blog home about our NYC Mac support site

IMAP, Exchange, ActiveSync, CalDAV, CardDAV: Why are email protocols so confusing?

Image by Jonny Hughes, courtesy Flickr Creative Commons.

Image by Jonny Hughes, courtesy Flickr Creative Commons.

I was reading this thread on Apple’s discussion forums and realize that figuring out what can synchronize to what when it comes to mail, calendar, and contacts can be pretty headspinning.

Here’s the thing: there are multiple protocols for synchronizing mail, calendar and contacts, variously supported by different servers and client software. I’ll try to explain.


The Summary:

Mail will always synchronize with whatever software or device you’re using.

However, for calendar and contact sync:

Google, iCloud, Yahoo, AOL, OS X Server calendar and contacts:

  • Will sync with mobile devices
  • Will sync with Mac computers
  • Will sync with some Windows computers, depending on version and software being used

Exchange Server, including Office 365, calendar and contacts:

  • Will sync with mobile devices
  • Will sync with Mac computers
  • Will sync with Windows computers (Hotmail) calendar and contacts:

  • Will sync with mobile devices
  • Will NOT sync with Mac computers
  • Will sync with Windows computers


The Ugly Detail:

Open protocols:

  • IMAP: Syncs mail. Supported by countless software and provided by almost every kind of mail server, including Exchange, OS X Server, iCloud, Google, Yahoo, AOL, etc.
  • CalDAV: Syncs calendar. Developed by Apple. Supported by modern mobile platforms, and some desktop software, including Mac iCal/Calendar since Leopard. Provided by iCloud, OS X Server, Google, Yahoo, AOL, and some other servers (but not Exchange or
  • CardDAV: Syncs contacts. Developed by Apple. Supported by more recent versions of modern mobile platforms, and some desktop software, including Mac Address Book/Contacts since Snow Leopard. Provided by iCloud, OS X Server, Google, Yahoo, AOL, and some other servers (but not Exchange or
  • POP: Downloads mail to inbox, but that’s all. No synchronization, no folder awareness. Not recommended for modern living unless you exclusively use one well backed up computer, and no devices. Provided by almost every kind of mail server, including Exchange, OS X Server, Google, Yahoo, AOL, etc., and occasionally POP is the only option available (e.g. the freebie mail you get with a GoDaddy domain, some ISP’s, and some older web hosts).

Microsoft protocols:

  • Exchange ActiveSync (EAS): Syncs mail/calendar/contacts/tasks/notes. Almost exclusively supported only by mobile device clients. The only desktop clients on any platform that supports EAS are Outlook 2013 for Windows and Windows 8 Mail/People/Calendar (and Outlook 2013 will only allow connecting to non-Exchange EAS services such as and paid Google Apps). Provided by Exchange 2003 and later, Office 365, (Hotmail), paid Google Apps, and some other servers.
  • (Since EAS was designed to be lightweight, it is more limited in its capabilities and how much data it communicates than other protocols; this may be why it is not widely used by desktop software, and  I suspect but have no evidence that Microsoft may have restricted EAS use in desktop software through licensing restrictions.)
  • Exchange Web Services (EWS): Syncs mail/calendar/contacts/tasks/notes. Not supported by any mobile device clients. Desktop clients I’m aware of that support EWS include Outlook for Mac 2014, Outlook for Mac 2011, Entourage 2008 Web Services Edition (aka version 13), and Apple Mail/Calendar/Contacts/Notes (since Snow Leopard; Notes since Mavericks, I think). Outlook for Windows does not use EWS. Provided by Exchange Server 2007 and later, and Office 365.
  • MAPI: Syncs mail/calendar/contacts/tasks/notes, plus all other information available from an Exchange server. It is the “native” connection protocol for Exchange since 1997 despite Microsoft’s attempts to get away from it. Only supported by Outlook for Windows (all versions), though Outlook 2001 for Mac OS 9 also supported it. Provided by all versions of Exchange Server, Office 365, (Hotmail), and paid Google Apps.
  • WebDAV: Syncs mail/calendar/contacts, slowly and badly. Now deprecated. Not supported by any mobile device clients. The only desktop clients on any platform that support it are Entourage 2004 (aka version 11) and 2008 (aka version 12). Provided by Exchange Server 2003 and 2007.

API access to contacts:

  • API for Gmail, FaceBook LinkedIn, Yahoo: Syncs contacts. These services have an internal proprietary method for accessing their contact information. OS X Leopard through Mountain Lion can utilize it to synchronize contacts with Google and Yahoo. On Mountain Lion through Yosemite, you can use CardDAV instead, as well as synchronize with FaceBook and LinkedIn using their own internal methods.


 Related Posts

Top 5 Apple Mail Plugins

Set Up Your Email to Send an SMS Text Message to Your Mobile Phone

iPhone Keyboard of the Future?


