Comments on: Send Emails on Mac OS X with Postfix and a Gmail Relay

By: Chris

Chris — Mon, 23 Jan 2023 10:38:17 +0000

Thanks for sharing

By: Justin Silver

Justin Silver — Tue, 01 Nov 2022 06:47:21 +0000

In reply to Joe.

I haven’t tried them, but these seem to be the recommended upgrade paths – https://wpmailsmtp.com/gmail-less-secure-apps/. Good luck!

By: Joe

Joe — Sat, 06 Aug 2022 01:11:13 +0000

“Turn On Access for less secure apps in Gmail” is not available any more. Are there any alternatives?

By: Paul

Paul — Wed, 06 May 2020 01:53:11 +0000

Ok it’s a year or so old, but I’d like to add to Daniel (https://www.justinsilver.com/technology/osx/send-emails-mac-os-x-postfix-gmail-relay/#comment-2683) – reply isn’t working for me!
I got the same “the Postfix mail system is not running” error. But, if all you want to do is send email from your local machine (generated by cron or what have you) then this isn’t a problem. I’m sending mail fine from the mail command line. having Postfix not running will, from my understanding, just not let you receive mail, or other services of that nature. I’m not an expert, but I know that I’m on Catalina, and these instructions worked for me (albeit with the Not Working error) and I am now the happy recipient of cron job emails to my gmail account which is all I was needing.
Thanks Justin for documenting your set up.

By: Alex

Alex — Wed, 18 Mar 2020 10:08:33 +0000

This actually worked for me. Thanks!

By: Gilberto Conde

Gilberto Conde — Fri, 06 Dec 2019 22:25:00 +0000

Somewhere (https://apple.stackexchange.com/questions/229331/how-to-modify-a-launch-daemon-permanently-under-os-x-el-capitan) I also read that starting with El Capitan you have the SIP problem. The solution would be to put a copy of your daemon plist with a slightly different name (maybe adding local before the daemon name) in /Library/LaunchDaemons (instead of /System/Library/Lau..). Then you can make your edits. Ownership must be set to root:wheel, and permissions to 644. After disabling SIP, you should deactivate the original plist with `sudo launchctl unload -w /System/Library/LaunchDaemons/org.postfix.master.plist` and activate the new one with `sudo launchctl load /Library/LaunchDaemons/local.org.postfix.master.plist`. Don’t forget to reenable the SIP.

Well, I did all that in Catalina, but postfix is still not sending my message. I hope I don’t have a typo in my password or something as silly as that. 😀

By: Justin Silver

Justin Silver — Thu, 17 Oct 2019 15:47:50 +0000

In reply to Daniel Hinostroza. Hi Daniel - I set up Postfix way back when I made this post, and fwiw it is still running on Mojave on my machine (I have not updated to Catalina). I did just check the status and there is a note about "compatibility" mode, so perhaps this needs to be disabled in newer versions of the OS? My only suggestion is to try running postconf compatibility_level=2 followed by postfix reload to disable it. Good luck!

By: Daniel Hinostroza

Daniel Hinostroza — Wed, 16 Oct 2019 20:59:07 +0000

Hi,
I’ve done everything suggested in this post but I still get the message ‘the Postfix mail system is not running’. In some other page there was a recommendation to add a few parameters to /System/Library/LaunchDaemons/com.apple.postfix.master.plist namely, add:

RunAtLoad

KeepAlive

before
The problem is (I’m on MacOS Catalina) that the file is write protected and Terminal changes to /System/Library are restricted even with SIP disabled. So my question is: are these additions to com.apple.postfix.master.plist even necessary? or is the problem somewhere else?
All the very best,
Daniel

By: Tom Ootes

Tom Ootes — Tue, 09 Jul 2019 09:16:25 +0000

Total lifesaver! Thanks man.

By: Pavan

Pavan — Sat, 25 Aug 2018 11:11:21 +0000

Works perfectly !! Thanks