Exchange Nivana in Snow Leopard?

I have written a few posts on how I use my Mac and iPhone to interact with an Exchange server for calendaring and contacts.  I have tried Snerdware Groupcal and AddressX until it was not available for Leopard (Ok, but not great).  I then tried the MS Entourage sync prior to the iPhone 2.0 software (Not great, had problems with duplicates and lost entries).  So I am still searching.  What I have found that works best is to use Apple Mail for mail, Entrouage for calendaring and the ActiveSync features of iPhone 2.0.  I have not had any problems with this setup to date.  This solution works well, but is not 100% Apple native.

AppleInsider recently ran a story called Apple’s Snow Leopard to sport Cocoa Finder and ImageBoot.  In this article is a blurb about MS Exchange integration with iCal and Address Book.

Microsoft Exchange Support

Other advances are also present in the new test software, such as broader support for Microsoft Exchange 2007 in Snow Leopard’s versions of iCal, Address Book and Mail. The implementation of Exchange support remains a work in progress, according to those familiar with the matter. As such, Apple has reportedly asked that developers focus their testing efforts on a subset of Exchange capabilities, such as scheduling events in iCal, adding contacts to Address Book 5.0, and automated account configuration in Mail.

It looks like Apple is really trying to reach the corporate crowd with these advances.  Good for me, good for Mike N (transitively good for Paul B), good for all!

Beer Goggles for Mail

What a concept!  Ever hear of “drunk dialing”?  Ever call an ex after a night of drinking? That was so 1985.  This is 2008 and we communicate with e-mail, twitter and SMS.  Google just protected us from regretting a drunk e-mail by deploying Mail Googles:

Sometimes I send messages I shouldn’t send. Like the time I told that girl I had a crush on her over text message. Or the time I sent that late night email to my ex-girlfriend that we should get back together. Gmail can’t always prevent you from sending messages you might later regret, but today we’re launching a new Labs feature I wrote called Mail Goggles which may help.

When you enable Mail Goggles, it will check that you’re really sure you want to send that late night Friday email. And what better way to check than by making you solve a few simple math problems after you click send to verify you’re in the right state of mind?

Twitter and cell phones need to put in some “Tweet Goggles” and “Text Goggles”.

Freedom from the chains of sync

My organization runs Microsoft Exchange as their primary e-mail and calendaring platform. Up until recently, there really has not been a very good native Exchange client for mail or calendaring. I have been using Apple Mail for quite some time to connect to Exchange for mail (see Inbox Nil and the Mail Ninja, Part I Setup) and have no plans on switching to a different client. However, the lack of a good calendaring client has forced me to use Outlook through Parallels or VMware Fusion to interact with our shared calendars.

Under Tiger, I used GroupCal to sync my iCal with Exchange. This worked somewhat well, but GroupCal is NOT yet ported to Leopard. I have been using a kludge since upgrading to Leopard that does the job with a bunch of caveats (See Leopard: Archive and Install (Post-Install Comments)). But I finally have an answer!

On Friday I received a copy of MS Office 2008 for Mac. The Entourage Exchange client is much improved. I do not plan on using it for my mail or calendaring client, but it does provide an Intel version that is able to sync my Exchange information to iCal and Address Book. I tried this with the previous, non-Intel, version of MS Office for Mac with very little success. The sync daemon would either hang, crash or cause my CPU to spike badly.

Although I have only been running Entourage 2008 for a few days, the results are very promising. I am able to accept, decline and update calendar invites through iCal. These calendar entries show up immediately in iCal and within a minute or two show in my Entrouage and Exchange calendars. I then sync’ed my iCal “Entourage” calendar with my iPhone without issue. So far, so good. I am keeping my fingers crossed.

The final piece of the puzzle is free and busy time. I have two options for this, use Entourage to schedule a complex meeting OR subscribe to individual calendars that are published on Google Calendar or .mac. I am thinking a hybrid approach will probably be the solution. I plan to publish my calendar on my .mac account.

So in a nutshell, I installed Office 2008 to sync my contacts and calendar. I have not used MS Office for Mac for over 5 months and have been very happy with NeoOffice and iWork. The Entourage client is much improved, but I still enjoy the simple and clean interface of Apple Mail and iCal.

Microsoft’s mactopia has a nice HOWTO on the process: Synchronize Entourage with an iPod or iPhone.

Inbox Nil and the Mail Ninja, Part IIIb Theory

Taking the approach found in my last Inbox Nil post has forced me to search my mail file more often than before and more effectively. I have yet to encounter a historical message that I could not find, and this approach seems quicker than looking through a folder diverse hierarchy. There are two Apple articles that have been helpful when trying to create a complex search. I hope to consolidate all of the Mail and Spotlight advanced search options in a future post. I really could not find a one stop spot on the web for Mac OS X searching.

• Mail 2.0 Help: Searching your email
  
• Apple – Mac OS X – Tips – Spotlight

The final Mail related change that I made was archiving anything older than one year. I created a Smart Folder that finds messages older than one year regardless of folder location. I then put these messages into an archive folder. My backend mail system is Exchange, so I then use Outlook to create PST files for archive purposes. I am sure there is a better way, but for now, it is working. Boy it would be nice if Apple Mail could read PST files!

There were a few other nuggets of productivity that Merlin’s talk gave to me. I now use NetNewsWire Lite to read my RSS feeds instead of Safari. I found myself being distracted by new RSS articles when trying to browse for more important items. Now I read my RSS feeds once a day without distraction (or distracting me from real work).  I also try to only read my mail once per hour.

