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Flexible server monitoring

Introducing Simon 5!

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 4 gmail support?


I am trying Simon 4 and can't get gmail account to send a notifier. I looked at a post from 2008 that mentioned the same issues, which the poster was told to use simon to monitor the thread (funny, but still no updates).

Can someone verify if gmail outgoing through Simon works or not?

Here are the details I'm using:

Server name -
Port - 465
Email - (we are using gmail for our domain's email)
Password - Correct password used

No emails arriving.


David Sinclair's picture

Re: Simon 4 gmail support?


I don't use Gmail, so I can't give a definitive answer, but I gather you might have to turn on access for "less secure" apps?

I don't know if it matters, but you could also try using the server "" instead of what you have (though they may be synonyms for all I know).

Can anyone who uses Simon with Gmail provide more help?

Re: Simon 4 gmail support?

Hi David,

Thanks for taking the time to reply. What do you mean by "less secure"? I will try other outgoing server aliases, but I have already had success with - it's usually what is identified by default.

About to make a purchase for full software, but want to see the email feature work. What would you suggest?


David Sinclair's picture

Re: Simon 4 gmail support?

Here's a Gmail support page that explains the "less secure" option.

If that doesn't help, you could send from a different mail account, or use the Apple Mail transport.

Re: Simon 4 gmail support?

Yes, Google required less secure applications to access. Also, it was configured with