Am attempting to Send Mail with nMailMode = 0 AND .lUseSsl = .T. oSmtp = CREATEOBJECT("wwSmtp")

WITH oSmtp

.nMailMode = 0 && .NET

.lUseSsl = .T.

Am receiving an Error with ErrorLog:

2020.01.30 15:54:30:774 - --- Start Sending Email to west.exch092.serverdata.net:25

2020.01.30 15:54:30:912 - rec: 220 exch092.serverdata.net Microsoft ESMTP MAIL Service ready at Thu, 30 Jan 2020 12:54:30 -0800

2020.01.30 15:54:30:912 - snd: ehlo MBE-Jannys

2020.01.30 15:54:30:959 - rec: 250-exch092.serverdata.net Hello [38.125.33.226]

2020.01.30 15:54:30:975 - rec: 250-SIZE 52428800

2020.01.30 15:54:30:975 - rec: 250-PIPELINING

2020.01.30 15:54:30:990 - rec: 250-DSN

2020.01.30 15:54:30:990 - rec: 250-ENHANCEDSTATUSCODES

2020.01.30 15:54:31:006 - rec: 250-STARTTLS

2020.01.30 15:54:31:012 - rec: 250-AUTH GSSAPI NTLM

2020.01.30 15:54:31:012 - rec: 250-8BITMIME

2020.01.30 15:54:31:028 - rec: 250-BINARYMIME

2020.01.30 15:54:31:028 - rec: 250 CHUNKING

2020.01.30 15:54:31:044 - snd: auth login

2020.01.30 15:54:31:091 - rec: 504 5.7.4 Unrecognized authentication type

2020.01.30 15:54:31:091 - *** MAIL SENDING FAILED: 504 5.7.4 Unrecognized authentication type

The IT person is telling me: "It seems you are using Starttls . Try ssl tls"

Is there something else I need to configure?

Turns out this is an older Log File.

Have .LogFile Property specified but not seeing a new log file written. Am I missing something here?

This is the latest Error:

There's no log support for .NET Mode because the socket handling occurs inside of .NET. If you really need to monitor the connection you can use a tool like Wireshark. With WireShark you can monitor for specific protocols at the network level which is what you'd really want anyway to see the traffic from both ends. But also not terribly useful if you're using a secure connection because it won't decrypt the connection (might be possible with plug-ins though).

If you're seeing entries in the log you're not using .NET mode. lUseSSL doesn't work in non-.NET mode. So something is funky if you're having those log entries.

Make sure your username and password are correct and the SSL setting is what the server expects. In many cases you also need to specify a specfic port for SSL connections.

This is the best place to start: Sending SMTP Email

Make sure you set the username and password and set lUseSsl true.

+++ Rick ---

FWIW, just tried this myself again with my Google business acocunt and found I get the same error message as you. This is due to account restrictions for less secure applications not being allowed unless you enable that in your business account for that mail account you're using.

and:

I wouldn't recommend sending email through any of the free mail services - there are a lot of restrictions and rules and frequency limites that can get your account flagged for spam, which is really not what you want.

You can setup free mail accounts from companies like MailGun or SendGrid that specialize in sending messages via APIs (or using SMTP) and they have free plans that allow you to send quit a lot of messages without any charges.

+++ Rick ---

Thanks for getting back to me and clearing up the Log File issue Rick. As I stated after my initial post, the Log was for a previous instance when .Net mode was not used and should be ignored.

My last post displayed the 5.5.57 Error am now seeing.

Yes - I already rejected a proposal to setup a Google account for the very reasons you state. The Client's E-Mail provider is using Exchange - have successfully used WWIPStuff on Exchange and Office 365 Servers for years.

Marshal