I have been using these techniques for a few of weeks now. I am reading and following-up on e-mail more effectively and have been able to track down, via a search, historical messages without problem.

Inbox Nil and the Mail Ninja, Part IIIa Theory

I have drastically changed my way of interacting and filing e-mail. In the past, I created a folder for every customer, company, project, etc which yielded 100+ folders. To keep everything in order, I would manually move messages to folders or create Mail ActOn rules. I felt like I was filing all day long.

I have been a follower of the Inbox Zero philosophy of Merlin Mann. Inbox Zero is a “series looking at the skills, tools, and attitude needed to empty your email inbox — and then keep it that way.” In order to keep my inbox at zero, I frantically filed and flagged message all day long. I really did not grasp the concept until I listened to Merlin talk about Inbox Zero at a Google Tech Talk session.

After listening to this talk, I starting thinking about how I can make reading and filing e-mail more efficient. I made a leap of faith to rely on Mail.app’s and Spotlight’s search capabilities to find messages and started generalizing my folders and filing. I also felt that I needed to rely on some of the capabilities of MailTags in conjunction with Smart Folders to categorize important items.

I have taken my 100+ folders and 25+ Mail ActOn rules and condensed them to 5 folders and 5 Mail ActOn rules. I have also created a handful of Mail ActOn rules to MailTag messages with tags such as:

• Clear All Tags
• Flag Next Action
• Flag Read Later
• Flag Waiting For

I have created Smart Folders to give me views of my MailTags (Next Action, Read Later, Waiting For). My ultimate plan is to also MailTag projects and create associated Smart Folders for “one off” type projects.

Inbox Nil and the Mail Ninja, Part II Add-ons

Apple’s Mail.app is feature friendly and very robust, however there are a few add-ons or plug-ins that really boost Mail’s functionality.  And interestingly enough, some of the add-on functionality provided by plug-ins are being integrated in to Leopard’s Mail upgrade.

I currently have the following plug-ins installed and use their functionality daily:

• Mail ActOn (free) – combines keystrokes with rules to easily file, tag or perform some action on a message.
• MailTags 2.0 ($29.95) – allows messages to be tagged, annotated, or added to iCal as an event or todo item.
• Lettebox (free) – rearranges the interface into three vertical columns.

I will go into a deeper discussion on how I use these addon’s to interact with smart mailboxes and daily email processing to boost productivity and adhere to a GTD-style processing of my Inbox.

For a complete list of Apple Mail plug-ins and add-ons, see Hawk Wings: Plug-ins and add-ons list.

Inbox Nil and the Mail Ninja, Part I Setup

Apple’s Mail.app is a very easy to use, intelligent and non-obtrusive E-mail application. Apple improves Mail.app’s functionality with each release of their OS. I am very excited to use some of the new features promised in Leopard (OS X 10.5).

I use Apple Mail to connect to my organization’s Microsoft Exchange server as well as my .Mac account. Mail supports connecting to MS Exchange as an option when adding a new account, however under the covers it is making an IMAP connection to Exchange. If you plan to connect to Exchange, contact your administrators to make sure the proper ports are enabled both in Exchange and your organization’s firewall. I would suggest using ONLY the SSL enabled ports for IMAP and SMTP.

Apple’s Mail Support page has some HOWTO’s for adding new accounts:

• Mac 101: Mail
  
• Mail 2.0 Help: Setting up you email accounts

Here are some screenshots (created with Skitch, brilliant app) of my setup to MS Exchange (Mail->Preferences):

• Account Type: Exchange – Apple Mail currently supports one Exchange account type. I am not sure why since it is only IMAP, but after you create one, you no longer have an option to create a second Exchange account type.
• Description - Some intelligent or clever name for this account, user defined.
• Email Address – Your Exchange email address, this will be used on replyto’s.
• Full Name – Self explanatory.
• Username and Password – Microsoft NT or Active Directory username, can be in the format domain\user.
• Outlook Web Access Server – I am not sure what this is used for, it does not seem to add any functionality. It would be nice if Apple Mail could use RPC over HTTPS.

• Advanced Tab – All defaults, except for the check box for “Use SSL”. This is highly recommended so that your login credentials are not sent in the clear.

• SMTP Server Settings – pop up window displayed by pressing the “Server Settings…” button.
  
• Outgoing Mail Server – Your organization’s SMTP server.
• Use Secure Sockets Layer – Highly recommended to be checked.
• Authentication – NTLM is the default for an MS Exchange SMTP gateway, Mail does support other authentication types. Your organization’s internal mail relay might not be an Exchange server.
• User Name, Password and Domain Name – Your NT or Active Directory login credentials.

Inbox Nil and the Mail Ninja, Intro

I am planning a multi-part series on how I use Apple’s mail.app to parse gobs of e-mail everyday. The sheer volume of e-mail has grown over the years and in many cases the meaningfulness has decreased. Back in April of 2006, I wrote a post entitled Mail.app Rocks! The post has been read heavily and I have received much positive feedback on its content.  Inbox Nil and the Mail Ninja will follow-up on my experiences with mail.app.

Inbox Nil and the Mail Ninja will detail how I am using mail.app with my organizations’s MS Exchange server and the plug-ins I use daily. I will also reveal on how I integrate David Allen’s Getting Things Done methodology and Merlin Mann’s Inbox Zero theory with mail.app and other GTD-ish applications.

Inbox Nil is my application of Merlin Mann’s and David Allen’s wisdom. And the Mail Ninja part, well it sounded cool.

Stay tuned, more to come this week (I am on vacation!)