Converting to M1 Mac - very old jekyll 2.5.3

My site, has been built with jekyll 2.5.3 since that version was new. My old iMac self-destructed, and so i need to build on a new M1 Air. After long travail too tedious to mention, i have it working on 2.5.3 jekyll and the 2.6.2 built-in Ruby, with one exception: i had to remove the ancient plugin kramdown-with-pygments, so i’ve lost syntax coloring. Anyway, I’m alive enough to keep afloat.

I tried “just” installing jekyll 4.x this morning and the build crashed (literal ruby crash), so i just went back to 2.5.3.

a big issue with getting to 4.x is that my installation has substantial plugins, which create category and tag indexes. perhaps jekyll today could do that, i don’t know. i’d like to accomplish two things:

  • get syntax coloring back
  • get up to a more current version, ideally 4.x.

I am very rusty on jekyll and ruby, and would be open to paid help (i.e. do it) for the latter task. i’m want someone with an m-chip mac, obviously.

and, of course, any smaller-scale help here will be most welcome.



Hi Ron,

While I am sure there are people on here that would be happy to do the paid work, we can also help if you post some more granular questions.

In my experience, a lot of the plugins for Jekyll are pretty basic and are easily replaced with a few extra lines of code. For example, the SEO plugin is not much more than some variables you place in the <head> element of your site. This is not to say plugins are not valuable, but with a little extra hand-coding you can probably do it yourself.

As for getting set up on the M1, there are a good number of posts where people have asked that question and I think most got it sorted out, so you might want to read up. Also, make sure you follow the Jekyll instructions on the Jekyll docs site.

Also, I could be wrong, but am pretty sure Jekyll uses Kramdown and Rouge now, so maybe that could be a good starting point for your code highlighting? Unfortunately, I have little experience using code highlighting because most of my posts are for podcasts and not code.

Anyway, if you ask the question, share your public repo (GitHub, GitLab, etc) and your website and point out the problem you are trying to address, we might be able to help you.

Hi Bill,

I’m starting to dig thru the M1 posts, and will see what i can share if need be. my site has hundreds of pages, gigs of storage, years of material. the site, on 2.5.3 for years, used kramdown and pigments. i tried to go all the way to 4.x but got the ruby crash. i’ll see if a version 3 can be made to run.

When i get to real questions, i’ll try to be usefully specific.



If your code is on a public repo I would be happy to run it on my 4.2.0 instance for you and give you some overall feedback.

It’s private but I’d be happy to invite you to it. Please don’t change it. :slight_smile: Let me know what email to admit at Warning: it is HUGE.



Good News! A colleague helped me convert all the way from 2.5.3 to 4.2! Had to remove one plug-in for syntax highlighting, and remove two render-all from other plugins, replacing with super. A small change to config, and including webrick, and poof!

A great credit to the Jekyll team for retaining this much compatibility across so many versions!

I am a happy camper!




I’m thrilled that this upgrade had such a successful outcome for you and that our work to ensure as much backwards compatibility as possible is appreciated.


Great news! Glad it went well and you are all set!

I’ve tossed a tip into the bucket as a token of my appreciation. Even so, it’s probably less than you deserve. Good stuff, thanks!