A new portable keyboard, to be used with the iPhone, iPad, or any other Bluetooth-enabled device, has just been announced. It has a totally new design from anything we’ve seen before. It’s called the TextBlade.

It’s made of 3 pieces, which fold together into a case (and the case doubles as an iPhone stand). Folded down, it’s less than half the size of an iPhone — 4 inches long by 1 inch wide.

The way they get it so small: There are only 8 keys (4 for each hand), and each key can type multiple letters depending on the direction you push the key. They claim that it feels like a standard-size keyboard.

The company has raised $1 million in advance purchases. They’re also donating 10,000 TextBlades to elementary schools.

The price: $99. Or you can get 6 for the price of 5.

Availability: Mid-March, as of right now anyway.

I’ve been waiting years for a truly portable keyboard that feels like the real thing. Glad to see that inventors are still working on a solution.

Related Posts

Best iPad Stylus?

Tile and iPhone, to Track Your Belongings

Best of CES Roundups


The Consumer Electronics Show just finished up in Las Vegas — that’s where all the ideas for new technology tend to be shown off for the first time.

Here is a roundup of cool stuff from CES, from different publications.

Engadget includes among their coolest items:

  • Wireless headphones by a company called “Bragi’s The Dash”
  • 3D printing with stone, wood, iron, and other composites through MakerBot

Mashable talks about “what we learned” at CES and what’s going to be big, including:

  • Fashion & tech
  • Drones
  • Selfie stick
  • Smart homes

Molly Wood at the New York Times talks trends, although she thinks most of these won’t be ready for consumption for at least 5 years:

  • Driverless cars
  • 3D-printed food
  • “Roboticized homes”

Lifehacker has an article on stuff from CES that you might actually want & use, including:

  • Sling, to watch ESPN over the internet
  • Faster computer processors are coming from Intel
  • Smart devices for home automation
  • 4K Blu-Ray players

Which of these will we actually be buying within a few years? We’ll need to wait and see…

Related Posts

Last year’s Best of CES Roundup

Top 5 Cool Hardware Finds from Macworld

Tile and iPhone, to Track Your Belongings


A friend of ours sent us Tiles as a gift for the holidays. Here’s what it is, and how we’re using it.

Tile is a little piece of plastic, about 1-1/2” square, with technology inside. And there’s an iPhone app to go with it (there’s an Android app too).

You link the white plastic tile to the app with a secret button, over Bluetooth. Once they are linked, you can pinpoint the last known location of the tile (and whatever it’s attached to, of course).

Attach it on your keyring. If you lose your keys in the house, open up the iPhone app, and instruct the Tile to make some noise so you can find it again!

Or if you’re not sure if you left your keys somewhere, you can use the iPhone app to see the last place your Tile checked in.

Other ideas of where to attach it:

  • Put one in your wallet.
  • Put it into your backpack or handbag.
  • Attach it to your fancy camera.
  • The website even shows one stuck to a remote control, so if the remote gets lost in the cushions you can find it again.

My observations:

  1. I find the Tile to be a bit bigger than I hoped. It’s pretty substantial in a wallet or on a keyring.
  2. It provides a sense of security, even though I don’t lose things that often.
  3. I can see it being very useful for finding my keys when I’ve left them in a pocket somewhere in my home. The “make some noise” feature (they label it “Find”) is fantastic.
  4. I’m concerned about the potential for tracking somebody else. This is possible if 2 people are using the same Tile account—therefore you must choose a good password, so nobody can log into your Tile.

Cost: $25 per Tile; price comes down substantially if you buy a few at once (up to a 40% discount, if you buy 12 Tiles). The app is free.

Related Posts

Don’t lose that Mac MagSafe 2 converter!

5 Top Mac, iPhone, and iPad Accessories for New Yorkers on the Go

The most beautiful app I’ve ever seen is a game

We don’t usually recommend iOS games here at IvanExpert, but we wanted to make an exception for Monument Valley. It’s beautiful, both visually and aurally. It’s mildly challenging, but by no means  impossible, and there’s no time pressure, no score, no way to die, and no way to get stuck. It just waits for you. It’s strangely relaxing to play. It’s no accident it was an Apple Design Award winner.

Monument Valley is a puzzle game in which you move a figure named Ida, a character in a deliberately vague storyline, through a series of three-dimensional “monuments” that resemble a cross between M.C. Escher and Dr. Seuss in their oddball geometry. In fact, what makes the game fascinating is that you have to do things that are only possible as a result of your 2-D perspective on the 3-D environment. It’s hard to explain; you should just try it out. For $3.99, it’s well worth it for such an enjoyable labor of love.

