What IT Is

TL;DR: The Sprint Retrospective would be the most valuable ceremony in Scrum…if it weren’t also the one with the worst follow-through. AI can run the same ceremony and actually keep the results, because the lesson gets loaded before the next session instead of filed and forgotten. It’s a simple habit to learn, and there are plenty of free examples of how to automate it. It’s a small investment of time and thought that pays real dividends in productivity and confidence.

The Ceremony That Everyone Likes and Nobody Finishes

The 2020 Scrum Guide puts the Sprint Retrospective at the end of the Sprint, timeboxed to three hours for a one-month Sprint (not that many places do one-month Sprints anymore, or allot three hours for improving things). The process is simple: provide a safe space where people can speak their mind about what went well, what didn’t, and how they would change things to be better in the next Sprint. The goal is to capture ways to increase quality and effectiveness while reducing friction and wasted time.

In theory it’s the smartest ceremony of any SDLC. A room full of people who just lived through the same thing, comparing notes while it’s fresh, with permission to say what actually happened.

I was introduced to this ceremony before Agile approaches were common in the enterprise. We ran it after a major release, and I found the process very enlightening. Someone wrote up a summary of the findings and posted it on the company intranet.

This was a long time ago. Years later I remembered that document and got curious about whether anyone had ever gone back to it.

I was the only one who ever looked at it again.

I can’t recall a single piece of wisdom it captured. Not one. What I do remember is the aura of “this makes so much sense” when we discussed the stickies on the wall. And that the same mistakes were repeated across later projects, many with some of the same people in the room who had sat through the meeting where we agreed not to make them again. Sigh.

What Happens to the Findings

Follow the output and the pattern is easy to see.

Some items become real assignments. Someone owns it, someone completes it, and the team is measurably better off. That’s a real win and it’s worth saying so.

The problem is, it is too often a one-off win. The task closes. It’s checked off and moved to Done. Then the same thing comes up three Sprints later. Or the next Sprint.

Because the good stuff that gets surfaced in a retro isn’t something that can be fixed with a story. It’s a lesson. “We committed before we understood the integration.” “We let the staging environment drift.” “We assumed the client would review in three days and they took three weeks.” Those aren’t tickets. They’re rules for how to behave next time, and there is nowhere to put them where people will remember them (yes, there’s an exception, for those who are already ahead of the game with a living PROJECT.md, aka CLAUDE.md, AGENTS.md, or whatever your favorite harness uses).

So they go into a document. Which goes onto an intranet page. Which nobody opens during the next project, because during the next project everyone is busy doing the next project.

The retrospective produces knowledge with no delivery mechanism. Six weeks later a new team, or the same team with two new people, walks into the identical wall and holds an identical meeting about it. We call that continuous improvement. It’s closer to continuous rediscovery.

That failure, organizations not learning from their own experience even after making the capture of lessons a required part of the process, is a big part of why the Best Practices section on this site exists at all.

Run the Same Ceremony, by Hand

Now try it with AI at the end of a working session. At its most basic, this is two prompts.

Review this session. What worked, what didn't, what should change next time?
Give it to me as Start, Stop, Continue.

Start doing this, stop doing that, keep doing this other thing. Read what comes back, edit anything that’s wrong or too vague to act on, then:

Save that to memory and apply it going forward.

That’s the entire ceremony. Under two minutes, no tooling, no setup. (YMMV on the prompt, depending on your type and style of work…BWTM)

Here’s the part that changes everything. It doesn’t file the lesson. It applies it, every time, forever. Next session, and every session after that, those rules are loaded before the first word of work gets done. There is no folder, no onboarding deck, no hoping somebody remembers. The correction is simply in effect.

And it updates. Session ten refines what session three concluded. A rule that turned out to be wrong gets replaced instead of quietly ignored.

Same ceremony. Same format. The difference is entirely in what happens after the meeting ends.

The productivity gain is obvious enough. The part that sneaks up on you is the confidence. After a few weeks you stop bracing for the mistake you already corrected once, because it doesn’t come back.

