How To Sync Your Calendars, Contacts, Todo’s, Files and Other Data Between Multiple Computers, Your iPhone and iPad

This is my ultimate guide to keeping your calendar, contacts, bookmarks, todo’s, files, passwords and other items synchronized between multiple computers, iPhone and the iPad. Warning, this one of the most geeky posts I have made yet! But if you are a productivity freak like me, this will help you a lot!

So, I work with a desktop, laptop, iPhone and iPad. My biggest pet peeve was having my contacts, calendar, documents and other items missing from my computer or device when I needed it!

So began my quest to find a way to manage all these data sets that I use on a daily basis. A lot of solutions came at a monthly cost. That was a no-no for me and so I started experimenting with all the different free services out there including some freemium services.

After much trial and error, I believe that I have found the optimum solution for now. So here’s how I do it:

sync calendar, contacts, todo, multiple= Contacts & Calendars

Syncing contacts between my Desktop and my iPhone and iPad is simple enough. I just use iTunes and choose to sync my contacts and calendar. So every time I dock my devices to my main computer, the calendar and contacts are synchronized.
But synching between my desktop and laptop proved to be a real pain. That is until I found Plaxo’s sync point service.

Sign-up with Plaxo for free and download their desktop app to do your first sync.

Next, select “add a synch point” and choose to add a new computer. You can also sync with Google apps (Google Calendar and Google Contacts) but I found it was not necessary.

Now download the Plaxo desktop application on your laptop and sync with the same Plaxo account. Voila! Now your Address Book and iCal will always be in sync!

Now you are free to add contacts or appointments from any device and at the end of the day they will all be on all your devices.


Next came the todo list. Now if you are happy using the todo’s inside iCal, then you can ignore this part.
But being the productivity geek that I am – I needed something much more powerful. The Rolls Royce of task management apps that I found is called “Things” from Cultured Code.

And the reason they rock is because they have a desktop version, iPhone version and iPad version. Now you will need to pay for all 3 versions. This is fine for me because its a one-time expense but I use it everyday!

So once installed, all devices sync automatically with each other every time these devices are on the same WiFi network. No need to dock.

Also, by placing the Things database file on my Dropbox folder (read below), my todos also sync with my laptop the same way.

Additionally, I created a special calendar in iCal to sync with my ToDo items, so that any item I specify in Things that has a date, the item and task will be added to my iCal.

Now I can manage my todos from any device and they will always be synchronized.


Apple Mail-1With email, this is also easily managed by Apple’s Mail application in all devices.

However, the key is to set up IMAP accounts for your mail accounts. This way, if I read any email from any device, it is marked as “read” on all my devices.

So again, I can check email or send email from any device and a the end of the day, all the mail accounts are synchronized.


Drop Box LogoDocument is a rather tricky one. To sync documents between computers, the best solution out there is DropBox.

Go to DropBox and create a free account. This allows you 2GB of data to sync. I found this to be more than enough for my needs.

Now you install the Dropbox desktop app and create a folder that is always synchronized. Now install Dropbox in your laptop and you will have the same folder on both computers that is always synchronized.

Next, install the free Dropbox app for iPhone and iPad. Now all the files in your Dropbox folder will appear here too.

Now with iPhone and iPad, they way to view and edit docs like MS Word, Excel and Powerpoint and PDFs are managed by another app I use called “Docs2Go”.

This is a paid app but I have found that it is very useful if I ever need to create or read docs on my mobile devices.

Docs2GoDocs2Go also come with a desktop application that allows WiFi synching with the iPhone and iPad versions. But in order to sync – you need to launch the Docs2Go desktop all and click the synch button. That’s too many steps for my liking!

Now comes my solution – because I have Dropbox installed, I just added all the document folders I manage with Docs2Go inside the Dropbox folder. So now, I can access these documents inside my mobile devices via Dropbox without needing to manually sycn my Docs2Go folder.

As a side note, the Docs2Go apps also allows you to sync with your Google Docs account anywhere you are. These are additional option which I don’t really use right now but may be useful for you if you collaborate with others and want to share files using Google Docs.

Having said that, Dropbox also allows you to share selected folders for collaboration. So its your choice how you want to make the most of these features.

Text and Multimedia Notes

Evernote LogoFor text and multimedia notes like photos and audio notes, the simplest way is to use Evernote.

Like Dropbox, they have a desktop app, iPhone app and iPad app. This app allows you to take photos, record an audio note or just type some text.

All these will be automatically synchronized between all your devices.

Like Dropbox, there’s a limit to how much data you can transfer each month. Again, I have found that the free account has more than sufficient data space for my needs.

Passwords and Bookmarks

Google Chrome-4Finally, I should mention about passwords and bookmarks. This is still a work in progress for me because I have not found the perfect solution yet. But what I got going right now is working ok.

My default web browser is Google Chrome. Google Chrome automatically allows you to sync bookmarks with your Google Account.

So on both my computers, the browsing experience is identical. e.g. I have the same book marks and theme.

As for passwords, I use a software called 1Password. They also have an iPhone and iPad app. So far, this app keeps my passwords and secured notes synchronized between my main computer and my mobile devices.

The only limitation right now is that the Google Chrome iPassword extension is still in beta mode and does not have the full features yet.

But like I said, this is an acceptable solution for now.

Recommendations and Future Updates

This quest of mine to find the ultimate mix of software, apps and best-practices to manage all the common data between my computers and devices is ongoing.

If you have any recommendations please do add them to the comments below.

