Pinboard vs. Raindrop: Two bookmark apps enter…

As many TattleTape readers already know, I live and die by bookmarks. I collect them assiduously, post them to social media (formerly Twitter, now Mastodon) as they pass my gaze, use them in syllabus construction and professional writing, rely on them when people ask me reference-like questions.

Last fall, my mainstay Pinboard did me dirty and I was furious. From the next-to-nothing that was actually communicated to Pinboard users, it appears a DDoS attack caused owner/developer Maciej Cegłowski to cut off access to publicly-available tag pages except to logged-in users. I knew nothing about this until my poor intro students told me they couldn’t reach a tag page (specifically this one) necessary for one of their major assignments. When I went to troubleshoot, I saw no announcement explaining the issue, much less any suggested workarounds.

I’m usually willing to give apps the benefit of the doubt, but not when it harms my students and I can’t fix it for them. Rather than try to remonstrate on Twitter—the Pinboard account there is about Cegłowski and his politics, not actually Pinboard—I went hunting a non-broken alternative. I found Raindrop, did a blessedly quick export/import (good job, both platforms!), and my students were (somewhat haltingly; hold that thought) back in business.

After several months of Raindropping, my conclusion is that both tools are presently awful, but for different reasons. What I’ve done in response is move active bookmarking back to Pinboard, but set up an IFTTT recipe to crosspost all public bookmarks to Raindrop, so my students and I don’t get T-boned by a Pinboard outage again.

Because I not-infrequently get questions about bookmarking tools, following is a wildly opinionated comparison of present-day Pinboard and Raindrop, looking at featureset and user experience. The tl;dr version is that Pinboard is falling apart but its underlying elegance saves it for now, while Raindrop is superficially prettier but the actual experience of using it is full of frustrating warts and friction.

Development status

  • Pinboard: It’s dead, Jim. Pining for the fjords. An ex-service.
  • Raindrop: Active-ish, slowing down?

I don’t think Pinboard’s added a feature in ten years. It certainly hasn’t added a feature useful to me in that space of time. A year or so ago I got some Twitter DMs from someone (not Cegłowski) indicating that a refactoring and new features were on the way, but I have heard nothing since and don’t particularly expect to. Its documentation is similarly stale, and so are its ancillary tools—don’t use the Pinboard-developed bookmarklet for bookmarking because it often breaks and Cegłowski refuses to fix it (blaming browsers and websites instead); get one of the third-party browser plugins.

As for Raindrop, major and minor releases were coming out quite often until last year, when they slowed to nothing. Communication has similarly slowed. I don’t know why, though it may be material that the developer is from Kazakhstan, uncomfortably close to militaristic would-be empire Russia, not to mention that there’s a pandemic on.

I happily suggest to the folks looking to extract people out of the Exploitative Web of Commercial Surveillance to something more humane and open that there’s a giant bookmarking-tool-shaped gap in their stees. Consider building an open-source bookmarking tool with Pinboard’s URL elegance and Raindrop’s visual design. Write the back end in Python and I’d even pitch in.


  • Pinboard: A
  • Raindrop: A

Both these tools are fairly-priced. I can afford them both—and yes, I pay annually for Pinboard’s save-the-page feature—without (much) repining.

URL quality

  • Pinboard: A
  • Raindrop: F

I adore Pinboard’s simple, sensible, elegant URLs. Always have. I can hand-type URLs for any tag or tag combo whenever I want, the system is so easy to remember: u:dsalo (that’s me!) and t:tagname is all I need to know. String together two or three tags? Sure, no problem—and that is a secret weapon of a feature. The only reason this grade isn’t an A+ is that I wish I could add a search string to a URL, something like (to name a specific combo I was hunting for yesterday) and have it work.

Raindrop’s URLs, by contrast, are an absolute dumpster fire. Collections (which are the only “shareable” aggregation in Raindrop) are identified by a lengthy meaningless number-string, not collection name; I haven’t memorized my collections’ numbers and likely won’t. Worse, I can’t copy-and-paste URLs from the address bar because they’re different for the logged-in account owner and anyone else! There’s a whole “share” rigmarole I have to go through to make a collection public, and the eventual URL for it looks like which is just gross. The cherry on top is that hashtags have the hash character… URL-encoded, which is just massively irritating to someone used to Pinboard’s URL elegance. The long and short of it is, Raindrop links are immensely too difficult to repurpose and reuse.

Bookmarking UX

  • Pinboard: C
  • Raindrop: F

Pinboard’s built-in bookmarklet breaks, as discussed above. If it worked reliably, this would be an A grade; the actual bookmarking pane, when it actually appears, is a delight to work with.

Raindrop. Good heavens. Raindrop’s an overclicky nightmare, and is what ultimately drove me back to bookmarking in Pinboard. The Javascripty bookmark widget hasn’t been implemented with the basic common sense to send all available information back to the mothership when the user closes it. I constantly try to close the pane before the widget has saved everything to the server, and fail with a snippy “This page is asking you to confirm that you want to leave — information you’ve entered may not be saved” message. Click out of message, wait wait wait for server to save, click out of widget. This is an awful, wholly unnecessary interaction, one I’d put up with the occasional lost or incomplete bookmark (though neither of those is good, of course) to escape.

