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Simon version 5 is now available. It is a massive update, introducing a much-requested feature: syncing the Simon data between multiple Macs, plus a Simon Status service, a Link Checker filter, improved Find filter, iMessage and Speak Error notifiers, a new app icon, and much more.

Important: please note that Simon 5 requires a minimum of macOS 10.12 (Sierra), and is a paid upgrade from Simon 4. Purchasers since September 1, 2020 automatically get a version 5 license (that also works in previous versions).

Read the Simon What's New page for details.

Simon Notifier's Not Working

Looking for some troubleshooting assistance with the notifiers.

So about 3 months ago Simon stopped sending emails to us ... I wasn't sure what changed, but I figured it was something with the computer. So I ran a simple test and opened Apple Mail and sent out an email from there and the email sent out just fine. At this point I figured something with Simon and since I was planning on upgrading from Mavericks with Simon 3.xx to El Capitan running Simon 4 soon, I figured I'd wait and start completely fresh.

Well, that's done.

I formatted the HDD and installed a fresh copy of OS X 10.11.3 and then I installed Simon 4.1.1 and I didn't import over ANY files whatsoever. Everything is setup fresh, by hand.

Low and behold, exact same issue!

Without this becoming a wall of text, I'll try to explain my troubleshooting techniques thus far:
I first opened Terminal and issued the following commands:

Subject: This is a test from terminal

This is the content of the message.

This shows up in the mail.log file:
Jan 29 15:27:38 Simon-Offsite postfix/smtp[9727]: 6E9EEA332A: to=, relay=none, delay=168, delays=17/0.02/151/0, dsn=4.4.1, status=deferred (connect to[]:25: Operation timed out)

All right, I figured this is probably happening because the of the Internet Service Provider not allowing sending without authentication.

So then I tried Apple Mail, setup an account (same settings as what I use in Simon), and works, no problem.

SO then I tried having Simon using Apple Mail. Notify Now ⌘K still doesn't work, but then out of no where I got a Recovery email on one of my tests that I set up. I looked at Apple Mail Sent Items and sure enough it's in there. Why did that work but Notify Now ⌘K not? Either way, this isn't what I want, I want Simon to be it's own service and not rely on another program.

So I setup another mail server of which I can view the logs on. I click Notify Now ⌘K .... nothing Simon doesn't even attempt to connect to the mail server to even log on. So then (thinking maybe Notify Now ⌘K is completely broken in Simon 4.1.1) I try making a test fail since I got an email from that the last time when using Apple Mail. Again, nothing at all.

So I went to the firewall on the network with the mail server and looked for packets coming in from this Simon machine ... nothing at all is coming to my network.

Is DNS working?

Terminal command: host has address

It's right.

So my question here is, is there a log that Simon writes to for emails that it attempts to send?

I'd like to see if Simon is running into an error with the network / ISP / whatever.

Or other, if the idea is present, are there other things I could try / test to eliminate?

Thanks for any help possible.

David Sinclair's picture

Re: Simon Notifier's Not Working

I'm sorry you're having difficulties with mail. It can be tricky at times.

Simon does write some diagnostics to the Console log, so that might provide a clue.

Try running Simon 4.2b1. It includes some improvements in the email notifier.

Using Notify Now is definitely helpful to check that it's working; well done for using that.

oranges2apples's picture

Re: Simon Notifier's Not Working

Do you know where in the console log?

I'd love to see an error of some kind, somewhere.

system.log didn't show anything at all, and neither did the All Messages area. Was hoping that Simon had it's own log somewhere that would write back messages from the Notifiers.

oranges2apples's picture

Re: Simon Notifier's Not Working

Kidding! Saw something finally.

I'm becoming more and more convinced that Notify Now ⌘K is not working at all. Can you confirm?

When I force a test to fail or recover I get the following error:

2/1/16 2:09:24.591 PM DejalMailHelper[3124]: service Error sending email: Error Domain=MCOErrorDomain Code=1 "A stable connection to the server could not be established." UserInfo={NSLocalizedDescription=A stable connection to the server could not be established.}

Finally, an error to work with, unless this right away means something to you, I'm gonna start searching around for answers on this error. I can't tell if that error is in reference to DNS or Internet connectivity or what at this time.

