Syncing your Home Folders with ChronoSync

First thing’s first, backup twice. Then check them thrice.

There’s a number of options for syncing your home folders on the Mac, none of them are straight forward, and each offer up a different subset of challenges, but if you can wrap your head around the complexity, they can certainly help you get your computers synchronized. I’ve struggled over the years with getting my files sync’d, and I’m holding out hope that a company like Dropbox will soon let us run an application over our LANs so that we can get a lot of this stuff done at a much quicker pace.

Syncing your files has a host of benefits, of which getting your documents to be up to date on every machine in your house is probably the most lucrative. There’s other reasons, such as syncing movies and music and getting applications synced, but for me, getting my files when I want them, where I want them, is my main objective.

I’ve put together two options to help you guys get this done. Before you get started… beware. There’s a good chance you’ll be at this for a while, and a couple of headaches are likely in store. It’s not an easy process, but if you can stick through to the end you’ll be happy you gave it a shot.

Using ChronoSync to sync your documents folder

I say we’ll be syncing our documents folder because it’s probably the most straight forward approach to synchronizing, but the reality is that you can really sync anything you want, so long as you have the time to work the kinks out. ChronoSync is known for its ease of use, but it also has some limitations that make this far from the ideal approach. I’ve yet to find one resource to do all my syncing in a way that’s simple and effective, but ChonoSync is one of the the least painless ways to getting your files synced.

Off the top, you should know that your ChronoSync license will work on one computer only, and that you’ll likely also need the Chrono Agent for each of the machines you’re wishing to sync to.

In my setup I have one computer acting like a server, and the rest syncing with it, so I have ChronoSync running on my Mac Pro, and Chrono Agent on my MacBook Pro. Everything I’ve read about ChronoSync tends to illustrate a PC to PC synchronization, and entering a third computer to the mix doesn’t seem like a plausible option (Correct me if I’m wrong), unless you purchase multiple licenses of ChronoSync. So lets get to it then, shall we?

Step 1: Make sure your user accounts Match

The first thing I noticed with ChronoSync is that it’s pretty stubborn. I was trying to sync my user account folders and I couldn’t figure out how to match them up, if they weren’t titled the exact same. Essentially on my Mac Pro my user account shortname is jschnell, and the shortname on my Laptop was jjschnell. I’m not sure what I was smoking so I had to recreate a new user account and migrate my files to it. It’s a bit of a pain in the butt, but it’s possible, so if you’re in the same boat read the next section, but if your accounts are all labelled the same, skip ahead to ‘Setting up the connection’

Step 2: Migrating user’s to a new shortname

There’s no simple way to do this, so you’ll have to go through the process of setting up a new user with the proper short name, then migrating your files. It sounds all well and easy, but it’s not as straight forward as you might expect. I had problems with file permissions for the new account.

From an Admin account, once the new user account is created, copy all the files from one folder to another in ‘Users/’ locations, you can get there by going to the Finder, then clicking on your computer under devices, then the appropriate hard drive, then users. Now copy all the folders from the old account name to the new account name. You’ll probably have to ‘authenticate’ so make sure you enter a admin login and password when prompted.

Now, ideally this would be all set up now, but there’s likely a possibility that you’ll have to give the new user permission to the old users files, as well as assign your administrator account access to the files so that ChronoSync can access the files and sync them. Here’s how you do that.

  1. Once the files are moved to the new account highlight a folder
  2. Right click that folder and click get info
  3. At the very bottom of that window you should see a little lock. Click it
  4. Enter your user name/password (admin account)
  5. Now click the plus button, select the new user account and your admin account (hold the command key and click both.
  6. Push the select button, and they should now be added to the list.
  7. Now we need to change their privileges from Read only to Read & Write. Click the Select Button
  8. Click the Read Only label and then select Read & Write
  9. Now Click the like gear at the bottom and select apply to enclosed items

You should now have access to the proper accounts in ChronoSync, and the user should now have access to the appropriate files. We’re now ready to set up Chrono Sync.

Step 3: Setting up Syncs Using ChronoSync

This is where we finally start to get our syncing on, and can put away all the preparations. Like I mentioned earlier, syncing isn’t very easy yet, so there’s quite a few steps to getting something up and running effectively, chronosync is no different. So, here we go.

After installing ChronoSync on your main computer, and ChronoSync agent on your secondary computer, it’s time to get to setting up ChronoSync to actually do the synchronization.

Setup Tab

Click on the set up tab, and take notice of the layout. It’s referenced a lot through the application. You’ll need to remember which computer you have in the “Left” column, and which computer is in the “Right” column. I prefer having my secondary computer in the Left, and the Main Computer to the right, so from here on out, I’ll be referring to each by it’s location.

