What's New

No More Sitting on “Connecting…”

If you work somewhere with a company firewall, you may have opened the Sidekick panel and watched it say “Connecting…” and never change. Nothing was wrong with your setup, and nothing you did in InDesign would shift it.

The cause was a check for updates that ran before Sidekick opened its connection to InDesign. Most networks answer that check straight away, or turn it down outright. Some company networks do neither — they simply never reply, and Sidekick sat waiting.

It doesn’t wait any more. The connection to InDesign comes first and the update check follows, so a check that goes unanswered can’t hold anything up. Updates that get interrupted now pick up where they left off instead of starting over, which helps on the same unreliable connections. And if a check does fail, ask your AI assistant to run a health check — it will tell you what went wrong rather than leaving you to guess.

Several Assistant Windows, One InDesign

Having a few AI assistant windows open at once is perfectly normal. Only one of them talks to InDesign directly, though, and the others work through it.

If that one went away — you closed the window, or quit it in the middle of something — InDesign could stay out of reach until you restarted everything. The handover now sorts itself out, and the panel reconnects on its own.

A Redesigned Website

The site has been rebuilt around a proper editorial grid and set in a real typeface, and the setup instructions now show the two pieces you need side by side rather than as one long list.

Reviews on the homepage each carry their own star rating, so you can read what individual designers said rather than an average.

Reliability

The rest of this release went into how Sidekick copes when the network is slow, patchy, or blocked — the usual cause of connection trouble — on both Windows and macOS.

Windows Install Fixed for Well-Stocked Computers

If you installed Sidekick on Windows and then typed indesign-sidekick in a terminal only to hear it’s “not recognized” — possibly alongside a small “PATH not updated” message during installation — this release is for you.

The installer’s final step is teaching your terminal where to find the Sidekick command. That step had a hidden limit: on computers where many tools have already claimed a spot on the terminal’s search list — common for people who use Cursor, VS Code or other developer tools, exactly the people connecting Sidekick to assistants beyond Claude — the step quietly gave up. Everything was installed correctly; your terminal just was never told.

The new installer handles a search list of any length, never adds itself twice, and leaves everything already on the list untouched. The fix lives in the installer itself, so it arrives with your next download rather than automatically: if you were affected, download the fresh installer from the install page and run it — your settings and your Adobe Exchange plugin stay as they are.

Follow Releases by RSS

You can now subscribe to these release notes in any feed reader via the What’s New feed. There’s also a plain-text version of the release history, handy for AI assistants and anyone who prefers markdown. Both make the same distinction this page does: changes that reach you automatically versus the rare plugin update that needs a visit to Adobe Exchange.

New Help Articles

Two additions to the help section, straight from real support cases:

• InDesign crashing during AI-assisted table edits — an InDesign quirk, not a Sidekick one, but there’s a simple ground rule that avoids it (and a save-first habit that makes it harmless).
• “Some Sidekick tools are missing” — what to do when the health check, layout or font tools seem to have vanished, and the quick reinstall that brings them back.

Sidekick Can Now Tell You When It’s Time to Update

Most Sidekick improvements arrive on their own — nothing to click, nothing to download. But once in a while a fix lives in the part that’s installed on your computer, and that part can’t update itself. The previous release had exactly such a fix: three tools that assistants had quietly stopped seeing, repaired only by reinstalling. Until now, there was no way to reach the people who needed it — if you didn’t happen to read this page, you’d never know.

That gap is now closed. When a release ships something important that can’t reach you automatically, Sidekick adds one short line to its replies letting Claude (or any other AI assistant) know an update is recommended and why, so it can pass that on to you — at most once a day, with a link to the install page. Updating takes a minute, and your settings and your Adobe Exchange plugin stay as they are.

A few things it will never do: it never installs anything by itself, it never nags mid-conversation (one quiet mention a day at most), and it stays completely silent unless we’ve deliberately marked a release as worth the trouble. Routine updates keep arriving the way they always have — invisibly.

The Missing Tools Are Back

If you ever asked Claude for “sidekick health” and got nothing back — no error, no answer, as though the tool didn’t exist — this release explains it and fixes it.

Every tool Sidekick offers comes with a description of what it does and what it returns, written to follow the specification. In August, the software AI assistants use to talk to tools started validating those descriptions more strictly, and began setting aside a form the specification actually allows — the form three of Sidekick’s tools happened to use: the health check, the layout inspection and the font measurements. Rather than reading them anyway, that stricter check quietly set those three aside before they could ever run. Everything else kept working, which is exactly why this was so hard to spot: nothing failed, three tools simply weren’t there.

This wasn’t specific to Sidekick. The same change took out tools across many unrelated products at the same time, including some of Anthropic’s own. Because the tools are dropped inside the assistant, before any request reaches us, nothing showed up in our diagnostics either — a customer noticing the gap and writing in is what surfaced it.

