Mac Mail has stuck messages in Outbox

Apple – Support – Discussions – Mail stuck in OUTBOX …

The problem is a corrupt Outbox. I read about this on
the ATT trouble shooting site. Delete the Outbox and
mail will create a new one. This solved my problem with
email sitting the Outbox forever and never being sent.
To be safe, I dragged my Outbox to a different location,
then started mail. Problem solved!

The Outbox is found: Users/YourName/Library/Mail/Mailboxes/Outbox.mbox

MacBook Air reinstallation and hopefully Time Capsule transfer

OK, so I’ve completely wiped my MacBook Air, time to rebuild it. Here is a list of things that have to happen. Sure sounds Windows like doesn’t it 🙂

# Remote install Mac OS X. Sigh. This is going to take 4 hours over the air apparently
# Try the “Time Capsule recovery”: which comes during the standard installation, it asks if you want to restore from Time Capsule
# Run Settings/Software Update to get me to 10.5.5.
# Install Microsoft Office 2004
# Install PDFPen
# Install Quickeys (or a good time to get F2 and F4 working with other stuff)
# Copy over my Music
# Make Mac Mail work with my email accounts
# Make Entourage work with our Exchange server

iCal to Exchange before Snow Leopard

So “Vyshemirsky”: found another solution to this problem called at and they have another than does the same for contacts to the Address Book. Although “Judi”: found it buggy and it deleted appointments in Exchange and iCal (so backup before trying any of this!). And “some”: think they are out of business.

There are real issues like “Justin”: point out and “Fragens”: has a fix for. Outlook 2003 and earlier uses non-standard time formats like _(GMT+02.00) Harare/Pretoria_ whereas Apple uses _Africa/Johannesburg_ and so when iCal gets a calendar request from Exchange, it simply adds two hours to the event start time becaue it can’t deal with GMT+2. He wrote a script you run on your computer that runs in Mac Mail, it intercepts the message and then fixes the dates. Clever guy!

Backend comparisons: Exchange, Google, or MobileMe

Whether you are a small business or a family, everyone needs the same three things:

* Email ideally from your own vanity domain, whether it is or, while having a or is nice, we all want our own identity. And we need lots of disk space, at least 2GB per user. Have wireless sync on iPhone or to Mac Mail.
* Calendar. I need to see someone else’s appointment and also have a shared calendar for common appointments. See them in colors on the iPhone or Mac iCal
* Contacts. Have contacts that are the same between your iPhone and your Mac Address Book.

h2. MobileMe

Most of this is pretty easy, email works fine, but doesn’t allow vanity domains, so everyone has to use

For Calendar, the answers are complicated as usual, here is one view

Calendar Sharing using .Mac/MobileMe – AppleInsider

Here’s the setup:

Mom: has shared calendars S1 and S2
Dad: has private calendars A1 and A2, and shared calendars S1 and S2
Kid: has private calendars B1 and B2, and shared calendars S1 and S2

As it currently stands, Dad & Kid can subscribe to a published calendar from Mom, but can’t alter it. You have to log in as Mom to change S1 and S2, and then Dad & Kid will get the changes.

But… if you’re on an iPhone, you are one of Mom or Dad or Kid, period. You can’t switch user profiles or accounts, period.

Mom’s phone cannot have any private calendars or contacts. Dad & Kid can’t change the calendars and contacts they share. Bogus.

The reason for this is that the syncing isn’t live on MobileMe – if Dad makes changes, and Kid makes conflicting changes, and alterations hit the server at different times, who wins? (ie, Dad moves an appt in their view from Mon to Tue. The change is only local until they resync with .mac. Before they do, Kid moves *the same appt* from Mon to Wed. They sync first. Now, when Dad tries to sync, the server can’t find the appt on Monday to move, because Kid moved it already. Oops. Confusion reigns.) Push sync alleviates this, since changes are live.

If Dad & Kid can subscribe to a *live* version of S1 and S2 though, using the live push, then syncing is automatic, and more or less instantaneous (there are still boundary cases, of course, which I’m sure someone will toss up as proof of why this could never work… those can be worked around), and you get true shared information.

The current Publish/Subscribe model won’t work for iPhones if the users want to be able to change the shared data as well as view it.

So how does each one of these do?


Hosted Exchange. Well, this isn’t too bad, you can share contact and calendars with iPhone thanks to the ActiveSync. It mainly flunks on connecting to the native Mac Mail, Address Book and iCal. You have to use Entourage

However, Snow Leopard, the next release of Mac OS X will have ActiveSync on the Mac. That means, Exchange ironically is probably the best choice to host mail.

