Reading my Instapaper Queue on my Kindle

NOTE: I get a surprising number of people who find this link because they are having problems syncing their Instapaper folders to their Instapaper iPhone app. Even though this posting is not about that problem, I’ve added a section at the bottom that explains how I fixed my syncing issues in the past.

Even with Instapaper, Ramona is not Impressed with my Kindle

Since the release of Apple’s iPad I have viewed it as a device that would serve a very specific use case: reading articles I’ve tagged in Instapaper, while I’m sitting on my couch. My general workflow concerning RSS and information in general is to tag in Instapaper anything that I want to read and then take certain blocks of time where I go through my Instapaper queue. The primary problem with this workflow is that I don’t really like having to sit there, with my computer on my laptop, and just read. Reading, for me, is usually an activity that I like to do with other stimuli either turned off, or a least turned down, and reading on a laptop has never given me that experience. The combination of the LCD screen and the temptation of a keyboard that could easily whisk me off to some other application means that I could never fully get into a reading mode. I hoped that an iPad could change that, but at its current $499 price point, it simply is not in the cards for my student budget. On the other hand, a WiFi only Kindle comes in at a mere $139, which I could make work, but could the Kindle fulfill my reading Instapaper articles on the couch use case?

This isn’t an issue of a comic where I need to keep the big reveal to the end: The Kindle is a great device for catching up on your Instapaper queue. I will give a breakdown of the process that I use to allow for a one click “sync” from all seven of my Instapaper folders to the Kindle. Before I get into that analysis though, a few caveats. The process, as I have created it, is Mac only. I use both Automator and Hazel and I have no idea if there are PC equivalents for those things. My Automator script requires the use of Apple Mail, so you’ll have to have that setup and have it be able to send from an account that your Kindle is configured to receive. Additionally, Hazel is not a free product, so if you want to use this process, you’re going to have purchase it. Finally, I have setup my process to use the WiFi delivery mechanism on my Kindle. If you want to use 3G, then this process will not be free. The cost will vary depending on the size of your Instapaper folders and the articles in them. You will want to check on your Amazon Kindle charge limits before really utilizing this process.

Before delving into how I sync all of my Instapaper folders to my Kindle, it’s important to point out that Instapaper does provide a fairly easy to use system to deliver 20 articles to your Kindle.The instructions are pretty easy to follow and if you don’t mind keeping your Unread items in just your “Read Later” folder, you’re good to go. It’s also useful for those times you’re away from your computer and can’t hit the “one click” necessary to trigger the Kindle sync process (though there are numerous ways to automate the one click process, those are beyond the scope of what I’m going to write here). Also, there are some people who will be fine using the Kindle’s built in web browser to use Instapaper. That might be a perfectly acceptable alternative to show people, but to me, the experience just wasn’t what I was looking for.

The first step in creating the Instapaper-to-Kindle process is writing a brief Automator script that will send the files to your Kindle. Open up Automator and create a new workflow. My workflow looks like this: (1) Get Selected Finder Items, (2) New Mail Message (enter your Kindle email address in the To: field (I used my “free.kindle.com” address since I figured I’d always be on WiFi with my Kindle when I did this), give a subject if you want, and choose an account from the list that you have already setup your Kindle to receive emails from), (3) Add Attachments to Front Message, (4) Send outgoing Messages, and (5) Show Growl Notification (I just titled it “Kindle Files Successfully Sent”). Save your Automator workflow to a location you’ll remember in the next step.

The second step is to create a Hazel rule. You’re going to want to create a rule that operates on your Downloads folder (i.e. the folder where your browser will download items. For me, that’s actually my Downloads folder). The rule is pretty straight forward: If Extension is mobi  then: (1) Run the Automator Script  just created and (2) Move the mobi file to the trash (This last step is probably not necessary but I don’t want a bunch of Kindle files hanging around in my Downloads folder after I’ve already sent them to my Kindle).

At this point, you should be able to go to your Instapaper account and either from your general “Read Later” folder, or from any individual folder, click the “Kindle” icon on the right. This will download the Kindle file to your downloads folder, at which point Hazel will see the the file, call the Automator script that sends the email, and then move the file to the trash. You’ll end up getting the file on your Kindle shortly thereafter. For me, having to click the “Kindle” Icon on each of my folders was still too cumbersome. In order to streamline the process, I created a boomark of link from the Kindle icon for each folder (for Read Later, this is probably http://www.instapaper.com/mobi, while each individual folder will be that link with a /FOLDERID (which is just a number Instapaper assigned to your folder) after it.) I put each of these bookmarks, and just these bookmarks, into a folder of bookmarks in Safari. Now, when I want to sync all my Instapaper folders. I just choose my Safari Bookmark Folder and choose “Open in Tabs”. Safari will then download individual Kindle files for each of my Instapaper folders into my Downloads folder, where Hazel will take over.

The main negative with my process is it’s a one way push. Once I read an article on my Kindle, I have to archive it on Instapaper.com (or the Instapaper iPhone app) if I don’t want that article to show again next time I run my process. This can be an monotonous activity, especially going through all of my folders, but it’s a small price to pay in order to get the reading experience I want on my device.

NOTE: The following is a brief explanation of how I’ve fixed syncing my Instapaper folder to my iPhone application. This has nothing to do with the Kindle process I described above, however, people seem to be looking for that information when they find this posting.

The first question you want to ask yourself when trying to debug your Instapaper syncing is: How long is my Instapaper queue? When I last purged my queue, I must have had more than a thousand items in there, including articles I’d tagged in 2008. This can be problematic when syncing to your iPhone, especially if you have folders you wish to sync. Based on my understanding of how the app does its syncing, it tries to sync the Read Later folder first, and then, if there’s still room under the articles limit you’ve set in your Instapaper app, it syncs the folders (in the order they appear). If you are not getting items synced to your folders, then the first step is to increase your article limit on the app. You do this by clicking Settings in the lower right and scrolling down to “Download”. Up this to 500. If you still do not get items synced to your folders then your “Read Later” queue probably has more than 500 items in it. It might be time to clean some articles out (if you don’t want to just archive them, then moving them to pinboard.in might be a good alternative). If all else fails, Marco’s instapaper twitter account is pretty responsive.