Encrypted Email Support for the iPhone with iOS 5

Back in November, we took a look at what it takes to encrypt email on the Mac using Apple Mail.  If you are the user of an iPhone, iPod Touch, or iPad, and checking your email on that iOS device while sometimes sending encrypted email from your Mac, you will find that you have a problem.  The certificate used to encrypt outgoing mail and decrypt incoming mail is stored on the Mac and is not installed on the iOS device by default.  Oddly, Apple engineers have not seen fit to make the certificate files part of the information that is synchronized between the computer and the mobile device.  But, not to worry.  With the release of iOS5, email encryption is now supported.  You just have to know the tricks necessary to get the certificate installed and the iOS configured to use the certificate.  As it stands now, iOS encrypted email support is technically functional.  Its just not smoothly implemented or what I would describe as "up to typical Apple standards."

We start by assuming that you have already implemented encrypted email on your desktop/laptop Mac OS computer.  If you have not, check out this post for the details explaining everything you need to know.  The steps detailed below assume that you have the email encryption certificate installed and working on OS X as you will need to export some of that information in order to install it into the iOS based device.

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Send and Receive Encrypted Email with Apple Mail

With the release of OS X 10.7, Apple engineers brought a serious update to Apple Mail.  When this happened I was finally able to cast Microsoft Outlook (formerly Microsoft Encourage) aside.  Encourage was functional but slow.  But when it was deprecated in favor of Outlook things went sideways.  Microsoft went for a complete rewrite of the codebase and in doing so introduced significant issues into the product, many of which they have yet to fully resolve.  So when Apple Mail turned out to be a truly impressive update, I made the switch and have not regretted the change.

One of my larger issues with Encourage and Outlook was their support for encrypted email.  It worked, in the technical sense, but it never worked well… at least in my opinion.  Conversely, Apple Mail just works.  No qualification necessary, no messing around.  It just works.  The only tricky part is the initial configuration.  Here we will configure Apple Mail (version 5.1 that is part of OS X 10.7.1) to send encrypted messages...

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iPhone and iPad iOS 5 Wi-Fi Auto Sync Disabled

This is an issue that will likely only affect a small number of users.  But since it was an problem for me, it worth a post to explain the fix.

One of the great new features of iOS 5 is the ability to sync with iTunes over Wi-Fi and eliminate the need to plug the iOS device directly into the computer in order to backup and update software, content and playlists.  To enable this feature, first plug the device into the computer via USB.  When it appears in the Devices list on the left side of the main iTunes window simply click once in your devices icon.  Then select Summary from the top of the main window on the right.

Scrolling to the bottom of the main window, there is a section labeled Options.  Be sure to select the box labeled Sync this Device over Wi-Fi.  Until that box is checked, the iOS device will not sync over Wi-Fi.  If the box was already checked by default, you’re set.  But if you had to check it yourself, be sure to click the Sync button in the lower right hand corner of the window.  This insures that the settings take effect.

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Mac OS X 10.7.2 iChat Stops Working with AOL Instant Messenger Logins

When Apple released Mac OS X 10.7.2 yesterday, a wide set of new features were made public.  Many of these included support for the long awaited iCloud.  But in the process, Apple managed to break iChat’s support for AIM (AOL Instant Messenger) logins in some cases.  So, if you launch iChat and some of your buddies are missing, or you see a small message in the buddy list showing AIM is disconnected, you are one of the effected.

Fortunately there is an easy fix.  From in iChat, select Preferences from the iChat menu.  Then click on the Accounts button at the top of the window.  Click once on your AIM account in the list on the left and then click on the Server Settings tab at the right.  Odds are your Server field is currently listed as api.oscar.aol.com.  Apparently this server address no longer works if the Use SSL check box has been selected...

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Parallels Desktop 7 Full Screen on Mac OS X 10.7 Lion

I feel compelled to post this because I know there is someone else out there going through what I have, and I hope to save you the frustration.  When Apple released OS 10.7, one of the new features was full screen support for applications.  Just click the small widget in the corner of the window and the application window expands to take over the entire screen.  And if your Mac has more than one monitor attached to it, that application takes over all attached displays.

This is useful in some cases.  But this is 100% counterproductive for me when I am using Parallels Desktop to run Windows on my Mac.  The goal was to put Windows full screen on my second display and then continue to run all of my Mac applications on the primary display.  This way I would have access to the Windows and Mac environments without switching virtual desktops (which is essentially what happens when an app is in full screen mode).

When Parallels upgraded Parallels Desktop to version 7, they brought all of the 10.7 Lion goodness to the product… including Lion’s “improved” full screen support.  The problem was that this full screen support murdered my daily workflow and forced me to start running Windows inside a window rather than full screen on my 2nd display...

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