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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.

Windows Fix

Sidekick now starts reliably on Windows with Claude Desktop. If you installed recently and saw “Server disconnected” — or the panel sat on “Connecting…” and never got further — this release fixes it. Nothing was wrong with your connection or your setup: Sidekick downloaded everything correctly and then couldn’t find its own files again.

If you’re on Windows and hit this, reinstall the Sidekick extension in Claude Desktop once and you should be up and running. Sidekick will pick up where it left off without downloading anything again.

Automatic Updates on Windows

This one is bigger than it sounds. Sidekick updates itself in the background so you always have the latest version — except on Windows, where that had quietly never worked. Windows users have been running the version that shipped with their extension, missing every improvement since.

That’s fixed. Once you’re on this release, Windows gets the same automatic updates macOS has always had. You’ll also reclaim some disk space: old versions were piling up unnoticed, and Sidekick now tidies them away.

Installer Fix

Fixed an issue where the one-click installer (.mcpb) would fail with “Could not download Sidekick” on fresh installations or when the cache was cleared. The installer now correctly downloads the required files in all cases.

This release includes changes from 1.0.17 and 1.0.18 that were not previously available.

Smarter Object Snapshots

When you ask your AI assistant to capture a small object (smaller than about 3 inches), InDesign adds padding around it. Sidekick now automatically crops away this extra whitespace, giving you a clean, tight capture of just the object you wanted.

The snapshots are also compressed to stay within size limits, so you can capture more content in a single conversation.

Simpler Installation

Sidekick no longer requires native image processing libraries. This means:

• Faster, more reliable installation
• No platform-specific dependencies
• Works consistently across macOS and Windows

The connector now handles all image processing internally, so there’s nothing extra to install or configure.

See Snapshots Right in the Chat

When you ask Claude (or any other AI assistant) to show you how something looks in InDesign, the snapshot now appears as a full preview right in the conversation — fit it to width or zoom in to inspect the detail — instead of being tucked away inside a collapsed tool panel.

The snapshots Claude takes purely to check its own work stay quiet, so the chat doesn’t fill up with verification images — you only see the ones meant for you.

Sharper, More Accurate Object Snapshots

When Claude captures a single object to review it — for example to write alt text or confirm a change — that snapshot is now accurate even for trickier artwork:

• Rotated and transformed objects are captured exactly where they sit on the page, instead of from the wrong area.
• Objects on a background — like a cover sitting on a colored poster — now show that background through any gaps, rather than blank white.
• Overlapping elements are layered in the right order, so what Claude sees matches what’s actually on the page.

This makes Claude’s review of your layout more trustworthy, which is especially handy for systematic work like checking images one by one.

A Closer Look at Your Document

When Claude (or any other AI assistant) makes a change in InDesign, it likes to glance at the result. Until now that glance was a whole‑page view at a fairly coarse resolution — fine for confirming “the block moved,” but not “is this exactly right,” because the details that decide right are small.

Sidekick can now look much closer:

• Sharper full‑page views. Pages and spreads are rendered at the resolution a vision model can actually use, so fine type and the content inside image frames come through instead of blurring away.
• Zoom into any area. Claude can capture just part of a page at full detail — handy for reading a caption, a hairline rule, or whether the logo in the corner is the right one.
• Inspect a single object. Claude can look at one image or frame on its own — ideal for systematic work like checking or writing alt text image by image.
• Quick preview mode. A cheap, low‑resolution snapshot for fast “did the layout roughly change” checks when detail isn’t needed.

It all happens automatically — Claude chooses the right resolution for what it needs to see, and there’s no plugin update required.

Smoother Install in Safari

Downloading the Sidekick installer in Safari used to unpack it into a folder, which could trip up setup. It now downloads as a single file, so installation is one clean step.

Reliable Snapshots

Snapshots used to fail on documents that use section prefixes (such as “A‑1” style page numbering), and asking for a spread only captured its first page. Now snapshots work whatever your page numbering, multi‑page spreads come back as a single joined image, and when an export does fail you’ll see the actual reason rather than a generic error.

Smarter Connection Health

When something isn’t working, asking Claude (or any other AI assistant) to run “sidekick health” now does a real live check instead of reporting what it remembered from when it started. It tells you whether commands are actually getting through, which part of the connection is failing, how long it’s been running, and when it last worked — so connection problems are much quicker to track down.

More Reliable Reconnection

Previously, a brief hiccup between Sidekick and your AI assistant could leave the panel permanently stuck on “Update required” — even when nothing was actually wrong. Sidekick now recovers from these transient drops on its own and stays on a stable “Connecting…” state until the connection comes back.

