Tutorial — How to sync Instapaper to Obsidian and remember more of what you read online

This article teaches how to synchronise your text highlights from Instapaper to Obsidian on a Mac and iPhone. And to use it for Progressive Summarisation.

Photo by Element5 Digital on Unsplash

Synchronising Instapaper to Obsidian — why on Earth would you want to do that!? For me, it’s all about remembering more of what I read online.

Progressive Summarisation is a great technique to do just that. It’s described in the book Building a Second Brain by Tiago Forte. And in a nutshell, it goes like this: you read an article, highlight passages, and finally make a summary of those passages. So you need decent tools to help you.

My favourite ones is Obsidian for note taking. And Instapaper for reading and highlighting content online. Why?

• Obsidian keeps your text files locally in plain text (no vendor lock-in!)
• Instapaper allows you to export text highlights easily

Unfortunately, Apple users are limited in how to sync Instapaper to Obsidian. But, fear not. There are two neat ways to make this work.

Easy Solution

The easiest solution is to use off-the-shelf tools. You synchronise your Instapaper highlights to the aggregator service Readwise. And then connect Readwise to Obsidian through the official Readwise plugin.

Boom! Bob’s your uncle.

This costs you a few bucks a month, but won’t break the bank.

Fun Solution

The more demanding (and fun!) solution is a bit hacky and a tad cheaper. You extract your text highlights from Instapaper using IFTTT and save them to Dropbox. Then sync Dropbox to iCloud.

What? Wait! What?

Yes. Obsidian for iOS does not support Dropbox. So you need to send the files from Dropbox to iCloud.

Workflow

Here’s the birds-eye-view of the fun solution.

Workflow: Instapaper > IFTTT > Dropbox > Automator > iCloud > Obsidian

1. You highlight a passage in Instapaper
2. IFTTT notices the new highlight and creates a Markdown file (glorified “txt”) with that highlight in Dropbox
3. Dropbox downloads that Markdown file to your Mac
4. Automator moves that file from Dropbox to iCloud
5. iCloud syncs the file to your iPhone
6. You read the Markdown file on your phone

What you need

To make this work, you will need the following accounts:

• Instapaper (free, or $3/month for unlimited highlights)
• Dropbox (free 2GB)
• Apple’s iCloud (free 5GB)
• IFTTT (free)

You will also need the following programs installed:

• Dropbox on your Mac
• Obsidian on your iPhone

#1 Extract highlights

IFTTT is a website that automates workflows. You can use it to do funky things like checking the weather in the morning and alerting you to grab an umbrella. In our case, we will extract article highlights from Instapaper and save them in Dropbox.

To do this, you will create a new automation called applet.

Now go to the IFTTT website and…

1.Click create

2. Click if this

3. A search screen will open. Search for Instapaper and click on the Instapaper icon

4. Click new highlights

5. The following screen will open up. Select your Instapaper account and press create trigger. If your account is not showing, click add new account and follow the step-by-step on screen

6. Click then that

7. A search screen will open. Search for Dropbox and click on the Dropbox icon

8. Click append to a text file

9. Here’s where the magic happens. This screen allows you to customise the file name, content, and location of the file in Dropbox. I would suggest using the article title as the file name. Then append each highlight followed by the article URL, see here:

Now every new Instapaper highlight will be saved in Dropbox — one file per article.

No iPhone? Place your Obsidian vault in Dropbox so it gets the latest files automatically. And you’re done. Kudos.

iPhone user? Read on.

#2 Make highlights accessible on your iPhone

The simplest way is to just manually copy & paste files from Dropbox into iCloud on your Mac. Simple. But boring. 🥱

The fun solution is to automate that task. And Apple’s Automator comes handy here. Automator is a little tool that comes with your Mac to help you automate (duh!) repetitive tasks. In it, you will create a workflow to move the files across.

Remember: we are doing this so Obsidian on your iPhone can read the Markdown files from iCloud

1.Open Automator: Command + Space and type in Automator
2.Select File > New
3.Select Workflow

4.Search Files & folders

5. Now construct a workflow like the one in the example below.
- Find Finder Items is where you select the Search dropdown to identify the Dropbox folder with your Markdown files
- Move Finder Items you select the target folder in iCloud
- Rename Finder Items: Replace Text is to rename the extension .txt (from IFTTT) to .md (so Obsidian on iPhone can read it)

6. File > Save. Make sure you select Application in the File format dropdown

Done.

To run the workflow just double click on Automator application you just created. Or, you can easily make it run every time you start your computer. Simply go to System Preferences > User & Groups > Login Item and add your Automator workflow there.

Happy Progressive Summarisation!