Chris Dzombak

From Pinboard to Raindrop

I’m on record as having been a fan of Pinboard in the past. This has changed and, effective yesterday, I’ve migrated to using for bookmarks instead. This post describes my rationale for the change, discusses my experience thus far with Raindrop, and outlines what I’d really like from a bookmarking application.

Why not Pinboard?

Pinboard has lacked any updates (feature, design, or otherwise) for … I don’t even know, probably the better part of a decade now. And there have been some recent annoying periods of downtime. But that wasn’t enough to get me to migrate away from it; inertia is difficult to overcome.

In October 2021 I received the following email:


Please note that archiving for your Pinboard account (cdzombak) has been turned off for lack of payment.

This means Pinboard will no longer store cached copies of your bookmarks, and you will not be able to do full-text search. Any archived content for your account will be deleted.

Apart from those features your account is still completely functional, and I hope you’ll keep using it!

If you change your mind about archiving (or if you still want to renew) you can upgrade at any time by visiting The archiving feature costs $39/year, with discounts for multiple years.

Please don’t hesitate to contact me by email ( with any questions, and thanks as ever for using Pinboard!

Kind regards,

Maciej Ceglowski

I had received zero notice that payment was needed. I paid $95 in 2016 for an extended period of archiving. (Of course, Pinboard being Pinboard, I can find no receipt reflecting exactly what I bought; this dollar amount comes from a credit card notification about the purchase.) Since then, my Pinboard account page showed something like “don’t worry, you’re all set” when I tried to see when my account’s archiving feature would expire. The correct answer was “October 7, 2021, but I’m not going to tell you in advance.”

I replied to that email the next day asking whether, if I paid immediately, all archived content would be preserved, and never heard back. I followed up via email a few more times over the next month, and also tried to get in touch with Maciej on Twitter, but heard nothing back.

I opted not to renew the feature, because for $39/year I expect something better than “your archiving account was turned off with zero notice, all archived content has been deleted, and the site’s owner is too busy tweeting about politics to provide literally any acknowledgement that his customers exist.”

Speaking of Twitter:

The thing where bien-pensant people are required to pretend J.K. Rowling hates transgender people is one of the weirder cultural phenomena of the early 2020’s.

Like, I read what she wrote and found it thoughtful and argued in good faith. Readers might disagree (even vehemently), but where is the malice or anti-trans hate in this document?

Maciej Ceglowski (@Pinboard) on Twitter, Feb. 22, 2023

You can read the rest of the thread if you really want. He’s pretty committed to the “just asking questions; I read one thing and it seems like JK Rowling doesn’t hate trans people” contrarian bit.

Okay, fuck that guy. How’s Raindrop?

Raindrop seems fine. Pretty good, even.

It imported all my Pinboard bookmarks and metadata correctly from a JSON export. The Raindrop UX across platforms is pretty good. It’s not stellar, but I think it’s significantly better than Pinboard’s. Having a supported, first-party iOS app is a huge plus.

It’s not a 1:1 Pinboard replacement (this post goes over some relevant differences, though I don’t agree with all the letter grades assigned in it), but (1) I didn’t find a solid 1:1 replacement and (2) I’m not sure I actually want one.

I didn’t find a solid 1:1 replacement

I didn’t do a very thorough search, to be sure, but I think “ replacement” is niche enough that there aren’t many to choose from. Raindrop seems to be the most polished product, and it’s the one I’ve heard mentioned in the same context as Pinboard the most often.

There also might be some open-source alternatives in various states of completion that I’d need to self-host, but I’m not interested in evaluating and hosting those right now. (If a solid self-hostable open-source Raindrop alternative shows up, I’d be interested — more on that later.)

I don’t think I want a 1:1 replacement

This situation prompted me to think about my Pinboard usage pattern for the past 5 years or so.

I write stuff into it that I find interesting or “might want to look at later” but I effectively never actually refer back to it, by tags or otherwise.

At the same time, my tagging philosophy and tag naming conventions have drifted so much since I started using del.icio.us1 that my ~4000 Pinboard tags were an inconsistent, unusable mess. And Pinboard’s search is not good.

So with Raindrop I’ve decided to give up on nearly all tags2. I hope to rely instead on search, Gmail-style. I think this will make adding bookmarks less stressful — no need to think about “what tag did I use for this sort of thing 7 years ago” — and having a useful search should make it more likely I’ll actually refer back to my bookmarks collection

So far this seems to work well enough. I’m paying for Raindrop’s Pro plan, which includes full text search of all bookmarks. (I don’t think any Pinboard plan includes that.) It also includes the “Permanent Library” feature, an equivalent to Pinboard’s archiving function.

I’m also putting new bookmarks into one of a very few collections3, but I expect bookmark lookups to be almost exclusively by search.

Things I miss doesn’t do “social.”

Each individual bookmark in Pinboard is either public or private. In Raindrop, you can make a collection public, but not an individual bookmark. Each bookmark can only exist in one collection, and copying a bookmark to another collection is clumsy.

This isn’t great. I certainly want my collections to be private by default, but ideally I could share some of the bookmarks in each. I’d love to see Raindrop allow making individual bookmarks public. (I have a public collection, but there’s effectively nothing in it right now, because I’m not sure how to use it vs. my other collections.)

Raindrop could even allow making all bookmarks with a specific tag public, which would work here, since tags exist across collections.

An ideal tool

Raindrop is pretty good, but here’s a brief list of what I’d love to see as a Pinboard replacement:



You can find my public bookmarks collection here.

  1. Of course, my tags got migrated to Pinboard when I migrated away from 

  2. If you have several thousand tags, bulk deleting all but a few of them in the Raindrop UI is theoretically possible but extremely tedious. I wrote a tool to do this for me. One day I might even write documentation for it. 

  3. My collections in Raindrop include broad themes like “Birding,” “Dev,” and “Photography.” The goal is to keep them broad but distinct enough that I never have to think about which one a bookmark fits into.