Photo management with Dropbox and Hazel

I recently abandoned iPhoto as a means of storing, organizing and managing photos on OSX and deactivated the associated iCloud Photo Sharing feature running from iOS in to iPhoto via iCloud. I have replaced my iPhoto-based workflow with one centered around Dropbox (which I have subscribed to for some time). I have been asked about this workflow and what follows is a brief explanation of what was involved with setting it up:

I began by exporting my iPhoto library to a folder using Phoshare1. I then created a simple Hazel rule to scan my iPhoto library for duplicate images or videos and discard them. Clearing duplicates from my iPhoto library saved me 6 GB in space which either speaks to how disorganized my library was to begin with or how bloated iPhoto managed to make it.

After clearing duplicate files I created another rule to rename all photos based on the date they were taken and what they were taken with before then organizing them in to a subfolder based on that date. From there organization was simply a question of looking through each folder and appending an event title after the date the folder was named with.

Once all of the above rules were run on my Dropbox Photos directory I edited them to run on my Dropbox Camera Uploads directory. This allows me to upload photos via the iOS Dropbox app or import it directly from my camera and have Hazel auto-organize any content based on event date which I then label and move to a folder in the Photos folder named for the year in which the pictures were taken.

I now have more Dropbox space, an organized and easy to share photo library and a simple workflow for any and all photos I take (I take a lot).

This workflow allows me to keep all my photos (and all of my edited photos) unified across all devices that I use as well as the web. If I need to edit something I edit it in Photoshop and let Dropbox take care of making sure it’s everywhere I need it to be.

To view photos on the go, I use Unbound which allows me to quickly glance through and view images without having to store them directly on the device being used to view them.

I no longer have to wonder whether my photos made it to iPhoto on my MacBook Air through iCloud Photo Sharing or any other device. Any photos I take on my phone are everywhere I need to be without having to worry because of Dropbox, as is the case with any photos I take with my camera (though the process of connecting that to a computer feels increasingly cumbersome).

I’ve seen more complex photo workflows than mine, but tend to prefer the simplicity of the default Dropbox app, a handful of rules and a little manual sorting. Now, I have all of my photos sorted and will have any other photos I take sorted going forward.

You can download the rules I use here »

  1. It’s worth noting that Dropbox’s app also allows you to pull your photos out of iPhoto’s library file. If you import your photos this way, Dropbox attempts to sort them in to folders by date and iPhoto event. I found it easier to use Phoshare as it simply exports your photos in to a single folder, making it easier for Hazel to process them. 

Leaving Google Apps for Fastmail

I recently began a process of re-evaluating the web services I use, the companies that provide them and an evaluation of where I store important data. I had used Google services extensively with Gmail handling my email, my contacts synced through Google contacts, calendars in Google calendar and documents in a Google Drive (I had used Google Reader extensively but switched to a Fever installation following Reader’s demise). While Google’s services are world class, it became increasingly clear to me that if was not in my interest to store significant amounts of personal data with a company that has a financial interest in profiting from that information.

I wanted to replace the free services I was using with comparable services from companies whose interests we’re aligned with their users (whose users were their customers – not advertisers) and who had a clear business model (they provide a service their users pay for).1

Enter Fastmail

I explored several options for email hosting, with Rackspace Email, Hushmail and Hover - email among the services that caught my attention. Ultimately, I landed on FastMail. Fastmail is a reliable, IMAP email provider with extensive support for custom domains. Fastmail also has strong spam prevention and flexible server side filtering.

I began the transition to Fastmail by using IMAP migration tool. The migration process itself was relatively quick too (given the volume of email in my account)2.

While your email is being migrated you should take the time to set up the aliases associated with your Fastmail account. Rather than being tied to a single email address like Google Apps, Fastmail allows you to use virtual aliases that allow you to use multiple email addresses (and even multiple domains) with the same Fastmail account.

During my switch to Fastmail I also took the time to flatten my email folder structure and associated server-side rules. I used to use umbrella folders/labels with individual subfolders/labels for senders within each category. While migrating to Fastmail I elected to keep only the umbrella categories which has allowed me to filter through broadly related emails that have been grouped together rather than tabbing through endless folders. This means I have less fine-grained control over where individual emails go but the time saved in not having to sort through endless subfolders and associated rules has been worth it.

