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I’m Simone Silvestroni 👋

I design and code accessible websites since 1998, now using Jekyll and WordPress.

Automation for my static blog publishing workflow

How I’m currently managing writing new content in my Jekyll-based static blog, using Shortcuts on macOS.

Ever since I went live with a redesigned Jekyll-based website, I’ve been looking for ways to improve my publishing workflow. I prefer working with a static website rather than a CMS such as WordPress, yet there are methods to make this process more efficient. This is a work in progress, I’ll be adding new bits to this post in the future.

A few weeks ago I saw a few links posted on Mastodon about the frustrations of maintaining a static web site. Ru Singh argued about the complexity that takes away the pleasure of writing. A couple of follow-ups by Michael Harley, who uses Eleventy, and Luke Harris, who uses Hugo, showed different point of views while still aknowledging similar problems.

I can understand the issues, yet none of them particularly apply to me. However, it’s true that I’ve been honing my process more and more, looking for a way where ideally I would end up clicking an icon or dragging a file into a folder and a few seconds later the post would be ready. Read Taking Shortcuts by Robin Rendle to get what I’m talking about.

I thought about it and asked what are the most annoying parts of writing a new post? Arguably, the answer would be twofold: first, the Front Matter block, which is the top YAML-based section in a static site generator post; second, adding images.

My goals

Streamline the process of writing new posts, where a sort of wizard would guide me throughout compiling all the repetitive bits until an editor appears and I just have to write the content.

Improve the way I add images to a new post as much as I can. What I have in mind is to select one or more images, drag them onto an app and have them:

  • web-friendly renamed;
  • converted to WebP;
  • moved to _assets/images;
  • have a figure “shortcode” ready to be pasted in my post, complete with all the required info: width, height, alt text and caption.

Old method: Sublime Text and Alfred

Before, my automation involved two steps:

  • Creating a new post in Sublime Text using a Jekyll extension capable of creating simple templates.
  • Adding pre-compiled shortcodes using Alfred’s workflows.

It was a good starting point: I obtained a file already named after the post title and today’s date. I still had to manually fill in 6 empty fields in Front Matter. Same thing with Alfred’s shortcodes: handy yet missing vital bits, such as image width and height. After reading Robin’s post I thought I could vastly improve the method using macOS’ new Shortcuts app. I went as far as upgrading my OS to Monterey1.

New method: Shortcuts

I’ve been using Automator for years and I love it. After a couple of days fiddling with Shortcuts I noticed how it doesn’t always agree with me. It looks powerful, yet it sometimes feels buggy2 and convoluted, with a sub-par documentation. As usual with new things, it took me a while to understand how the new app thinks.

As of this writing, I have 3 automation processes that I’m happy about. They are exported as apps in ~/Applications and in my Quick actions contextual menu. A fourth one is still in its infancy and not yet ready.

Local applications folder with custom Shortcuts automation for Jekyll
Local applications folder with custom Shortcuts automation for Jekyll
Quick actions contextual menu showing Shortcuts
Quick actions contextual menu showing Shortcuts

New Jekyll post with Shortcuts

The following short video demonstrates the process in real time.

Here is the whole routine of the wizard:

Shortcuts app for creating a new Jekyll post
Shortcuts app for creating a new Jekyll post


  • 1️⃣ Asks for a post title and sets a variable using the input I provide in a pop-up.
  • 2️⃣ Same for the category.
  • 3️⃣ Same for a couple of tags (I can add more later if I need). It sets a variable containing an array of both my subsequent inputs.
  • 4️⃣ Asks for the description, which goes in my description field in Front Matter, used for SEO purposes.
  • 5️⃣ Same for the excerpt which gets printed below the main heading.
  • 6️⃣ Runs a bash script where the title variable is passed as an argument and does a few things quicker than using native Shortcuts elements:
    • Creates a file in the correct folder, named with today’s date followed by the title variable (in the script I convert spaces with dashes and turn everything lowercase).
    • Adds the Front Matter section and fills it with all the variables I previously created.
    • Launches my markdown editor Typora which opens the file with a compiled Front Matter section.
  • 7️⃣ Runs an AppleScript that opens a minimized session in the Terminal with my alias for running the npm task that holds both Jekyll build and SASS compile actions:
file=$(echo "$( date '+%Y-%m-%d-' )$" | tr " " "-" | tr [:upper:] [:lower:])
touch ~/@ARCHIVE/2022/wwM2M/m2m-website/_posts/"$file" && echo -e "---\ntitle: 'title'\ndate: '$( date '+%Y-%m-%d %T' )'\nlast_modified_at: '$( date '+%Y-%m-%d %T' )'\ncategories:\n  - 'category' \ntags:\ntags \ndescription: 'description'\nexcerpt: 'excerpt'\n---" > ~/@ARCHIVE/2022/wwM2M/m2m-website/_posts/"$file" && open -a "Typora" ~/@ARCHIVE/2022/wwM2M/m2m-website/_posts/"$file"

Adding images to a post with Shortcuts

🚨 Opinionated sidenote — When I used a CMS, I could drag a huge photo to a media library because it would take care of resizing — and maybe optimization through a plug-in or two. Regardless of how much I could streamline that workflow on a CMS, it’s not my cup of tea. I always think about sustainability; the idea of having a website carrying a redundant amount of images is sub-optimal.