If you want to keep in the loop of my discoveries and experiments, please subscribe to this blog.

If you enjoyed this post, please also subscribe to my RSS feed! You can also follow me on Twitter here.

14 thoughts on “How To Sync Your Calendars, Contacts, Todo’s, Files and Other Data Between Multiple Computers, Your iPhone and iPad

  1. soonwei

    Thanks for this Brian, it’s helpful!

    Just trying to figure out optimum productivity esp when I’m using a PC desktop and blackberry (mainly for work) and an Ipad. Any suitable mix for that?

    Hope all is well :)

  2. BGC


    Thanks for the post. It seems to be predicated on use of apple devices only. I would love to be able to sync emails and calendar between a desktop pc, laptop pc and iPhone. I use Thunderbird right now, but have the full Office 2010 suite if i want to use it. I’d also like to be able to sync word docs between laptop and desktop.

    Just starting my search for a solution, but liked the style of your blog post and thought I’d comment.


  3. Brian Wong Post author

    Yes, this post is a sharing of my situation which involves mostly Apple products and software. There are too many other possible variations to cover otherwise. Thanks for dropping by and I hope you find the solution for your set up.

  4. Tim


    I think your post is excellent and very helpful thanks. I have had the same objective as you for many years. When did you post this? I suspect it predates iCloud, which simplifies syncing of contacts and photos for most of my devices.

    iCloud doesn’t sync folders, so like you I use Dropbox, which works brilliantly between my two PCs (one Win7, one XP), my MacBook Pro and my iPad. I also use CloudOn on the iPad which is free in place of Docs2Go.

    Using an imap email account keeps all emails synced. What I haven’t yet resolved is syncing contacts to my XP machine as iCloud doesn’t work on XP. Do you know if Plaxo will be able to work with iCloud?



    I love that image, it’s a proper flow chart explaining the process. I did use Google chrome to store bookmarks for a while, but switched to xmarks in the end. It’s a really good extension.

  6. David

    Very nice to share your org. techniques. However, there are some pretty bad reviews of Things at the app store. Hmmm…

  7. Brian Wong Post author

    Thanks. Well, I like Things because its simple and it works on my iPhone, iPad, Laptop and Desktop. Been using it for a long time now and I have no problems with it considering it needs to sync across so many devices.

  8. Ethan

    Several weeks ago my wife decided to update our desktop computer’s Google Chrome. (She is the “systems administrator” for this computer.) Several hours later after she had done the updates & was off the computer I went on the updated Google Chrome only to find ALL OF MY GOOGLE CHROME BOOKMARKS GONE. In lieu there was totally different & old bookmarks from an older NON-CHROME version of Google. Despite having an external WD terabyte backup drive – well NONE of the Google Chrome were found there.Now here is the real kicker…a few days ago my wife turned on her “The New iPad”. A new screen icon that read “Destop Bookmarks” appeared. When she logged on to Google Chrome all the missing bookmarks were there. We went on both our desktop and laptop (wi-fi) logged onto Google Chrome nothing. Do you know how to copy – transfer from “The New iPad” those “Desktop Bookmarks (Google Chrome Bookmarks) to our regular desktop computer. I just can’t envision having to open copy, paste & send @ 700 URLs’ ,then open and bookmark each one. Any advice would be greatly appreciated. Thank you for your time.

  9. paai

    Nice, but worthless for people like me, who live in an environment that also has Microsoft, Linux and Android.

    My solutions are as follows:

    For email, any IMAP account will do, as long as you use the local storage with care. But actually, I always read mail on a single machine using NX (see below).

    Calendar and addresses: my google account syncs them over the Linux, Microsoft and Android platforms. Presumably on the Mac too, dunno.

    Passwords: the program ‘pwsafe’ is available for Linux, Microsoft, the Mac and Android (even Maemo on the N900).

    All other files, including the password data are synced with rsync.

    Of course I can open virtual folders on other machines with nsf, or better ssh.

    As I am one of the happy people that can use Linux on their job, most real work is done in a so-called NX session, which is like a virtual desktop on steroids. It has clients for Microsoft and Linux, but the server must be a Linux machine. So personally I have everything covered.

    Alas! My wife bought a Mac and an Ipad, and the conflict of cultures between the very, very open Linux and the very, very closed world of the Ipad as yet is an insurmountable obstacle. Any suggestions are welcome.


  10. Munro Murdock

    I know this is an older post, but great tips nonetheless. The Things app is even better now with Cloud sync. Any plans to move from DropBox to Google Sync? Any other updates to your process since posting the article?

  11. Melissa S.

    This is just what I needed to figure out how to sync my iPad, iPhone and PC calendars… though I mostly use Calendars on my Apple devices only. Also, gave me info I needed to troubleshoot email sync… without IMAP right now I’m stuck with my email being all over the place, but I feel better knowing why it’s that way. Thanks!

  12. Mike McMenamin

    Brian I cant tell u what a relief to see someone facing the same problems.. I use doc to go.i also tried part of your idea but i wasnt sure dropbox could hold all thedata 4 free.
    I need a task management system that doesnt interfere with actual appointments.
    I am not sure how to get ical to sync with laptop. I would rather type most of my tasks/ todos on the keyboard of laptop..mike
    So is it better to use icloud and how would i do it then?
    Do u still recommend ical?

  13. Jerry Terstiege

    Hello Brian:

    This post and the comments following are all from early 2012.

    Is this all still current, or would you revise it based upon changes to Apple, Plaxo, etc.?

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