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I picked up a Kindle mostly to help aleviate my huge backlog of unread Instapaper articles - well over 600 (!).

What I'm hoping to figure out is the best practice to sync new unread articles to my Kindle - and figure that I'll have to use software for the time being until Instapaper's built-in Kindle syncing improves.

Here are some syncing methods I've come across so far and in italics my experiences with them:

1) Use the built-in support within Instapaper to wireless transfer bundles of new unread articles to my Kindle email address, OR use the .mobi link provided via and transfer this file via USB

This will send new articles (up to the 20 most recent) but doesn't send anything older than the most recent 20, and doesn't sync back to archive a read article once it's been read*

2) Use user created software such as Ephemera (OS X) or Wordcycler (Windows)

These tools are basically designed to do exactly what I am looking for, including articles on Instapaper once they are deleted off the Kindle - HOWEVER they don't seem to support such a large backlog of articles - which may be the Instapaper API timing out

3) Browse via the built in browser (and use article mode)

This so far seems to be the most manageable but only when there is a wifi or 3G connection. Biggest downside seems to be that the Kindle browser is really sluggish when navigating the Instapaper site (likely because I have such a large queue that it has to parse)

4) Use Calibre to download or send articles

Doesn't seem to support syncing back once articles are read

This is a software related question - I am hoping for an ideal software solution until Instapaper and/or the Kindle provide a better official workflow in the future.

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You seem to have made a clean sweep of all the existing options.

The following article uses the products you already mentioned, but maybe in a different way:
Web content & PDFs – Instapaper & Kindle Miracle Solution.

It might give you a slightly different angle on the problem, especially as it uses dropbox as the pipeline. One might be able to figure out how to use dropbox for the reverse sync, but that requires hands-on experience with the above tools (which I don't have).

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I think the only benefit this workflow provides is parsing PDFs with Instapaper and allowing them to be easily read on the Kindle. Doesn't address the main issue I'm having which is loading such a large backlog onto the Kindle. – Josh Newman Dec 9 '10 at 17:37
Link is broken, here's a working one:… – molgar Aug 18 '11 at 12:05

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