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
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”:http://www.askdavetaylor.com/how_to_restore_imac_macbook_from_time_capsule_machine_backup.html 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
So “Vyshemirsky”:http://vyshemirsky.blogspot.com/2007/10/how-to-synchronize-ical-with-exchange.html found another solution to this problem called at http://ww.snerdware.com/groupcal and they have another than does the same for contacts to the Address Book. Although “Judi”:http://judismith.wordpress.com/2007/09/13/still-no-ical-exchange-sync/ found it buggy and it deleted appointments in Exchange and iCal (so backup before trying any of this!). And “some”:http://forums.macrumors.com/showthread.php?t=471498 think they are out of business.
There are real issues like “Justin”:http://justinhartman.com/2008/03/31/apple-ical-microsoft-exchange-fix-for-leopard/ point out and “Fragens”:http://thefragens.com/blog/2008/08/ical-exchange-time-zone-fix-chapter-2/ 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!
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 email@example.com or firstname.lastname@example.org, while having a @gmail.com or @me.com 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.
Most of this is pretty easy, email works fine, but doesn’t allow vanity domains, so everyone has to use email@example.com
For Calendar, the answers are complicated as usual, here is one view
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.
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”:http://www.youtube.com/watch?v=S9Jp87lIwU8 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 🙂
Another piece of the puzzle. We are still using an Exchange backend but it sure would be great to have an alternative that hooks into an iPhone 3G and the Mac applications (Mail, iCal, Address Book) without dreaded sync.
Right now we use a hosted Exchange and then Entourage on Mac for Calendars and Contacts and Mac Mail for email. Then iPhone 3G plugs into ActiveSync on Exchange. While we cold substitute Kerio Server for Exchange Server, we are still relying on smaller hosters.
Google has solves parts of this. On Blackberry, iPhone and Mac, you can real time sync Gmail through IMAP. However, for contacts and calendars, things are messier. Blackberry has IMAP of course and there is a Google synchronizer that runs on the Blackberry as well for calendar. For Mac and iPhone, you can do Mail, but no answer for contacts and calendars other than very slow isync that is buggy too.
With “Caldav”:http://www.google.com/support/calendar/bin/answer.py?answer=99358″ you can now get email on Mac Mail and then iCal for calendar. It is complicated as heck, but the key is to setup an iCal account and then there is a magic Account URL of the form https://firstname.lastname@example.org/user where you type in your username just before the @gmail.com
The sync is then every fifteen minutes on a polling basis and is hopefully faster than the amazingly slow calendar sync between Entourage and iCal.
iCal is nice in that it can show many different “Calendars”:http://www.apple.com/downloads/macosx/calendars/ like for instance public holidays in separate colors.
It also allows you to subscribe to someone elses calendar. That is incredibly complicated as well, but “involves”:http://www.google.com/support/calendar/bin/answer.py?answer=99358&topic=&useful=1&expand_useful=1&#helpful signing online to Google Calendar and then in your calendar, there is huge magic number before email@example.com called your Calendar address. You then add another iCal entry with your user name and password and then type in https://firstname.lastname@example.org/user and you can see it.
Now how do your get your calendar up to Google Calendar in the first place? Well, if you have Outlook that isn’t a problem. “Google Calendar Sync”:http://www.google.com/support/calendar/bin/answer.py?hl=en&answer=89955 does this in real time with Outlook by downloading a little program. It lets you 1-way sent Outlook to Google or even do 2 way. We just need one way.
If you don’t have Outlook around talking with Exchange, then you have to take Entourage and sync it once with iCal and then use the iCal to Google Calendar sync. Basically, you take iCal and choose File Export to create a .ICS file which Google Calendar can “obscurely”:http://www.google.com/support/calendar/bin/answer.py?answer=37118&cbid=-q8ybr6bdphj0&src=cb&lev=answer to to the calendar list on the left, click on the Add down arrow and select import calendar.
Finally with “OS X 10.5.3”:http://googlemac.blogspot.com/2008/05/mac-os-x-1053-sync-google-contacts.html you can now sync the Address Book with Google contacts as well which is pretty cool. Just go to the Address Book/Preferences and select Sync with Google.
Now, the only real piece left is what to do with the iPhone, obviously Mail works, but there doesn’t appear to be a real time way to have iPhone sync contacts (you have to go through Mac address book) nor calendar (same deal). But getting closer!
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
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”:http://www.kerio.com/manual/kmsug/en/ch11s05.html#sect-icalcaldavset 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”:http://forums.kerio.com/index.php?t=msg&th=13051&start=0&S=271491edc283c6f0ec2b666277b0b83e should work | wait for v2 | Kerio looks like Exchange so should work with iPhone v2! |