If you solve all the levels, there’s a $1.99 in-app purchase to acquire eight newly released ones. If you have an iPad, I suggest you play on that, to get the full impact of seeing the game on the larger screen.


Highly recommended!

Related Posts

Customize Notification Center in iOS 8

Use the Stand Up! iPhone App to Take Regular Breaks


Simple, Inexpensive Home Camera Monitoring with your iPhone

Are you interested in setting up a simple camera monitoring system at home (or at a small office)? Here are a few options.



Nest, the company that brought you the “smart” thermostat (and is now owned by Google), has a new product that we’re interested to learn more about. It’s called Dropcam.

Dropcam is a video camera that can be used for home security and baby monitoring (and business security too, if you have a small business). Cost is $200 for one camera.

It’s supposed to be super simple to set up, and works on your wifi network. Plug it into your USB port on your computer for initial setup; then disconnect and put it wherever you want to start recording.

You can watch the video from your iPhone or Android phone using their app. Camera can be set up to turn on or off at specific times, or it can be motion-sensitive. It can even push alerts to you if it senses movement. The camera is also infrared, so it can “see” in the dark.

There’s also a separate charge if you want Dropcam to store your videos on its website for a week ($99/year) or a month ($299/year). So you can go back and review the footage if something has happened.



Another option is Vuezone, from Netgear. It’s a small wifi camera with infrared that you can set up anywhere in your home. It has iPhone and Android apps so you can see what’s being recorded. With this system you also need to purchase a base station. For 1 camera and base station the cost is $130; for 2 cameras plus base station it’s $200 (so you get twice as many cameras as the Dropcam for the price).

If you want to get alerts and have Vuezone save your video for later viewing, the cost is $50/year for up to 5 cameras and 250MB of storage, or $100/year for up to 15 cameras and 500MB of storage.



A third option is Belkin’s NetCam. Like the others, it connects to your wifi network, and you can watch video from your mobile phone (or computer). Also like the others, it’s got an infrared camera.

The camera, which is HD wide-angle, costs $130.

You can set up an account to have video saved whenever the camera detects motion, for later viewing (up to 30 days). Right now the cloud video saving service is free; after the initial testing “beta” phase there will be a monthly fee (prices to be announced).

Related Posts

How to Use the Web Securely when Away from Office or Home: VPN

Are your email passwords secure?

Send Email Later from Your Mac

Have you ever wanted to schedule an email, to be sent at a later date? Perhaps you want to make it look like you’re not at your desk. Or maybe you want the recipient to think you waited awhile to answer an email. Or you don’t want everyone to know that you’re up at 3 am answering emails.

Here are solutions for sending email later from your Mac.


If you use Apple Mail: SendLater

Cost: 9 Euros (just over $11)

This piece of software is installed on your computer and lets you schedule your emails in Apple Mail. Remember that for it to work, your Mac has to be on and Apple Mail must be running at the time you’ve scheduled the send.


If you use Apple Mail: Mail Act-On

Cost: Free 30-day trial; $30

This software does much, much more than just let you schedule emails for later. You can create powerful rules for inbox and sent mail; create templates for email replies; and set a ton of other workflow options. Again, for the send later function to work, your Mac must be on and Apple Mail must be running.


If you use Gmail or Google Apps: Boomerang’s Send Later

Cost: Free 30-day trial; $5/month for Gmail unlimited emails; $15/month for Google Apps unlimited emails

This service connects to your Google account and lets you schedule emails from within Gmail or Google Apps. (If you don’t know if you have Gmail or Google Apps: Is your email Then you have Gmail. Is your email but you check it on Google? Then you have Google Apps.)

This only works if you write your mail inside a web browser, not if you use Apple Mail for reading and writing your Gmail/Google Apps email. It works with Chrome, Firefox, and Safari.


If you use Gmail or Google Apps: Right Inbox

Cost: Free for 10 emails/month. $60/year for unlimited emails and reminders, for both Gmail and Google Apps.

This is a service you use with Gmail or Google Apps. Note that the price is better than Boomerang if you use Google Apps. Again, this solution only works if you are writing email in a web browser. Works with Chrome, Firefox, and Safari. You can also use it to set up recurring emails, email reminders.


If you use Outlook for Mac: Nope. At this time there’s no way to schedule emails to be sent later (It’s a feature in Outlook for Windows only.)

iPhone and iPad: Nope. This feature doesn’t exist for iOS — yet.


Related Posts

Top 5 Apple Mail Plugins

Set Up Your email to Send an SMS Text Message to Your Mobile Phone

5 Tools and Apps from the MacTech Conference

Caroline with R2D2 at MacTech.

Caroline with R2D2 at MacTech.

We just got back from the MacTech Conference in Manhattan Beach (Los Angeles), where we learned a ton about everything related to Mac consulting and support.

