Exchange SQL Server 2008 Database Mail issue - sql-server-2008

Question

In my web application I have created a mail sender class and set the configurations of web.config file like this:
<mailSettings>
<smtp deliveryMethod="PickupDirectoryFromIis">
<network host="smtp.domain.com"
port="587"
userName="mail#domain.com"
password="password"/>
</smtp>
</mailSettings>
This is sending email. But SQL Server database mail can not send mail with the same account info.
Only one difference is PickupDirectoryFromIis .
Is there any setting on exchange server?
In the SQL Server Logs the errors are following.
Message
The mail could not be sent to the recipients because of the mail
server failure. (Sending Mail using Account 2 (2012-09-30T16:55:04).
Exception Message: Cannot send mails to mail server. (The SMTP server
requires a secure connection or the client was not authenticated. The
server response was: 5.7.1 Client was not authenticated).

Answer 1

Looks like this is a Authentication issue or port no issue.
Authentication Issue:
—————————-
Please make sure you have put the information as explained below:
Server name: smtp.gmail.com ( this is really important)
port no: 587 ( on many website this is given as 465 which is wrong, use 587 )
Check : This server requires a secure connection
Check Basic Authentication
username: youremailid#gmail.com ( should have gmail.com)
password: XXXXXXXXXXXXX
confirm password: confirm your password
Port No Issue:
——————–
Make sure port 587 is opened in your machine if you are following above example. If you are using any other port number (usually its port 25) to set up database mail in your office, make sure you speak with your security team and ask them to unblock port 25. Once they unblock port 25, your databasemail will work.
Network Connectivity:
—————————–
Also check network connectivity from your machine, if you can connect to internet from your machine on which you are testing your database mail. To test, do the following
Start- Run- type cmd – Hit Enter
Type ping gmail.com -t and then hit enter.
If output displays as Request timed out, it actually means there is network connectivity problem. Otherwise, your network connectivity is good.