Emailing PDF's when dropped into a folder

Hi all,

New here. Sorry if I’m not familiar with the etiquette. Just going to drive straight in.

My issue is do about a hundred of these emails every Friday
I send emails of pdf’s to a specific account: with the subject “Results Completed - File_name”

I was hoping to make something that does this to me automatically:
drop files “alphabet soup 22Nov2020.pdf” into “HD\users\username\desktop\Send” folder
Triggers the automator:

  1. Email file to with the subject “Results Completed - alphabet soup 22Nov2020” (with or w/o the *.pdf)
  2. Move the file from “HD\users\username\desktop\Send” to “HD\users\username\desktop\Sent” folder

So i can just collect these pdf’s and then drop them into that folder. This task literally takes me 5 hours every Friday.

  • Do you use Hazel or Keyboard Maestro?
  • Do you have an existing Automator automation for the e-mailing?
  • Are you using Apple Mail for e-mailing, and do you need to use that?
  • Are you familiar with AppleScript or any shell scripting?
  • Is there a reason to send 500 mails with the specific subject line to this address rather than 1 mail with details of 500 files?
  • The sending of the file appears to be optional. What would be the preference and why?

I’m wondering if you just really need a shell script to generate and send 500 mails (with appropriate anti-spam pausing if required) by looping over the set of PDF files modified that day in the final folder?

I don’t know if can be automated this way, but I do know that if you were able to use MailMate, this literally could be a shell script that would mail the PDFs and then move them.

My biggest concern would be, as sylumer alluded to, that your SMTP server would consider it spam if you were sending them as fast as the script would be able to do it. But we could also build-in a delay in-between each one.

Here’s what I came up with:

There’s a command line mail utility in macOS called mail. It is very useful for automatically mailing logs and posting to things like Evernote that have a mail gateway all from a shell script, independently of whatever GUI mail app you may have.

However my mail client of choice on macOS is also Mailmate. :wink: