Database Mail using External SMTPs #fail

It is Saturday morning.  The teenagers are fed.  I made pancakes, added blueberries to my own, and since I am on a health kick this year too, I only topped mine with applesauce, but somehow they still added up to nearly 1100 calories. (holy crap!).  They got the melted butter and syrup on oven-warmed plates.   I even cleaned the entire mess up and washed the dishes, so my wife is happy too.  With a belly full of blueberry pancakes and a fresh pot of peppermint mocha coffee I have about two hours to blog before the droopies set in and my mind turns to mush from carb overload, or the honey-do list is presented for immediate service.

Today's task will be to install Database Mail.  For those of us who are new to SQL, there used to be SQL mail, it was dependent on Exchange or some other MAPI system.  You may run into that in older instances, but for my purposes, I really want to move forward, so that's it on that.

You still need to have an SMTP server though.  So, if you are like me running servers that are going to go away in a couple months, you want to do so for FREE, and on a permanent server if possible.  (I love free; my wife usually agrees that I can afford it).   To the GOOGLE:>> insert batman trumpets>>  "Free SMTP Server"   And there it is - "How to use Gmail as your SMTP server".     Somehow, keeping my server clean of this service appeals to me.  

http://lifehacker.com/111166/how-to-use-gmail-as-your-smtp-server

I see a couple caveats in my first perusal of the instructions here: if your network "lets you connect to an outside SMTP server"; this one could bite us.   The second they mention is that the reply is overridden, but we are not going to send mail back to an alert, so this is no problem.   Update 3 is interesting for our purposes too.  If we set up an email specifically for this purpose, we can use that account name or set a different default, like DBALERT or something.  Hmmm.

Sidenote:

http://www.softstack.com/freesmtp.html

Has a few possibles individual servers, each appears that it would need to be installed.  This is not an endorsement of any of them, just a note that if you spend more than the 2 minutes I have, you will probably find one that suits your needs; I have only clicked on the first three links.  Maybe I'll install a few on the VPC side, which will install and then go away immediately and perhaps blog on this again in the future.  It sucks to be curious about everything - Let's stay focused on SQL.  

Yep.  Indeed that was too easy.  Failed on every try, even with the corrected ports; probably the TLS limitation that I don't see intuitively how to set.  Normally, I make things more complicated than they are.  But when it seems to easy, it probably is.  

We'll have to do this by the book.