I've spent most of the day trying to get the Gmail SMTP settings to work with this DNN site with no luck. Nothing works. I've tried smtp.gmail.com:587 and smtp.gmail.com:465 and smtp.gmail.com:25, all with and without SMTP SSL checked.

I've also cleared the cache and restarted the app pool. 

When I test the connection, this is the error I get: There has been an error trying to send the test email. The error is: There is a problem with the configuration of your SMTP Server. Mail was not sent. (no sh*t?!)

Yes, I'm sure the email credentials are valid.

It seems that Gmail is rejecting the DNN application. Even though I've activated the setting to allow other apps to use GMail, the SMTP test is still not working. Anyone know of another work around?

So I've gone through and created a web application in the Google API manager in hopes that it would help, but with no success.

Here's what the event log says:
AbsoluteURL:/Default.aspx
DefaultDataProvider:DotNetNuke.Data.SqlDataProvider, DotNetNuke
ExceptionGUID:3f66959c-34f5-4fe7-b9d9-ee39dd3b062f
AssemblyVersion:
PortalId:-1
UserId:-1
TabId:-1
RawUrl:
Referrer:
UserAgent:
ExceptionHash:Xs6omZylz6OyyvFDn2zToA==
Message:Failure sending mail.
StackTrace:
at System.Net.Mail.SmtpClient.Send(MailMessage message)
at DotNetNuke.Services.Mail.Mail.SendMailInternal(MailMessage mailMessage, String subject, String body, MailPriority priority, MailFormat bodyFormat, Encoding bodyEncoding, IEnumerable`1 attachments, String smtpServer, String smtpAuthentication, String smtpUsername, String smtpPassword, Boolean smtpEnableSSL)
InnerMessage:Unable to connect to the remote server
InnerStackTrace:
at System.Net.ServicePoint.GetConnection(PooledStream PooledStream, Object owner, Boolean async, IPAddress& address, Socket& abortSocket, Socket& abortSocket6)
at System.Net.PooledStream.Activate(Object owningObject, Boolean async, GeneralAsyncDelegate asyncCallback)
at System.Net.PooledStream.Activate(Object owningObject, GeneralAsyncDelegate asyncCallback)
at System.Net.ConnectionPool.GetConnection(Object owningObject, GeneralAsyncDelegate asyncCallback, Int32 creationTimeout)
at System.Net.Mail.SmtpConnection.GetConnection(ServicePoint servicePoint)
at System.Net.Mail.SmtpTransport.GetConnection(ServicePoint servicePoint)
at System.Net.Mail.SmtpClient.GetConnection()
at System.Net.Mail.SmtpClient.Send(MailMessage message)
Source:System
FileName:
FileLineNumber:0
FileColumnNumber:0
Method:
Server Name: WEB200

What makes NO sense is that the SMTP test works, but no info from a submitted form ever comes through. At this point I really don't know what more to do.