Sidekick now describes those tools in a different form — equally valid, and one the stricter check accepts — so assistants keep them.

This one needs a reinstall. Most Sidekick updates arrive on their own, but this fix lives in the part that’s installed on your computer rather than the part that updates itself. Download the latest version from the install page and run it — your settings and your Adobe Exchange plugin stay as they are.

Clearer Errors When a Command Is Corrected

Sidekick quietly rewrites common mistakes in the instructions an assistant sends to InDesign, so they work first time. When a rewritten command still failed, though, the assistant only saw the raw error — and would go on to debug the code it wrote, not the corrected code that actually ran.

Failed commands now carry the same notes about what was rewritten as successful ones do. The assistant can see what really happened and fix the right thing, so you spend less time watching it chase the wrong problem.

Also New on the Site

Two new posts on the blog: one on making the maths in your InDesign PDFs readable to screen readers, and one on placing a multi-page engraved music score into InDesign so it takes on the document’s own typeface.

Fewer Failed Commands, Faster Results

When Claude (or any other AI assistant) writes instructions for InDesign, it sometimes uses patterns that look right but don’t work in InDesign’s automation language — the single biggest source of those cryptic errors you may have seen flash by while the assistant retries. Our anonymous error diagnostics showed two mistakes towering over all others: reaching for pages and styles the wrong way, and spelling out style values as plain text where InDesign expects a special value.

Sidekick now catches both and quietly rewrites them into the correct form before InDesign ever sees them. The assistant’s command simply succeeds on the first try, instead of failing, rethinking, and retrying — which means fewer error messages, less waiting, and less of your usage budget spent on retries. In our replay of three months of real-world errors, the majority of the most common failures simply disappear with this update.

Corrections Now Cover Everything

These automatic corrections used to apply only to a hand-picked set of text settings. They now cover every part of InDesign that Sidekick can touch — colors, drop shadows, anchored objects, export settings, and more. Wherever the assistant works, the same safety net is underneath it.

As always, this update applies automatically — there’s nothing to install.

Also New on the Site

You can now reach support directly from the website: a chat widget connects you to the same support inbox as email. And the What’s New page got tidier — the newest releases stay up front, and older ones moved to a new archive page.

Snapshots That Always Arrive

When your AI assistant takes a picture of a page to check its work, that picture can be surprisingly large — especially for pages full of photos or rich detail. AI assistants put a limit on how much data a tool can hand them in one go, and a capture that exceeded it could be quietly discarded by the assistant: Sidekick delivered the picture, but the assistant never took it in, and would report seeing a placeholder instead of your page.

Sidekick now works within those limits: large captures are automatically compressed to a size every assistant accepts, keeping the text on the page crisp and readable. If you’ve ever had Claude (or any other AI assistant) claim it couldn’t see a page it had just captured, this update is for you — it applies automatically, with nothing to install.

Also New on the Site

A help article for the cryptic “_0x5971 is not defined” snapshot error, explaining which installs are affected and the one-time fresh install that fixes it. And the “Sidekick vs. InDesign’s Built-in AI Assistant” comparison has been brought up to date now that Adobe’s Firefly AI Assistant covers InDesign in public beta.

A Clearer Message When Sidekick Can’t Connect

If you opened the Sidekick panel before the Sidekick extension was installed in your AI Assistant, the panel used to say “The AI Assistant was closed. Reopen it to reconnect.” — confusing advice when nothing was ever connected and your AI Assistant was open the whole time.

The panel now says what’s actually going on: “Can’t reach your AI Assistant. Make sure it’s open and has the Sidekick extension installed.” The linked help page walks you through the two quick checks that fix it. This change lives in the InDesign plugin, so it arrives with your next update from Adobe Exchange.

Restarting Your AI Assistant, Properly

The help pages now spell out what “restart your AI Assistant” really means: fully quitting it, with steps for each platform. This matters most on Windows, where closing the Claude Desktop window quietly leaves it running in the system tray — so nothing actually restarts, and no update gets picked up.

Better Insight, Less Data

Sidekick now sends a few anonymous signals — when it starts, when it connects, when a snapshot is taken — so we can catch problems before you have to email us about them. At the same time we’ve tightened what we keep: IP addresses and location data are no longer stored with any telemetry, and the privacy policy has been updated to describe exactly what’s collected. Telemetry can be switched off anytime by asking your AI Assistant to “disable Sidekick telemetry”.

Also New on the Site

A help article for schools hitting Adobe Exchange’s “Plugins are unavailable for your user type” restriction on K-12 accounts, and a blog post on auditing alt text in your documents with Sidekick.