Category Archives: Mail

Email Encryption

Six Colors mentions that the GPG encryption author is running out of money. Now, like Dan Moren, I don’t have a whole lot of sympathy. That tool is a royal pain to install. I also think that Apple’s limited encryption (to and fro iCloud servers) is insufficient. What we want built into OSX/iOS is per file and per message encryption. Apple could write something like that and write a plugin or app for other services like Android. I think that’d make Apple a lot more attractive for many people and also drastically improve the state of mail on the internet.

Let’s be honest, mail started out as a trusted naive service largely within academic environments and never was designed for what it became. Yet changing the overall protocols hasn’t been successful. (Microsoft’s come closest with Outlook and Outlook server) Building something more secure on top of them is the way to go. GPG was a great idea with a poor implementation — largely due to the difficulty of putting it on most services. Having it ubiquitous requires someone like Apple stepping in.

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Set Recipient & Sender in Mail

Surprisingly Applescript in Mail has a ton of weird limitations that haven’t been addressed in years. For instance the only way to script much of anything in an active compose window is via GUI Scripting. The following quick script sets the recipient and sender of your message.1

I use this with a philosophy mailing list I belong to. For some reason the “reply to” fields aren’t set right by the listserv software. But if I type the name Apple mail will sometimes grab an old email address from the server.2 

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  1. Yes it’s a simple script. But I have readers who don’t do a lot of scripting who may find this helpful.
  2. I have the last 15 years of interesting messages from the listserv in my archives. Apple mail sometimes will autocomplete based upon the “from” of one of these old messages regardless of what I have in the Contacts app.


Gmail finally has a real API. Their old IMAP “API” sucked. Here’s hoping a new version of Mail for Yosemite uses this new API and Mail improves its connection to Gmail. (Although I’ve noticed Apple’s fixed most of my Gmail problems finally – I’m not even getting delayed messages anymore)

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