I am migrating from Exchange to O365  and am testing mailit using the supplied EmailClient Filemaker database provided. I get the following error. 

530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [BN6PR1001CA0036.namprd10.prod.outlook.com]

Is this 365 related or plugin related?

Edited July 26, 20197 yr by accfanz

This is an error back from the server.

Microsoft gives this explanation of the error:

Quote

This indicates that you are connecting to the SMTP client submission endpoint (smtp.office365.com), which can't be used for direct send. For direct send, use the MX endpoint for your Office 365 tenant, which ends with "mail.protection.outlook.com." You can find your MX endpoint by following the steps here.

It typically means that you authenticated with one account in the EmailConnectSMTP function but set the From address to another account in EmailCreate which is not allowed. You may be able to configure Office365 to allow this but I cannot tell you how to do so. 

I am also running into this issue and believe I have it set up correctly. 

EmailConnectSMTP Username: globals_USERS::Email

EmailCreate From: globals_USERS::Name_Full & "<" & globals_USERS::Email & ">"

Could it be because I'm adding the full name? I thought that was a suggested way to do it to avoid being put in a spam filter.

Additionally (only because it's tangentially related) I do have EmailConnectIMAP disabled. Don't think that's relevant but felt like I should mention it. 

 

Update: FWIW I just checked my plugin version and I'm on 3.1 while the machines that are unable to send are on 3.3.

Update 2: If I log in as one of the affected users I get the same error on my machine as well. So it's not plugin version, it's account related. 

Update 3: I'm a dope. I didn't migrate passwords to the new file this error was happening in. I will say microsoft's error was pretty bad. I only realized because I re-enabled IMAP and that kicked a password error. 

Edited March 3, 20206 yr by MileFaker3000

I would strongly encourage you to start using the Office 365 APIs for this kind of integration.  I have a series of blog posts coming up that walk you through the setup.  These APIs are a lot more powerful than talking to the old-style protocols like SMTP, POP, IMAP,...

On 3/3/2020 at 8:27 AM, Wim Decorte said:

I would strongly encourage you to start using the Office 365 APIs for this kind of integration.  I have a series of blog posts coming up that walk you through the setup.  These APIs are a lot more powerful than talking to the old-style protocols like SMTP, POP, IMAP,...

Have the blog posts with this information been released?

https://www.soliantconsulting.com/blog/microsoft-graph-api-filemaker-one/

there's a second part to that as well that is also available there.

The error message:

530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM

generally indicates that Microsoft 365 rejected the SMTP connection because the client was not authenticated. This is usually related to the Microsoft 365 SMTP configuration rather than the migration or application itself.

A few things to check:

Verify that SMTP AUTH is enabled for the mailbox you're using.

Ensure you're connecting to the correct Microsoft 365 SMTP server (smtp.office365.com) and using port 587 with STARTTLS.

Confirm that valid Microsoft 365 credentials are being supplied by the application.

If Modern Authentication is enforced in your tenant, verify whether the application supports it or whether SMTP AUTH is still allowed for the account.

Review any Conditional Access or security policies that might be blocking SMTP authentication.

If authentication succeeds, the error should disappear. Based on the error message, it doesn't appear to be a migration issue but rather an SMTP authentication/configuration issue with Microsoft 365.

For mailbox migrations to Microsoft 365, I have used the EdbMails Office 365 Migration Tool, which connects using modern Microsoft 365 authentication methods and simplifies Exchange-to-Microsoft 365 migrations without requiring SMTP relay configuration.