Back to iCloud for email

After a few months of messing around with various mail solutions (iRedMail, hosting my own osx server, open bad mail server, citadel, Zohomail, etc) I have decided its just too much work and am going back to OS X. I have decided that instead of finding a better way to manage all the e-mail I receive that I am going to start aggressively reducing the number of emails I get. No more mailing lists, unsubscribing from all newsletters, etc. E-mail is just not an adequate way of communication any longer because it’s overwhelming. For all communications that occur regularly via email I am going to request we migrate the conversation to Skype chat or via one of the other messaging services (if necessary, encrypted with OTR).

Over the month of June, I received an average of 182 emails a day, I hope to get this to 20 or less over the coming months.

OS X Server for email and contact sync

I have now been using OS X Servers + iRedMail on an old mac mini I had kicking around to handle my e-mail services. So far so good.

Some key points:

  • Unlike iCloud, unlimited server side email filters can be setup within iRedMail and these rules can be far more complex than iCloud allows.
  • Push e-mail works on the inbox and inbox only.
  • Contact, Calendar, and notes all sync without issue.

So far no issues whatsoever.


iCloud Max 99 Mail Rule Filters?!

So for the past year or so I’ve been using iCloud’s mail as my primary email. I enjoy using’s server side mail filtering (so that I don’t have to have a computer running the mail app in order to ensure my mail is filtered), today I hit the limit of 99 mail rules.

Not sure what i’m going to do…Guess a home brew mail server solution may be in the works.

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Privacy in 2014

For 2014 I’ve decided that I’m going to be much more security conscious.


A couple years ago in search of better push support on iDevices (eg iPhone), I switched from my self-hosted exchange solution to iCloud for all my email. I now have all my email addresses forwarded to iCloud.


  • E-mail is all stored (forever?) on Apple’s servers.
  • The Spam filtering sucks.
  • ‘Private’ e-mails are coming over iCloud and being archived with all my other mail (I archive my general mail).


  • Host e-mail on self-hosted (mac mini) Apple OSX Server. (All current e-mail will be forwarded).
  • PGP on all iDevices and laptops/computers.
  • S/MIME on all iDevices and laptops/computers.
  • (todo) Spam Filtering (potentially with DSPAM).
  • (todo) Setup a small encrypted mail server (Dovecot + postfix + DSPAM

Sync and Backup

Between photos, music, desktop backgrounds, application preferences, etc there is lots of stuff that needs to be sync’d these days. In the past I used a combination of many things including iCloud, DropBox, and bittorrentsync.


  • DropBox has size limitations (with free version…).
  • DropBox and iCloud are centralized.
  • Important files need to be backed up with some sort of versioning incase something is accidentally deleted or corrupted.
  • Sensitive files need to be encrypted and backed up.


  • iCloud sync for all non-sensitive application data (for any apps that support it).
  • BTSync for everything else.
    • Important and Sensitive documents will also be backed up to Synology NAS unit that does versioning incase of accidents. This also provides a fast mirror of all content.
    • Large aperture library will also be backed up to the NAS using BTSync.
    • Sensitive data encrypted with EncFS then Sync’d and backed up using BTSync.
    • Desktop backgrounds sync with BTSync.
  • Music and TV is stored on the Synology NAS and streamed via Subsonic (music), Plex (TV/Music), and Synology’s Audio/Video stations.
  • KyPass Companion (stored in iCloud) for syncing KeePass password database. (This also integrates with google chrome, I use it instead of google chrome’s password manager).


Best Practices:

  • Use a password manager, separate passwords for everything.
  • Use strong passwords (since you’re using a password manager, this shouldn’t make any difference when logging in since you’re not typing passwords anyways).
  • Downloads, Files in work, etc all go into sync’d directories now. Nothing should only be stored locally.
  • Media (Music/TV) should all be streamed, no more storing content locally.
  • Use PGP or SMIME as often as possible. Be careful with private keys (I store them in a TrueCrypt volume to make it easy to share between machines).
  • Do a clean install of OS X every now and again. Do it even more frequently if you’re downloading random stuff.

iCloud + Mail + Mountain Lion 10.8 + Mail Rule Syncing

Okay so it now appears that a new feature of Mountain Lion 10.8’s ability to Sync Documents & Data over iCloud also will sync your mail rules.

This could be a great thing because now instead of having to put in all my mail rules to (which is a laggy interface, and only allows for very simple rules (i.e. You cannot make an item as read when moving it to another folder).

The problem I predict with this is that since my laptop doesn’t run mail all the time, i’m going to have to keep mail running somewhere (not an issue, I have a Mountain Lion Server at home I can run a mail client 24/7 on), but what’s going to happen with my iPhone?

Is the mail going to come to the inbox and notify me prior to being moved to the other folders? Is the mail going to be moved instantly or is it only going to be moved once per minute when the mail app on my server polls (since as far as I can tell mail app on mountain lion doesn’t actually do real push email (or even true IMAP idle).

So I’m going to give it a try. Will update here when I’ve seen if it works out for me or not.

Project of the Day: A fully encrypted, non-logging, e-mail server based on Ubuntu + Amazon EC2

Recently I’ve decided to start taking email more seriously. Each day I send and receive dozens of emails, all of which sit around unencrypted on multiple devices. This is an issue as some of my email is sensitive. As such I’ve decided to at this two ways.

1) Easy, unsecure, synchronized, stored everywhere mail. 

For this I’ll use Apple’s iCloud. While it doesn’t work great at this time, it is an ideal solution to keep all the non-sensitive stuff synchronized between all devices.

2) Secure E-mail.

For secure e-mail I’m going to setup an Amazon EC2 instance. On this instance I’m going to be running NetBSD with an encrypted filesystem to store the mail

The primary means of accessing the mailstore on this machine is going to be via ‘pine’, a small, easy to use, text based email client.



<edit next day>

I ended up using netbsd instead of ubuntu. I’m using netbsd’s default email setup, then encrypting the home dirs (so that the email is stored encrypted), and using pine to access the email (so its easy to access and use).