  1. Click the drop down list next to Connect To:
  2. Select add/edit/remove connection
  3. Click the Connection tabs
  4. Click te Plus Icon
  5. Now add a profile name, select the appropriate ChonoAgent computer, then fell out the secure connection info
  6. Now you can select your remote computer in the ‘Connect To:’ drop down on the left, and then click the choose button
  7. Select the appropriate folder you want to back up. Note: You’ll want to select the folder just above the actual folder you want to back up. We’ll be able to exclude some folders in a later step.
  8. So, I selected the Users folder
  9. Click the select button

At this point you should see some statistics populate the left column. It’s going to let you know how much storage space is needed for the back up, so you might want to double check that you have the ability to store that much data on your machine. You now want to do the same thing for the right column, keeping in mind that this will be the local machine you’re working on.

Once you have these two targets (columns) set up with your two computers, you’ll want to decide what type of syncing you want to do between the computers. Right in the middle of the UI for the Left Target, and the Right Target, there’s a drop down menu with a bunch of backup scenarios. I’m selecting Synchronize Bidirectional. We want a real, true sync here, so this is going to insure that data from both machines are being moved across the network, instead of data from one machine only. I checked synchronize deletion, because I don’t want to have my files piling up. If you’re a little more paranoid you’ll want to leave this unchecked.

Just to be safe we’re going to save our setup at this point. So click that archaic disk icon, name your file, and hit okay.

To save on time, we’re going to jump to the Analyze tab, skipping over the options, and rules tabs, but I’d recommend looking into them, and seeing if any of the settings there apply to your setup.

Analyze Tab

This is where we’re going to determine what files are being synced, and which folders might be exempt from our process. Again we’re met with a left and right column, and these are referencing the computers and where we placed them in the setup tab. If you forget, you’ll want to double check.

By right clicking on a file or folder, you’ll have a menu that lets you exclude an item from syncing. This is really handy if you’re only syncing a particular folder for a number of users. For instance, I only want my Desktop and Documents folders syncing. I don’t need Applications, and Library folders, as well as music, and movies being synced between my two machines. So I’ve excluded them to speed up my syncing.

Once you’ve set these up you’ll want to save the setup again, and head on over to scheduling the sync.

Scheduling is really straight forward, you pick the day, the hours, and the minutes you want the sync to occur. Keep in mind that the syncing doesn’t act like dropbox, and it doesn’t occur immediately on a file being saved. It’s one of the downfalls of all these syncing methods I’ve tried out. So for me, I have the syncing happening every hour of the day. It’ll stop me from having to manually sync before I use my laptop to get some work done.

Click OK, and you’re done.

You’ll want to save your file again, make sure you backup all the folders and files that you’ll be syncing before you run your first sync, and make use of the Trial Sync in ChronoSync to ensure that your synchronization will go off without a hitch.

Thoughts on ChronoSync

I’m pretty impressed with the application so far, and it’s certainly worth considering it as a syncing option, but there are a number of things that really stood out for me as being a bit of a problem.

It can get pricey. One serial key works on one computer. That’s it. You also have to purchase a ChronoAgent key for all the computer’s you’ll want to have syncing with your main ChronoSync computer. These two things alone make it a bit of a hard pill to swallow; however, it’s probably the most full featured syncing application I’ve come across. So if you’re serious about getting your computers all working on the same page, the price won’t be as difficult to swallow.

When you factor in the abilities to also act as a backup system, the price starts to become a little more palatable. One way syncs, bootable syncs, and bidirectional syncs make this program a full featured backup option. With a little voodoo magic around the operating system, you’ll be able to get away with having one copy of ChronoSync to backup all the computers on your network. Outside of the price considerations, there’s only one other thing that really had me annoyed.

It might just be that I haven’t figured out the proper option to customize my folder syncs, but I found it a little counter intuitive to stop users from being able to sync folders that are not named the same. As I mentioned at the top of this huge post, I had to go to great lengths to make sure that my user account folders were named exactly the same. I couldn’t put the files from the folder jschnell into my folder named jjschnell on a different machine. I can’t see the logic in that. I should have some ability to sync folders that don’t align alphanumerically. I get that some users might make the mistake of syncing folders they don’t want synced, but ‘powerusers’ should have the tools to do this.

On the whole, ChronoSync is worth it if you have a couple of computers to sync across a network, but if you have an entire house filled with Macs, it could get a little pricey. I’d recommend checking out the demo before you run out and purchase the application, just to make sure it’s actually as full featured as you need it to be.

I was going to write about ways to use Rsync for syncing your home folder, but given the length of this article I decided that I’ll save it for a post next week.

Joshua is the Content Marketing Manager at BuySellAds. He’s also the founder of And since all that doesn’t quite give him enough content to wrangle, he’s also a technology journalist in his spare time, with bylines at PCWorld, Macworld… Full Bio