A lot of it was pretty technical. But these 5 cool tools and apps are useful for almost any business, so check them out!

1. ODesk
Find freelancers across the country and around the world for a variety of needs. They’re all rated and categorized by specialty. The website takes a 10% cut.

For $25/month you can watch as many video tutorials as you want, on topics as diverse as iPhone app programming, to photography, to management, to editing videos, to using Excel…

3.  Trello
This web-based project management system is particularly great for creating checklists that everyone in your group can access. And its calendar syncs to your Apple calendar. Use it on your Mac, iPhone, iPad, Android. The basic version is free.

4. Shapes
This $10 piece of software lets you create easy diagrams, charts, and workflows.

5. Pop
The name for this iPhone app stands for “prototyping on paper” and if you are thinking of designing an iPhone app, you should definitely try it out. You draw your app design and then make your drawing functional. Essentially it lets you create and test your app idea before you need to start the hard work of hiring people to make it for you. And it’s free for 1-2 projects! ($10/mo for 2-10 projects.)

Related Posts

MacTech Boot Camp: Back Up Your Mac

Top 5 Mac Tips and Tricks from Macworld

Customize Notification Center in iOS 8

This is what my Notification Center looks like today. Including a nice NYC photo from Yahoo Weather.

This is what my Notification Center looks like today. Check out that nice NYC photo from the Yahoo Weather app.

We finally advise that it’s safe to upgrade your iPhone or iPad to iOS 8. The number of problems after the upgrade has quieted down after Apple’s updates.

I just upgraded my iPhone to iOS 8 and am taking advantage of the Notification Center.

What is the Notification Center? Put your finger at the very top center of the screen, and swipe down. You’ll get a page of useful info having to do with your day. (Note that at the top you have a Today button and a Notifications button.)

You can edit what shows up in the notification center. To edit: Scroll down to the bottom of the Notification Center page and click the Edit button. You have options to add or remove, such as calendar, reminders, and stocks. You can also change the order by dragging.

Did you know some non-Apple apps have “widgets” to allow you to show relevant into in your Notification Center as well? Here are a few. (You need to download the app first, and then go into Notification Center > Edit and click the plus sign to get them to appear.)

Some of the best apps with a Notification Center option:

Evernote: Add a note right from here

Wunderlist and Clear: Shows your items on your to-do list

Weather Channel and Yahoo Weather

OpenTable: Shows your dinner reservations

Dropbox: Shows the most recent file changes

New York Times and Breaking News: News highlights

ESPN SportsCenter: Quick access to scores

Related Posts

iOS 8 Review Roundup

Do a quick check to make sure your iPhone is backing up


Best iPad Stylus?

The Pogo stylus.

The Pogo stylus.

I read the technology reviews site The Wirecutter, which tests tech hardware and software and advises on what’s the best and why. (I highly recommend you subscribe to their weekly email newsletter; they also have a related site The Sweethome for household items.)

Last week they published an article on “The Best iPad Stylus for Note-Taking” — their pick is the Pogo Stylus, for $20.

So I purchased one at B&H Photo and am testing it out.

My best choice for a stylus up until now has been the Adonit Jot pen, which starts at $20. I like the Adonit Jot because the little plastic disk on the nib makes it easier to do precision writing and drawing, on the exact spot you want. However that little plastic piece is easy to lose (as is the cap), plus it doesn’t feel completely natural to use a pen with a plastic disk on the end.

The Pogo is inexpensive, yet it feels sturdy and easy to hold–and no pieces to lose. The rubber tip doesn’t let you get quite as thin and precise a line as the Jot but it does do almost as well for note-taking. This is something I could throw in my bag without fear of destroying it, and it feels much more natural to write with. Plus it’s also great for tapping buttons and navigating around. So I’d say for ease of use, it wins over the Adonit Jot.

My 2 favorite note-taking apps:

  • Notability, $3: Best for basic note-taking plus has a microphone feature to do an audio recording of a meeting or lecture as well.
  • 7NotesHDPremium, $8: Its main advantage is that it converts handwriting to text, either as you type or after the fact. (Only the premium version does this.) And it does it very well; it didn’t make one mistake with my handwriting. Pretty amazing.

My conclusion is that unfortunately it’s still much faster to take notes with a pen and paper than it is with a stylus on the iPad…and speed is what’s most important, when I’m in a meeting and don’t want to miss anything. I’m going to try the Pogo and iPad combo at an upcoming event, to get some real-world experience.

Related Posts

10 iPad Apps for Work, from Macworld

Scan from Your iPhone or iPad

About IvanExpert

IvanExpert provides superior Mac, iPhone, and iPad support for small businesses and home users in New York City. We provide on-site help with a range of Apple computer and mobile issues.

Sign up to get our blog posts by email

Sign up for our monthly email newsletter