Clearer Connection Messages

When the panel can’t reach your AI assistant, you’ll now see a plain-English description of what’s happening — for example, “The AI Assistant isn’t responding. Try restarting it.” — along with a Learn more → link to a help article for that specific situation. No more cryptic jargon when things go wrong.

Crash Diagnostics

Previously, certain errors could cause Sidekick to stop working silently — with no indication of what went wrong. Now these errors are caught and logged, making it much easier to diagnose connection issues.

Smarter Code Handling

When your AI assistant writes code for InDesign, Sidekick now automatically fixes a common mistake that could cause errors. This means fewer failed attempts and smoother workflows.

Cleaner Updates

Sidekick now cleans up old versions after installing updates, keeping your system tidy.

Better Connection Diagnostics

When something goes wrong with the connection between Claude Desktop and InDesign, the logs now capture much more detail about what happened. This helps us troubleshoot issues faster — especially on Windows setups where connections can be tricky.

Usage Statistics

Sidekick now tracks basic session statistics (like how many operations succeeded or failed) to help us identify and fix reliability issues. No document content is ever collected — just aggregate counts. You can disable this by asking your AI assistant to “disable Sidekick telemetry”.

Improved Error Tracking

We’ve enhanced our anonymous telemetry to better understand how Sidekick is performing. This helps us identify and fix issues faster, ensuring a smoother experience for everyone.

As always, telemetry contains no document content and can be disabled by asking your AI assistant to “disable Sidekick telemetry”.

Fewer Failed Attempts

You may have noticed that Claude (or your favorite AI assistant) sometimes needs a few tries to get things right in InDesign. We’ve added more guardrails to catch common mistakes before they happen.

The result: your AI assistant stays on track more often, so you spend less time waiting for retries and more time on your creative work.

Font Metrics Reliability

Fixed an issue where the font metrics tool could fail to read your installed fonts. Claude can now reliably measure font characteristics like x-height and cap-height for precise text positioning.

Claude Desktop Compatibility

Improved how Sidekick communicates with Claude Desktop to follow the latest MCP protocol standards. This fixes an error some users saw about “structured content” when using certain tools.

Image Placement

You can now place images directly into your InDesign documents. Just tell Claude (or any other AI assistant) where to find an image on your computer, and Sidekick will add it to your layout.

For example, you can say “Place the logo from my Desktop into the header” and Sidekick will create an image frame and insert your file.

Note: When you update the plugin, you’ll see a permission prompt asking for file system access. This is required so Sidekick can read image files from your computer.

Error Telemetry

Sidekick now sends anonymous error data when code execution fails in InDesign. This helps us identify and fix common issues that users encounter.

What’s captured: Error messages, code snippets (first 500 characters), and version information. No document content is ever captured, and all data is anonymous.

Easy opt-out: Just ask Claude to “disable Sidekick telemetry” and it will turn off error reporting.

Configuration Tools

You can now ask Claude about Sidekick’s settings using the new configuration tools. Currently this lets you view and toggle the telemetry setting, with more options planned for future releases.

Font Cache Fix

When using refresh=true with the font metrics tool, the cache is now properly cleared. Previously, stale font data could persist even after requesting a refresh.

Website Blog

The Sidekick website now has a blog with articles about getting the most out of Sidekick. The first post covers how Sidekick can read font metrics that are normally inaccessible through InDesign scripting.

Font Metrics Fix

The font metrics feature introduced in v1.0.4 had an issue that prevented it from working in some environments. This has been fixed, so Claude can now reliably measure fonts for precise text positioning.

We’ve also added automated testing to catch similar issues before they reach you.

Font Metrics

Claude can now read detailed font measurements like x-height, cap-height, ascender, and descender heights. This helps position text more precisely, especially when aligning text to baselines or creating typographic grids.

The connector supports fonts from your system fonts folder and Adobe Fonts. Font measurements are cached locally for faster lookups after the first scan.

Update Notifications

When Sidekick downloads and applies an update while you’re working, you’ll now see a notification in Claude Desktop’s server panel showing the old and new version numbers. This keeps you informed about new features and fixes as they become available.

What’s New Page

The Sidekick website now has a What’s New page showing user-friendly descriptions of each release. You’re reading it right now!

Better Tool Discovery

The connector now correctly signals that it provides tools dynamically. This improves compatibility with MCP clients that automatically discover available tools.

Better Object Naming

When Claude creates objects in InDesign (text frames, shapes, etc.), they now get meaningful names that appear in the Layers panel. This makes it easier to find and select objects that Sidekick created.

Previously, objects were named generically. Now they get descriptive names like “Header Text Frame” that tell you what they are.

First Stable Release

Sidekick for InDesign is ready for production use. This release marks the first stable version of both the connector and the InDesign plugin.

With Sidekick, Claude can now control Adobe InDesign directly - creating documents, placing text, adjusting layouts, and more.