My next step was updating my DNS records at my domain’s registrar and waiting for propagation. Fastmail has extensive documentation on its required settings for custom DNS but, in most cases, you can simply set your MX records to point to Fastmail’s servers:, priority=10, priority=20

You can also point your namer servers to Fastmail as follows:

Additionally, you will need to add an SPF record to your domain’s DNS records as follows:

v=spf1 -all

Finally, you will also need to set up DKIM signing for your outgoing email. Fastmail has instructions on the DKIM setup process on their site. The general steps they provide are as follows:

  1. Login to your FastMail account and go to Options –> Virtual Domains (or Manage –> Domains for a family/business account).
  2. Scroll to the bottom, and you’ll see a new “DKIM signing keys” section. For each domain you have, you’ll see a DKIM public key.
  3. Login to your DNS provider, and create a new TXT record for each domain listed and use the value in the “Public Key” column as the TXT record data to publish.

Contacts and calendars

While Fastmail provides an outstanding email experience, they do not currently support CardDav syncing for contacts (CalDav support is currently in beta ). It is worth noting that Fastmail has an LDAP server that allows you to store contacts associated with your mail account (with an option to add people you correspond with automatically), but the server is read-only.

For now I’m using iCloud to sync my calendars and contacts and will weigh Fastmail’s options for each when full support arrives. I’m currently leaning towards sticking with iCloud rather than adopting Fastmail’s solutions.3 I didn’t, admittedly, explore a host of options for calendar and contact syncing outside of iCloud. I use iCloud for a handful of other things and adopting sync services from yet another party seemed clunky.


Leaving Google Apps also meant leaving Google Hangouts (which I used semi-regularly to communicate with friends and family). Fastmail does offer XMPP support for certain accounts which I have used in place of Google Hangouts. How long Google continues to support XMPP and interoperability with Google Hangouts remains to be seen.

Fastmail so far

I’ve been using Fastmail since the end of November and couldn’t be happier with it. The service has been extremely reliable (I haven’t noticed a single instance of downtime). It’s also been nice to use a traditional IMAP implementation after having used Google’s quirky implementation for so long. Fastmail doesn’t have the host of services Google provides, but it is a bullet proof email provider that I feel I can trust with my data which was exactly what I was looking to in switching4


I did quite a bit of research before switching to Fastmail and the following posts helped push me to make the move:

Have you moved to Fastmail? Are you thinking of doing so? Let me know your thoughts on it or the move to it. You can sign up for Fastmail here.5

  1. My interest in this idea, specifically was sparked by this blog post by Marco Arment: Let us pay for this service so it won’t go down 

  2. I had previously consolidated all of my old email accounts in to my Google Apps account via forwarding and by checking them via IMAP through Gmail. 

  3. I currently use the first-party mail clients on both iOS and OSX so not having contacts and calendars synced with Fastmail is really only an issue when I the Fastmail web interface (which isn’t all that frequently). For now I’ve been manually uploading vCard files to Fastmail which is clunky, but not all that annoying. I do miss being able to create events by clicking on parsed text (which Google Apps supported), but not all that much. 

  4. If you do get tripped up switching from another provider, Fastmail does have extensive documentation. You can also feel free to get in touch with me at @cdransf

  5. This is a referral link so using it will give me credit at Fastmail. 

Changes coming to Droplr »

Droplr began as an idea between two geeks who wanted an easy way to share files with each other. So we set aside some weekends and evenings and built an app that could do just that. Over the last few years what began as a simple free Mac App, has grown into a great company dedicated to creating the best possible way to share files.

If this helps Droplr grow and continue as a successful business, I’m all for it. I use the service daily to shorten links, share files and post images.

Where are you going?

The Fonda Theater marquee in Hollywood.

I’ve been a fan of Godspeed You! Black Emperor since high school and finally got the chance to see them live. The band put on a devastating, energetic performance that was worth the nine or so year wait it took to see them.

Godspeed’s set began with a low, droning noise as the band took the stage, lurching in to a noisy clamor and building to the first of many crescendos. The band played through classic pieces from their discography, silhouetted against a backdrop of Efrim Munick’s rapidly shifting film footage. As the set progressed, members of the band shifted from instrument to instrument, as the sound changed and shifted with them. The performance progressed and grew with the visuals behind the band, developing in to a fully-realized performance piece rather than simply feeling like another concert.

If you get the chance to see Godspeed You! Black Emperor in the future, jump at the chance. They are easily one of the most incredible acts I’ve had the pleasure of seeing live. Brilliant.


  1. Hope Drone
  2. Mladic
  3. Chart #3
  4. World Police and Friendly Fire
  5. Behemoth
  6. The Sad Mafioso

Turns out your kids really did love that music you played »

“The connection to parents’ music isn’t entirely surprising. Music plays a central role in child rearing, both in the songs children are taught at home and in school and in those heard more informally as part of the home environment. The songs parents choose to listen to reflect their taste, their values, their era.”

Great read via NPR. Music means a great deal to me personally and, the older I get, the more I keep going back to the music I listened to with my parents as a kid. There’s nothing quite like re-exploring old songs and albums that helped shape and guide my taste in music to where it is now.