Can mail notify/warn before sending?

Question

Level 1

8 points

Can mail notify/warn before sending?

My colleague keeps on sending emails to the wrong people (confidential emails!) and is getting in trouble.

Is there any way to change the mail app so that it pops up a notification like "are you sure you want to send?" or highlights the potential recipient in a dialogue box before he can actually send it?

I've tried looking at the mail rules but it seems you can only set rules for incoming mail, I've seen outlook can set delays/warnings which means he might have to swap to that.

Would be a great help if there was an alternative to Outlook 🙂 (he's running Yosemite FYI but could possibly upgrade him to El Capitan if needed)

MacBook Air, OS X Yosemite (10.10)

Posted on Mar 17, 2016 8:34 AM

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Answer 1

MrHoffman

Level 10

146,047 points

Mar 17, 2016 9:12 AM in response to Ace_Cream

Nope. Short of configuring and enabling and managing parental controls — and blocking everybody but approved recipients — not with Mail.app.

Likely won't help, though. If what's reported here is happening with mail, it's likely also happening with confidential materials and information releases through other means, as well. Warnings and prompts invariably get clicked through, too.

Your colleague has a choice of unlearning that habit of oversharing, or the choice of finding another job that better suits his habits, or he'll probably be provided an option for alternative employment from management. Or resolving whatever underlying medical condition might conceivably exist here, of course.

Or finding a mail client that is far more programmable than OS X Mail.app, and programming that to detect and reject sensitive materials.

Mail servers can be configured to drop or reject messages, but that involves some work on the mail server.

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Answer 2

Ace_Cream Author

Level 1

8 points

Mar 17, 2016 9:20 AM in response to MrHoffman

Ah I found something! Mailbutler. It's perfect for the job.

Every time he does it, he literally only realises his mistake as he clicks send or a second or two after. He was actually stuck holding down the send button earlier for about 10 mins as he didn't know what to do, it was hilarious.

So I've installed that add-on for mac mail and it gives him a 10 sec opportunity to undo the email if needs be, crisis averted!

Have to say the reply was a bit barbed hey? 😉 But no matter we have solved the problem! 🙂

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Answer 3

Mar 17, 2016 10:02 AM in response to MrHoffman

You echoed my thoughts.

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Answer 4

leroydouglas

Level 10

199,110 points

Mar 17, 2016 10:34 AM in response to Ace_Cream

Ace_Cream wrote:

Ah I found something! Mailbutler. It's perfect for the job.

Thanks Ace_Cream for posting your resolve.

This is the first I have heard of this plug-in: https://www.feingeist.io/mailbutler/

There is a good review here: https://www.macstories.net/reviews/mailbutler-adds-new-tools-to-apple-mail/

MacBook Pro (15-inch Mid 2012), OS X El Capitan(10.11.3), i7 480GB SSD 16GB RAM iPhone5 iOS9.2.1, Parallels10.0.2

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Answer 5

Kurt Lang

Level 9

68,596 points

Mar 17, 2016 10:35 AM in response to Ace_Cream

As MrHoffman already stated:

Warnings and prompts invariably get clicked through, too.

That little add-on will be ignored within a couple of weeks. Adding 10 seconds, a minute, or an hour delay won't change the basic problem - deciding if the mail should be sent as is before clicking Send.

I used to have a Post-It note on a heater switch right next to the UPS I have my Mac and other hardware plugged into. Big bright pink note to remind me to turn off the foot heating pad as I'm powering everything down for the day. Worked for about two weeks. I would then find the next day that I hadn't turned the pad off, despite a note being right where I can't miss seeing it. I had become conditioned to it being there and it no longer caught my attention.

The same thing will happen with a tool like this. It will grab the sender's attention for a while, then it will be ignored as it becomes background noise.

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