! You have successfully configured the SMTP server.
</p>

<table style="margin-bottom: 10px;">
  <tr>
    <td><strong>Tenant Id:</strong></td>
    <td>6528d22f-2bc0-dd01-7cd5-bf80935474a3</td>
  </tr>
  <tr>
    <td><strong>Tenant name:</strong></td>
    <td>stage</td>
  </tr>
</table>

<table style="margin-bottom: 10px;">
  <tr>
    <td><strong>Host:</strong></td>
    <td>smtp.sendgrid.net</td>
  </tr>
  <tr>
    <td><strong>Port:</strong></td>
    <td>587</td>
  </tr>
  <tr>
    <td><strong>Username:</strong></td>
    <td>apikey</td>
  </tr>
  <tr>
    <td><strong>Security:</strong></td>
    <td>TLS</td>
  </tr>
</table>


<p>
- FusionAuth
</p>

------=_Part_70_1022356550.1689978748428--
.
250 Ok: queued as EoKj0DJlSLOG1mgulDMzmg
DEBUG SMTP: message successfully delivered to mail server
QUIT
221 See you later

mculley

@mark-robustelli

I tried reconfiguring this again and was successful. I do not know if It was user error the first three times and not the fourth or if I changed the configuration somehow that resulted in the desired behavior.

mark.robustelli

Did you check the SMTP settings in the duplicated tenant? The password does not copy when it is duplicated.

https://fusionauth.io/docs/v1/tech/core-concepts/tenants#overview

"When using the duplicate feature for Tenants, the SMTP password is not copied. You will have to enter this manually before sending emails.

mculley

@mark-robustelli

yes. The SendGrid API key is the password

mark.robustelli

@mculley When you go edit the copied tenants settings and send a test email. Does that work for you?

Screenshot 2023-07-28 at 8.59.06 AM.png

The response should look something like this:
Screenshot 2023-07-28 at 9.00.31 AM.png

If that works, I would check the SendGrid activity for failure (it may take a while to show up in the activity) Screenshot 2023-07-28 at 9.03.26 AM.png :

I'm thinking Sendgrid may be blocking it for some reason if FusionAuth thinks the send worked.

mculley

@mark-robustelli

No, it does not. That is my original description of the problem.

I created a stage tenant and configured SMTP for SendGrid.
Email test was successful.
I created a tenant named prod.
The SMTP configuration was auto-added to the prod tenant
prod send test email failed.
I then went through each prod SMTP field one by one and made sure it was correct. I even generated a new API key.
prod send test email again failed.

mculley

@mark-robustelli

I am having other trouble that makes me wonder if there is some configuration in the tenant that I am not understanding or is not correct. Specifically, I am using Postman to send in a request to the /api/entity/search endpoint. Works for the stage tenant but I cannot get the same request to work when I change X-FusionAuth-TenantId to the id of prod tenant.

To summarize, for the prod tenant, neither of these two things work:

Send Test Email
/api/entity/search

mculley

@mark-robustelli

PS: The /api/entity/search request fails with Http Code 401

mark.robustelli

@mculley Thanks for the info. I took a look and it appears you have access to the Account Portal. If this is a time sensitive issue you can receive more timely support by opening a ticket since you have a support contract with FusionAuth.

In the mean-time, was not able to re-create your SMTP issue and appeared to work on my end. I will also spin your question about the entity serach onto another topic and take a look at if over the next couple of days. You can find the question here: Problem with entity search after copying Tenant.

mculley

@mark-robustelli

I tried reconfiguring this again and was successful. I do not know if It was user error the first three times and not the fourth or if I changed the configuration somehow that resulted in the desired behavior.

mark.robustelli

@mculley , in any case, I am glad it is working for you. I think the important take away here is that if this happens again or something else comes up and you need timely support, you have access to the Account Portal.

Of course we are always glad to see you here in the forum as well.

mculley

@mark-robustelli

right on. I will use that next time.