MacOS – How to send smtp mail via gmail and osx Lion mailx

emailgmailmacossmtp

I would like to be able to send email from utility/batch/launchd scripts via my gmail account and the mailx client that is bundled in OS X Lion. I cannot find how to configure this. I found http://www.andrews-corner.org/mutt.html#sending which describes doing this for mutt, but I'd rather not have to install mutt. I do have Thunderbird installed and use that to read/send mail (instead of Mail.app).

When I run
mailx -v -s subject myemailaddress@gmail.com < file.txt
I get no errors, but instead of getting an SMTP transaction log, mailx tells me

Mail Delivery Status Report will be mailed to <David>.

Worse, there is no /var/mail/David folder, so this report appears to go into a bitbucket.

Best Answer

One way to fix this is to install the official server app in order to re-enable this feature. You don't have to setup a mail server through the app. Just installing it will allow use of mailx through the command line.

In the past, you had to buy and install OS X server as a separate product and now it's available from the App Store and gets installed on top of the normal OS.

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Macbook air mail: how to configure HELO sent to smtp server

(I apologize in advance for the wishy-washiness of this answer, but while I hope I'm on the right track, I do have some gaps in my knowledge.)

The SMTP HELO message, while something of a relic, is supposed to allow the client to identify itself to a server. It is still required for the protocol and is generally expected to at least be a syntactically valid hostname (which yours is not.) Your SMTP server appears to be complaining because it is indeed invalid.

Mail uses the name of your Mac, or the hostname assigned by the DHCP server on your network. DHCP servers don't always assign a hostname. OS X prefers a DHCP assigned hostname over using the computer's name as the hostname.

Based on this, the first place I'd look is my network configuration. I wonder, if you opened a terminal and typed hostname -f, what would you get? Possibly

$ hostname -f
mymac.mydomain\.co\.uk

If you do get this, the next step is to identify where it's coming from. A likely source could be a misconfigured DHCP server. You can try

$ sudo hostname mymac.mydomain.co.uk

to temporarily change the hostname for testing, or

$ sudo scutil --set HostName mymac.mydomain.co.uk

to set it permanently.

MacOS – How to setup Gmail SMTP server for OSX Mail with 2-step-verification and App-specific password

The SMTP server is used to send mail.

(Note: There are two locations you must paste you app-specific password, these instructions are for the 'sending' server, not the 'receiving' server')

Go to Google and generate an app-specific password on this page.

Now open Mail and go to Preferences > Accounts and select your Google account. At the bottom of the right hand pane it will say "Outgoing Server (SMTP):" and should have "Gmail" selected/ Click on this and you get a pop up menu and select "Edit SMTP Server List".

(This accounts area is where you paste in your 'recieving' password under 'incoming mail server'. Incoming server should be: imap.gmail.com, your username should be the start of your email address without the '@gmail.com' section and your password should be the app-specific password, NOT the account password that was previoulsy used)

This will open a list of the SMTP servers you have set up for sending mail. Click on the "Gmail" one and then click on "Advanced".

Set Authentication to "Password" enter your Google user name then the app-specific password you generated in the password field.

This should now work until you revoke the password.

Best Answer

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Macbook air mail: how to configure HELO sent to smtp server

MacOS – How to setup Gmail SMTP server for OSX Mail with 2-step-verification and App-specific password

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