David Sinclair's picture

Re: Simon Notifier's Not Working

I'm not sure what that error means in this context (it comes from the mail framework I use). But yes, it sounds like a DNS or connectivity issue with your mail server.

You could try adding a test with the Email Cycle service, to see if that could provide any clues.

I just tried Notify Now with one of my email notifiers, and it worked as expected.

oranges2apples's picture

Re: Simon Notifier's Not Working

So I found a lot of information surrounding MailCore online when looking up that error. Most I saw with this error was with no solutions ever found.

I did find 1 post however that stated that they resolved the problem by implementing the STARTTLS code into their MailCore code. Though it didn't appear relevant to my situation at first glance, I read over your released notes and that was one of the things you noted adding. Could there be a correlation? Doubtful, I thought, since we don't even use STARTTLS, I just use TLS.

However, based on your recommendation and for the sake of trying it, I reluctantly stuck the beta software on the computer just to check it out (I'd rather not run beta software basically on this particular machine).

Everything now, including the Notify Now ⌘K, works as expected without me needing to change anything with the settings!

So firstly, I can't wait for 4.2 to get out of beta.

This started happening like 3 months back or so. Our ISP merged around then and so their rules or mail servers may now enforce more strict rules, but can't imagine Simon not being able to handle that, though Apple Mail was able to send email just find whereas Simon could not.

And whether or not the issue was fixed by the addition of the STARTTLS support or not is really not terribly important (btw I'm using the SSL/TLS option, not STARTTLS). What's important is that whatever was changed between 4.1.1 and 4.2 made all of my notifiers work again like they used to.

Thank you for the recommendation David.

David Sinclair's picture

Re: Simon Notifier's Not Working

Excellent; I'm glad 4.2 solved the problem.

It is basically ready for general release; I'm only waiting for some localization updates, and don't plan to make any more changes for this version. So you should feel confident using it.

oranges2apples's picture

Re: Simon Notifier's Not Working

Since it's still a beta, the Notify Now and Stop Check menu option doesn't seem to update well. Not sure if you could make that better.

Basically, on a failed email, it doesn't show the preview at all and just sits there saying Stop Check the whole time. I click on Stop Check and it still says Stop Check.

Ideally when you click the Stop Check menu option, it would change to Check Now or whatever and let you tell it when to try again.

It's a bit weird, selecting the Notifier seems to instantly do a Check Now, which I feel wouldn't be a desired action until specifically invoked by the user.

I selected a notifier and went to edit it and during the entire time I'm not sure if it's sending an email with my new changes or my old changes.

Anyways, just things that I though was a bit wonky ... buggy. FYI. Maybe it's all done by design, in which case, no problem, I'll adapt!

oranges2apples's picture

Re: Simon Notifier's Not Working

To add, I should mention, every time I click Stop Check, it actually performs a check and sends another email...

David Sinclair's picture

Re: Simon Notifier's Not Working

Showing the preview automatically when you have the Preview page displayed is by design. Though I agree that while that makes sense for tests, maybe it shouldn't for notifiers, since they have more of an effect. I'll think about that.

I have noticed the icon get stuck on the Stop mode on occasion, but haven't noticed a pattern to it.

oranges2apples's picture

Re: Simon Notifier's Not Working

No, I do like the previewing of the email. It's just that it only shows upon a success.

If the email fails, nothing happens in preview ... which, by design, I think is fine. Though, an error message here might be nice if, let's say, "can't authenticate" or whatever. Though, based on the fact that this pane is for a preview ... might not quite make sense.

Either way, I like the preview, it's just that it seems to get "stuck" when the notifiers don't work successfully.

The Check Now / Stop Check menu option definitely get's all "wonky" when the notifier doesn't complete successfully. Put in the wrong credentials on an Email notifier and it should happen 100% of the time ... there's just no way to stop the test. And again, simply selecting (single-clicking) on an email notifier, immediately performs a check now, which would be nice if it didn't until I tell it to.

David Sinclair's picture

Re: Simon Notifier's Not Working

I agree it'd be better if an error is displayed in the preview. I'll see if that's feasible.