Sending alert emails to other than smtp.gmail.com, specifically, smtp.comcast.net

[SmilingInSeattle]

First, I've searched these forums and think I could probably send my FreeNAS 9.1 alerts to smtp.gmail.com, but gmail is a secondary mail provider to me and I only poll it occasionally. I regularly poll mail.comcast.net.

The settings smtp.comcast.net wants are: port:587 and they've gotten pickier and pickier over the years. (I've all ready tried ports 25 and 465 from hints in forums). The only connection security I've been able to use with them from Thunderbird/Ubuntu 12.04 is STARTTLS, if available. Again, the only Authentication method that's worked for me is Password, transmitted insecurely.

STARTTLS is not available in the GUI.

I've double checked my gateway and DNS. Every GUI option I've tried has resulted in routing errors or connection unexpectedly closed.

I tried forwarding from my FreeNAS server to my local network desktop on to Comcast. Using sSMTP and POSTFIX I get errno 61 messages.

Is STARTTLS supported in /etc/local/msmtprc? Or is there an easier solution?

 

[jgreco]

You don't necessarily need to send your alerts to Gmail's SMTP server if you wish to use Gmail. Ditto Comcast.

However, "free" SMTP providers on the Internet may impose various restrictions, such as "you must use your e-mail address as the envelope From".

So you could probably point your outbound SMTP at smtp.gmail.com, using "smiling@gmail.com" (or whatever your gmail address is) as the "From" line in the SMTP settings, and whatever you need for authentication. You then have it use your Comcast address as the destination.

Not having a Comcast account, that's as much general help as I can provide.

 

[SmilingInSeattle]

After making this post, but before getting @jgreco's post I went ahead and set up FreeNAS 9.1.0 (which is old now) to send my alerts to gmail just as he mentioned. I'd previously set up my Gmail account to forward to the Comcast account I poll with Thunderbird every 6 minutes (as I had to create a Gmail account to access the Android "Play Store" anyway. I was pleased to see two daily status alerts (the daily run and daily security) in my local desktop mailbox when I awoke this morning.

My original goal was to set up a simple mail transfer of about 80 feet between my FreeNAS server and my desktop, which is running Linux thus saving a lot of bandwidth (not all of it mine, but nevertheless...) . However, I could never get the right parameters to get a successful message through, and I figured the only way I could receive the mail was to set up one more "Account" under Thunderbird. So next best would have been to send directly to Comcast where I have an account.

While I'm now successful with getting alerts to my desktop, I'd still like to get to my original quest. I'm comfortable with editing configuration files. Having ASCIIi configuration files is one of the greatest reasons (of about 20) why I like UNIX variants. BAck in the mid '90's I was a fan of OS/2 primarily because there were registry editors and people wrote documentation that went along with them that made the entries make sense. I still dabble with OS/2 in a VM when I'm in an experimental mood.

Anyway, if there's an MTA guru browsing through these forums, I'd sure appreciate a "shout." If you want to verify what Comcast wants to access their SMTP servers, Google "Comcast SMTP Linux" and/or replace "Linux" with "Ubuntu." You'll not get much out of Comcast's support as they unabashedly only support Windows (and their mail handlers) and "dabble" in iOS.

 

[jgreco]

MTA guru, right here.

Except this is more of a MUA issue (MTA being communications between two mail servers, MUA being stuff like user submission). I hate MUA stuff because there are so many fine ways for providers to creatively implement brokenness. And since we operate our own mail servers here, well, local policy is not to do nasty things and support as many options as reasonably possible to allow maximal user happiness.

So along those lines, clarify:

1) Are you on a residential or otherwise dynamic IP address that would be likely to be listed as "dynamic" by your service provider, and/or have outbound port 25 blocked? Because if not, you could also possibly have the FreeNAS box try delivery to your mail provider's inbound MX (pretending to be MTA-MTA communications). This has the downside of being fragile in the future.

2) What's the story with your desktop? Is it running an MTA? UNIX can usually run a local MTA without issue, and it is often easier than trying to bludgeon together a solution involving someone else's mail server (where combating spam is at direct odds with your simple desire to receive cron mail). Yes it would be another account under Thunderbird.

 

[SmilingInSeattle]

I'm on a residential (or dynamic IP address) and use the old (standby) internal Class C network of 192.168.1.0. The outside world comes in via a dynamic address (although it's pretty static in that I have a commercial account). The ouside world is then NATted to my local account by the cable modem where it goes into a wireless and wired router. I have about 10 static routes using cascaded switches as well as serve up to about four wireless devices and a secondart wireless access point (via hard wire). I'd like to have the FreeNAS box send its messages directly (through the switch with/or without the DNS imput of the router) to my Ubuntu desktop.

The Ubuntu distro is supposed to directly support sendmail; however, I think I kind of screwed that up by installing ssmtp (which then made a soft link from /usr/sbin/sendmail to /usr/sbin/ssmtp. When that setup didn't work, I uninstalled ssmtp which also seemed to delete the sendmail binary. I did that at the time I installed postfix, which as I read "looks like sendmail but doesn't work like sendmail" Postfix has now also been deleted. So, at this time, there is no sendmail binary (although that should be easy to remedy)

My current mail client is Thunderbird 24.0; however, I'd been relying on Comcast to be my MTA. A long time ago I (about 1996) I ran an OS/2 MTA just for my desktop at work. It was more an experiment in how an MTA runs as I found it was a "Pain" to keep up with configurations, and since it was a working (meaning real work) computer, it didn't look good if I was unable to see or reply to me e-mails! It's interesting that you say it's easier to put together than using someone else' Obviously, as Comcast runs just a POP3 server, I'd then want to get into an IMAP server, but then I'd want outside access to the IMAP server on my desktop and then would be all involved in firewalls, DMZ and possibly VNC issues. At 68 years young, it's interesting, but there are also other things I'd like to do as I'm still working too - graveyard shift I might add, keeping the gamers machines working!