Internet Security Blog - Hackology

Email Issue Solved

Yeah… did it finally after a day of troubleshooting and testing…

The problem:

My ISPs SMTP server wasnt working perfectly resulting in mails not getting delivered !! Moreover, it was in the spam-list maintained by most of the mail services… which lead to the mails being delivered to the spam/junk folder !!

The solution:

Use GMail’s SMTP server to send mails 😛 it will surely be in the whitelist of the mail services… so sending mail using GMail’s SMTP server will resolve the issue !!

The detail:

I use Smart-Host feature on my SMTP server so that any mail being relayed through my server is forwarded to the 3rd party SMTP server and if that server is unable to send the mail… THEN my own server tries to send the mail…

GMail’s SMTP servers wanted TLS encrypted authentication… whereas the SMTP server I was using (MailEnable) didnt support TLS authentication 😡 😐 … I tested the MS SMTP (the SMTP service that ships with Windows Servers by default) and found out that it supported TLS authentication.

I started the MS SMTP service on another port (not going to tell you which one 😛 ) and placed this MS SMTP server of mine as a Smart-Host for my more feature-rich (but lacking TLS support) MailEnable SMTP server… AND for the MS SMTP server… I configured GMail’s SMTP server as the Smart-Host…

Now any mail relaying through my server comes to MailEnable SMTP server… gets forwarded to my MS SMTP server and then my MS SMTP server forwards the mail to GMail’s SMTP server after logging into it using the TLS encryption 😀

The only DRAWBACK :
GMail’s SMTP adds a ‘sender’ field in the mail header which mentions the username (GMail ID) used to log into their SMTP server…
The GMail inbox itself does not show the ‘sender’ field by default… but MS Outlook and Windows Live Mail (Hotmail) etc. reveal the “Sender” field in the “From” field like this

“From: [email protected] on behalf of [email protected]

GMail says that they are working on resolving this issue… so we are trusting them with this 😀 Hopefully that will be fixed soon !! For the time being… just be happy to get mails directly in your inbox instead of having to save “[email protected]” as your contact or ‘trusted’ ID 🙂

PS: This wasnt the easiest way to go… but I couldnt switch from MailEnable because the hosting panel my server is utilizing didnt support MS SMTP directly !! if you have any better solution please do let me know 🙂

PS2: HOLY SMOKES… that was lengthy 😛 that surely covers-up for my disappearance (I hope) 😀


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  • Good Job Fadi, it was bugging alot specially to the users of .::Hackology::. Portal which use to verify there email ID, with this now we are sure no one will be missing a mail ..
    I am sure no will find on behalf of note any troublesome , worth the cause.


  • ooh there was a problem with it that i forgot to tell you… remind me when you are back. have to discuss it 🙁

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