Email Troubleshooting

Is there anyway to get the email logs of what sent and what failed and why? I get some of the emails but it doesn't seem to want to send to my gmail account but I get it all the email alerts on my domain accounts.

I also got this issue right after I created a issue and attempted to send it to my gmail account. Dont know if its related might have just been a permissions thing in IIS.

Type: Errors
Severity: Error Error
Date: 3/8/2015 9:49 am
Message: Unhandled phpmailerException: SMTP connect() failed. in C:\inetpub\wwwroot\webissues\system\mail\class.phpmailer.php on line 1169
Stack trace:
#0 C:\inetpub\wwwroot\webissues\system\mail\class.phpmailer.php(1020): PHPMailer->smtpSend('Date: Sun, 8 Ma...', '...')
#1 C:\inetpub\wwwroot\webissues\system\mail\class.phpmailer.php(928): PHPMailer->postSend()
#2 C:\inetpub\wwwroot\webissues\system\mail\engine.inc.php(153): PHPMailer->send()
#3 C:\inetpub\wwwroot\webissues\cron\job.php(172): System_Mail_Engine->send('jbpollard@chesa...', 'jb pollard', 'Patient First -...', '...')
#4 C:\inetpub\wwwroot\webissues\cron\job.php(72): Cron_Job->sendNotificationEmails()
#5 C:\inetpub\wwwroot\webissues\system\core\application.inc.php(210): Cron_Job->execute()
#6 C:\inetpub\wwwroot\webissues\system\bootstrap.inc.php(130): System_Core_Application->run()
#7 C:\inetpub\wwwroot\webissues\cron\job.php(690): System_Bootstrap::run('Cron_Job')
#8 {main}
User name: jb pollard
Host name: 127.0.0.1