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Okay, i know that the built in SMTP server role inside Server 2008 is a little beleaguered; however, using resources here (stackex) and from msft I've worked through the issues I've been able to identify (SMTP wasnt generating logs, error message when looking at the current session view, IIS 6 compatability module, etc.) except for this last one (I hope):

When dropping email into the pickup directory, the SMTP service grabs it and moves it to the Queue directory where it sits for long periods of time (days? I dunno how long exactly since i kind of had my attention pulled elsewhere and then just noticed this morning that the mail items had finally be moved) before getting sent to the Badmail directory.

Weird thing 1: i have successfully sent mail using SSMS Database mail. Weird thing 2: i have successfully sent mail by logging into another intranet SMTP server via telnet and pounding out the fields (from, to, subject, body, etc.)

I'm guessing there is something I'm just overlooking with regard to relationship between my SMTP server and the intranet SMTP relays.

While not a novice, I'm admittedly more of a DB guy which is why I want this working, so that I can get SSRS to publish report subscriptions to various coworkers via email as opposed to having to create creds and making them login to retrieve the various reports.

Can anyone provide some insight?

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You can enable verbose logging to see what is happening, and can post that log here for assistance. So far though there's not much to go off of. Email sitting in queue can be for numerous reasons. BTW, why not relay the mail through Exchange? Or if you don't have Exchange, perhaps another mail server? I also recommend hMailServer over the built in SMTP. It simply is easier to setup and control and provides better logging. –  TheCleaner Jan 28 at 17:31
    
I have all the extended properties for logging enabled and can post some of the logs. Is there a verbose option besides the extended attributes without installing exchange? As per relaying through exchange, while i don't have exchange installed on this particular machine, I am more than open to using another server (like the one i mentioned in my initial post that i have successfully tested off of). Regarding hMailServer, i'm in a large corp, that is reluctant to install stuff they are unfamiliar with. I'd like to use available resources. –  ZenTechInc Jan 28 at 17:55
    
TheCleaner is right to suggest hMailServer. It's free and it's got way more features than the basic Windows Server SMTP server role. It will just make your life easier. That said, the mail item is sitting in the queue until it expires. More than likely, you haven't given the SMTP server a good route to use for the message. If your intranet has a relay server for outbound SMTP, you'll need to specify that as the default route. It's probably trying to send it out to the internet directly but being blocked by your firewall. Does the SMTP service stop itself all the time? Can you elaborate on the –  user2170433 Jan 28 at 18:30
    
I would just post the message transaction log info for a particular email that is getting stuck in queue. That should suffice. –  TheCleaner Jan 28 at 18:48
    
#Software: Microsoft Internet Information Services 7.0 #Version: 1.0 #Date: 2014-01-28 03:13:33 #Fields: date time c-ip cs-username s-sitename s-computername s-ip s-port cs-method cs-uri-stem cs-uri-query sc-status sc-win32-status sc-bytes cs-bytes time-taken cs-version cs-host cs(User-Agent) cs(Cookie) cs(Referer) 2014-01-28 03:13:33 10.233.198.14 OutboundConnectionResponse SMTPSVC1 compname1 - 7209061 - - 220+UTPPGATE01.cs.domain.com+ESMTP+Mon,+27+Jan+2014+20:13:33+-0700 0 0 69 0 0 SMTP - - - - –  ZenTechInc Jan 28 at 19:05

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