The process I follow for adding images to a blog post in Jekyll is made of 5 stages:

  • 1️⃣ Resize and compress so it’s web-safe and as light as possible, usually using GraphicConverter and ImageOptim on macOS.
  • 2️⃣ Rename to a web-friendly format.
  • 3️⃣ Make a .webp version.
  • 4️⃣ Move to the correct folder, in my case _assets/images.
  • 5️⃣ Add width and height to the figure tag.

So far, I’ve manually taken care of the first step. I have a Shortcuts automation in its infancy which is trying to deal with this. If I manage to reach the same level of compression/quality ratio as I do with GraphicConverter, I’ll make the switch.

Even though I tried to manage the whole process with Shortcuts, I have to split the process in two. That’s because I want to still apply steps 2-4 to multiple images, while I prefer to add one image at a time to my post.

Now, the images workflow is reduced to 2 steps:

Renaming and copying images to Jekyll’s assets:

  • Select image(s)
  • Right-click
  • Quick actions
  • M2M images

Inserting new images in a post:

  • Select the image I want to add to my post from _assets/images
  • Right-click
  • Quick actions
  • Jekyll insert figure

I can either right-click and use the quick actions or drag the image to the Dock, where I keep the app version of the same automations.

Video demo


There are 3 pictures on my Desktop, all named incorrectly with wrong spaces and capitalizations:

  • evil CORP.png
  • FRIEND.jpg
  • fux socy.JPG

First, I drag them onto my M2M images app. The app transforms file names into web-friendly versions, replacing spaces and other characters with dashes and turning the file names lowercase. Then it performs a conversion to .webp with a 85% quality factor and finally moves everything to my assets folder.

This is the shell script added at the end:

for f in "$@"
/usr/local/bin/cwebp -q 85 "$f" -o "${f%.*}.webp" && mv "$f" /Users/m2m/@ARCHIVE/2022/wwM2M/m2m-website/assets/images && mv "${f%.*}.webp" /Users/m2m/@ARCHIVE/2022/wwM2M/m2m-website/assets/images

The final action takes the selected image, fetches width and height while asking for alt and caption in a pop-up text prompt:

Shortcut automation for inserting an image in a Jekyll post
Shortcut automation for inserting an image in a Jekyll post

The trick is to collect the required information, store it in variables which I then use to compile my figure Jekyll module in a text block. The output is simply sent to the clipboard, ready to be pasted in my post. From the video, this was the resulting code that I pasted in the editor:

{% include pattern-figure.html image="/assets/images/evil-corp.png" alt="this is the alt" caption="a caption here" width="2560" height="1440" %}

Dynamic content?

I didn’t mention forms and comments: that’s because I don’t need to automate any dynamic content. I have no forms and even if I’ve been planning to ditch Mailchimp and switch to Freelists or manual newsletters, I can easily add a form using Netlify’s functionality3, as Silvia did. I also didn’t want a comment system in the first place, preferring replies via email and W3C‘s webmentions.


In his analysis, Luke has a detailed chapter about how he writes on-the-go or on mobile devices. Again, I’m not elaborating because I never find myself in such a situation. Writing posts is not a urgent activity for me, therefore relying on my computer is enough. Had I been forced to, I’d consider two alternatives:

  • Using micropub with one of the online clients. I have an endpoint, unwisely untested though.
  • Accessing my Github repo and activate VS Code online.


Since the deployment strategy is git-based I don’t think it’s wise to automate this step. I’ve been using either the terminal or Sublime Merge ↗.

Future improvements

  • Polish the new post shell script, for example by switching from tr4 to sed5.
  • Add integration for responsive images.
  • I’d love to port the whole process outside macOS, since I’m planning to move dev work to Linux.
  • Handle the image resize and optimization within Shortcuts, maybe implementing scripts from I’ve already started tinkering with this, see image below:
Shortcuts script for optimizing images
Initial Shortcuts script for optimizing images

I will update this post or create a Part 2 as a follow-up in case I manage to substantially improve the workflow.


So far this methodology has been serving me well. I didn’t mind the previous not-so-dynamic workflow, but I appreciate the value of being helped on repetitive tasks. Especially with images: I’m sure I’ll be tinkering with the scripts until the whole process is consolidated into one precise action.

One thing I really disliked was Apple forcing me to enable iCloud Drive in order to export Shortcuts’ backups on my machine. I don’t see the point other than them trying for the umpteenth time to drag me into their walled garden.

  1. I sorely miss the time when Apple simply released new apps that were available to download on several versions of OS X, but this is a rant for another day. The upgrade went well, unexpectedly fast with no issue whatsoever. I can honestly say it’s behaving better than all the previous OS updates that followed Mavericks. We’ll see. 

  2. Importing workflows from Automator to Shortcuts doesn’t always work, it’s still a hit-and-miss. 

  3. Netlify forms ↗︎ 

  4. tr is a Unix command: an abbreviation of translate or transliterate, indicates its operation of replacing or removing specific characters in its input data set. Read more ↗︎ 

  5. sed (“stream editor”) is a Unix utility that parses and transforms text, using a simple, compact programming language. Read more ↗︎ 

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