A less higher run alternative is Kerio. This emulates ActiveSync so in essence, could also be a replacement. Net, net, ActiveSync looks like a defacto standard that Mac and iPhone will talk with natively. That is great news. And probably the most likely alternative.

h3. Google

Well, this theoretically should be the best choice. Gmail is the nicest email on the web interface. However, each of the development groups for mail, contacts and calendar is completely different, so today there is no way to sync with iPhone and Mac and also allow shared calendars. Here is the exact state:

* Mail. This is fine, Google supports imap for free with all gmail account and with Google Apps, you can have a vanity domain name work with gmail interface.
* Calendar. Things get worse here. While there is a google sync for the blackberry, there is no sync tool for the iPhone and google doesn’t support activesync. I have tried a third party Nuevasync, but like most third party things, it doesn’t work well. For sharing of calendars, Google has the richest set of multiple calendars and it works superbly on the web, but when syncing with iCal, it uses Webdav, which is pretty buggy causing iCal to crash quite a bit. But it does allow sharing both read-only and read-write.
* Contacts. The reason none of this works. Google contacts don’t have notion of first name or last name, it is one name field, so iPhone’s get confused for sure. They have a Google to Address Book sync, but this manual and uses the really buggy native iSync on the Mac. You want to avoid that at all costs.

Net, net, my money is on waiting for Snow Leopard and then going to a hosted Exchange.


“Appigo ToDo”: was recommended by John. He is right. It is a terrific To Do list manager and it syncs up into the cloud. I’ve normally used Outlook’s Notes to do this between PC and Blackberry (for free!), but iPhone doesn’t support notes nor does Mac Mail and so there is no sync into the cloud.

In any case, this is another example of a smaller dedicated application being better. In truth, I think dividing Calendar, Address Book, Mail and Notes makes more sense than having one monolithic application particularly on devices like iPhone and on today’s fast computers.

Now if only someone made a group scheduling application that worked seamlessly across Mac, iPhone and Blackberry, I’d be happy! And please don’t suggest Exchange with Entourage, it doesn’t do so many important things. Here’s a list:

# iPhone to Exchange. Doesn’t let you add invites from the iPhone. Doesn’t let you schedule recurring meetings that happen say on Monday, Tuesday and Thursday every week.
# Mac Entourage to Exchange. Doesn’t let an assistant see invites coming over email so invites just stack up in someone’s folders. Fix looks like some sort of server rule forwarding which should be form based.
# iCal to Exchange. Well, this one doesn’t work at all without a third party server side piece or very slow client side synchronization using iSync that is very buggy.
# Blackberry to Exchange. This does work fine. Although there seem to be bugs.
# PC to Exchange. Outlook does work well.

The alternative is to go to Google Calendar, and these are the issues:

# iPhone to gCal. No such client that I can find. Google Calendar doesn’t support ActiveSync which is the way that iPhone talk to the world.
# iCal to gCal. No way that I can find that this works natively. That is it synchronizes properly
# Entourage to gCal. Same deal
# Outlook to gCal. This does work but only via an Outlook add-in
# Blackberry to gCal. They have an automatic synchronizer that works.

So gCal works in the Blackberry/PC world, but not in the Mac/iPhone world. Steve had better tell Eric next time there is an Apple board meeting 🙂

Kerio vs. Exchange for Entourage, Mac OS X, iPhone and Blackberry

Well we’ve narrowed down choices to two choices, two hosters against one of three desktop and two mobile clients. Here are the parameters:

Support for either of, in order:

* Mac OS X application. That is Mail, iCal and Address Book that are native to OS X and which is fast.
* Entourage 2004 or 2008 from Microsoft and typically free with any hoster. 2004 is slow as it is a non-native application while 2008 is new and definitely has sync issues.
* Outlook 2007 from Windows or via Parallels on the Mac. But Parallels on the Mac is very slow.

And to support both of:

* iPhone. We really mean the version 2 that will have ActiveSync
* Blackberry. Because folks have these but like the iPhone

So our choices technically are:

* Kerio. This is a Mac messaging, contact and calendaring backend
* Exchange

Here is how the matrix looks right now:

| | Kerio | Exchange | Comment |
| Mac Mail | Runs in Imap | Runs as imap | Both of these work fine |
| Address Book | Needs Kerio Sync to change contacts | Requires Entourage | |
| iCal | Use “Caldev”: on Leopard to allow delegation | Requires Entourage | |
| Entourage 2004 | Via OWA Emulation | Works | Not a native Intel app |
| Entourage 2008 | Need to Test | Need to test | Allows OOF setting |
| Outlook | Need to Test | Unacceptably Slow | |
| Windows | Need to Test | Works great | Assumes Outlook 2008 |
| Blackberry | Need to test | Works great | |
| iPhone | “v2”: should work | wait for v2 | Kerio looks like Exchange so should work with iPhone v2! |