Issue: Can't use custom SMTP with Outlook-Connected Personal Email-Outlook Extension

[ssweber]

I was trying to avoid disabling the 'Security Defaults' in Exchange and enabling Outlook SMTP. So instead I connected IMAP with the paid extension and put in a Mailgun account for the SMTP. It however doesn't work. I'm wondering if the extension assumes the same credentials as IMAP? (For now I will investigate allowing SMTP in exchange for my user)

Steps to reproduce:

1. Setup Outlook extension
2. Setup IMAP for Personal Account. Test to verify it's working
3. Setup alternate SMTP account in same 'Connected' Personal Email. It will not work.
4. Add same SMTP credentials to new personal email address (not Outlook connected). See that test email works there.

Thank you. Really enjoying using Espo.

Some images of my setup:





Console:

XHRPOST
https://crm.MYSITE.com/api/v1/Email/sendTest
[HTTP/2 500 619ms]


messageTranslation Object { label: "unknownError", scope: "Email", data: {} }
label "unknownError"
scope "Email"
data Object { }​

[victor]

Try smtp.office365.com in the Host field. Also specify the other parameters identically: Port, Security, Auth and Auth Mechanism.



If it does not help, then enable Debug mode: https://docs.espocrm.com/administrat...ng/#debug-mode and send an error log. EspoCRM log files are located in your_instance_name/data/logs/ directory. Most errors are logger there.

[ssweber]

Oof. I totally skipped the end of the setup instruction guide for Outlook - https://docs.espocrm.com/extensions/...on/setting-up/

"For Office 365 you might need to enable SMTP AUTH for specific mailboxes".

Instead of 'might' that should probably say 'For Office 365, verify that `Authenticated SMTP` is checked for each CRM user in the Microsoft 365 admin center.' And then list the steps.

[ssweber]

Per this issue, I was trying to use a different SMTP provider for the Outlook IMAP. However, after reviewing again I was able to FIX the Outlook SMTP sending (even with 'Security Defaults' enabled)

Per instructions in https://learn.microsoft.com/en-us/ex...mtp-submission

1. Use the Microsoft 365 admin center to enable or disable SMTP AUTH on specific mailboxes (mine is at
2. Open the Microsoft 365 admin center and go to Users > Active users.
3. Select the user, and in the flyout that appears, select Mail.
4. In the Email apps section, select Manage email apps.
5. Verify the Authenticated SMTP setting: unchecked = disabled, checked = enabled.
6. When you're finished, select Save changes.

It should look like:

[ssweber]

You can consider this issue 'Closed'. Now that I resolved using Outlook for the SMTP as well, there's really no reason to use an external provider.