Raindrop also has the concept of a “collection,” roughly analogous to Pinboard’s “bundles” (which I don’t use). It’s not a bad idea; it’s just implemented for maximum obnoxiousness in the bookmarking widget. You see, it’s not possible to set a default collection for the widget to use (other than “Uncategorized,” which just makes me itch). In its absence, I have two unappetizing choices: dump everything in Uncategorized and sort it out later, or go through three clicks to set the collection (and risk the abovementioned slow-down-can’t-save interaction) every single time I save a bookmark. This just sucks.

Bookmark-use UX

  • Pinboard: A+
  • Raindrop: F minus-minus-minus-minus-minus and I would give more minuses if I had the patience to type them

Pinboard is once again the pinnacle of spare elegance: tags in reverse-chronological order, good visual information hierarchy in the design of the link display, tags at right for additional tag discovery and refine-further-by-tag, no muss no fuss no frustration. No notes; perfect as-is.

Raindrop displays by very-poorly-implemented “relevance” by default at all times (that is, not just in response to a search, where this might make sense if the implementation weren’t so awful), and this default cannot be changed, so I have to click twice every time I load a Raindrop page to switch to reverse-chronological. What the hell, Raindrop. What even is this nonsense.

But it’s even worse for third parties! If you’re a third party clicking a link to a Raindrop collection shared by its user, you see the entire collection at first. (Yes, have fun trying to scan my 21,000 public bookmarks!) You can refine by searching; if you click in the search box Raindrop pops up a list of tags, which is actually a moderately helpful thing to do. The thing is, once you choose a tag or do a search, that tag list doesn’t go away; you have to scroll through it until you see actual links.

Remember that thing where I have over 900 tags? Yeah. That thing. The way Raindrop handles that thing on shared pages is just unconscionably bad (click image to embiggen and see the full horror):

Raindrop screenshot showing the entire tag list before any links in response to a refine-by-tag search

I had to inflict this on my students, so that they could get to the links for that major assignment. I had to inflict this on my students. I should not have had to inflict this on my students. A pox on both these apps, Pinboard for breaking public pages abruptly and without communication, Raindrop for whatever this absurd excuse for a UI is. It’s just unforgivably bad.

For extra added unfun, the URL to Raindrop’s grotesque monstrosity of a public tag page is I can totally reconstruct that off the top of my head for insertion into a syllabus or Canvas page, right? Yeah, no. No, I absolutely cannot.


  • Pinboard: C+
  • Raindrop: A-

Pinboard’s search autocomplete is overzealous; it sometimes assumes I mean one of my tags when I actually want to search on a phrase that happens to include the tag name, or even another word entirely whose first few letters correspond to the tag name’s. It also doesn’t seem to be possible to combine a tag search with another search term (basically a search using a tag as limiter), something I’d find super-handy. The search response is also abysmally slow sometimes, for reasons I can’t explain.

Raindrop’s search is excellent, by contrast! Combining a tag with a non-tag search term is no problem. It’d be a solid A except that sometimes it gets confused when I refine a search in the search box. The confusion appears tied to the collections system, and the symptom is that the revised search returns no links. Changing which collection is being searched unconfuses Raindrop’s search engine—but again, this shouldn’t have to happen in the first place.

Site speed and responsiveness

  • Pinboard: D
  • Raindrop: A-

Now, I am a Pinboard power user, I admit this—I wouldn’t be surprised to find out I have the most bookmarks or the biggest number of discrete tags (over 900, yeesh) of all Pinboard users. (I also wouldn’t be surprised to find out somebody in fandom has me faded, though. Fandom is hardcore about bookmarks.) As an outlier, I can expect the site to groan a bit dealing with me.

But dang, Pinboard can be painfully slow when I type u:dsalo/t:someTag into the URL bar or do a moderately complex search and turn it loose to load. Five-whole-entire-seconds-to-respond slow. I got in the habit of switching tabs rather than wait for it.

Raindrop is invariably quick to respond—but sometimes a little too quick, as discussed above with respect to search. I’m a fast typist and the fastest bookmarker anywhere; Raindrop gets addled sometimes keeping up with me. I don’t think Pinboard even can get addled.


  • Pinboard: B
  • Raindrop: B-

I can do what I need to do in IFTTT on both platforms. It could be easier, but IFTTT is enough of a power tool that I ain’t super-mad. Raindrop’s hideous URL components and its lack of Pinboard’s public/private bookmark distinction (it can be done, but only with collections, which have serious UX warts) drop its grade by a minus.

Batch tools

  • Pinboard: C
  • Raindrop: C

My kingdom for a usable link deduplicator, on either platform! My other kingdom for a usable tag pruner/refactor-er! I have vastly too many tags and would love to prune some, split others, and move links among tags, but doing so is absolute agony on both Pinboard and Raindrop!

Pinboard has a few useful tools, but they’re buried in account pages. Raindrop has a deduplicator of sorts, but it’s one-set-of-duplicates-at-a-time—relentlessly clicky as usual.

No third-party developers have as yet stepped in to help build more power tools. I wish Spillo would look at this.

So… there you have it. Two tools, alike in villainy. One user, extremely frustrated.