The Gap Was Never Honesty

The lesson here isn’t that AI is disciplined and people are sloppy. People are perfectly capable of discipline. What people don’t have is a place to put a lesson where it will find them again at the moment they need it.

That’s the gap the retrospective has always had. Not insight. Distribution.

AI closes it almost by accident, because persistent memory is just how the thing works. The lesson arrives in the same channel as the work, automatically. You don’t have to remember to go check.

Which reframes a lot of process failures. Most of the time the problem isn’t that we didn’t learn. It’s that the learning had no route back into the work.

Almost Nobody Does This

Here’s the honest part. Very few people take the time to run a retrospective on their AI sessions, and fewer still do it consistently.

It isn’t hard and it isn’t slow, which is exactly what makes it easy to skip. Two minutes is nothing. Two minutes you never spend is also nothing, and it’s what most people land on by about the third busy week. The ceremony that depends on remembering to hold it is the ceremony that quietly stops happening, which is the same failure mode as the intranet page, just faster.

That’s the argument for automating the capture rather than relying on the habit.

You Don’t Have to Invent This

Run it by hand for a few weeks first, though. You want a feel for what a useful captured lesson looks like before you hand the job to something that writes them without asking, because you’ll be reviewing that output later and you need to be able to spot a bad one. Automated capture drifts. It records the frustrated aside instead of the actual rule, or it generalizes a one-off into a standing instruction. Doing it manually first is how you learn to recognize that when you see it.

And you don’t have to tune that prompt from scratch, or build the automation yourself either. There’s an entire cottage industry of shared instruction sets, skills, and rule files built to automate this loop, and most of them are free and MIT-licensed. Read a few and you’ll find better phrasing than mine sitting right there in someone’s repo.

claude-reflect is the most widely adopted of the ones I found. Hooks watch your prompts for correction patterns like “no, use X” or “actually” and queue them automatically. You then run a command to review the queue and approve what gets written into your persistent instructions. Capture is automatic, application requires your sign-off. It also mines your session history for repeated requests and offers to turn them into reusable commands.

bokan’s self-improvement skill takes a different angle: it fans out parallel agents across your past sessions, ranks friction patterns by how often they recur, and attaches the raw quote where things went sideways. Frequency plus evidence, which makes the finding arguable rather than just asserted.

claude-improve is worth reading even if you never install it, because its README openly credits the six community approaches it was assembled from. One of those, a one-prompt reflection pattern, contributes the single most practical idea in the whole space: write the captured lesson as an enforceable rule. Lead with why, use NEVER and ALWAYS, include a concrete example. Most captured lessons fail because they’re written as vague observations that nothing can act on.

Cursor users have the same pattern in a different wrapper, usually a self_improve.mdc rule paired with a rules file, as described in Stop Babysitting your AI.

Pick one, use it as-is, or read three of them and build the version that fits how you actually work. Standing on someone else’s structure beats staring at a blank file.

What the Evidence Says

One thing to calibrate before you go shopping, because I’d rather say it than have you find out later.

None of these tools has been independently reviewed or benchmarked. What they have is stars, forks, and enthusiastic author write-ups. A thousand stars measures whether an idea sounds good, not whether it works. There’s no head-to-head comparison, so pick on fit rather than on popularity.

The underlying mechanic, though, has real support. The Reflexion paper from NeurIPS 2023 found that agents that write a short natural-language reflection on what went wrong outperform agents that store the raw record of what happened by eight percentage points absolute. Storing the transcript is worth less than storing the conclusion. That is the academic version of Start, Stop, Continue.

Anthropic’s own context management benchmark reports a 39% performance improvement over baseline when memory and context editing are combined, and 84% fewer tokens consumed on a long multi-step task. Vendor-run, so discount it accordingly, but it’s a real evaluation with published numbers.

The mechanism is sound. The specific tooling is a matter of taste.

Prune It, or You’ve Just Rebuilt the Intranet Page

The one part none of this tooling can do for you: every system here accumulates rules, and none of them has a convincing answer for pruning. claude-reflect ships a dedupe command, which tells you the problem is real enough to need a command.

So budget a few minutes every month or so to read what’s piled up and delete what’s gone stale. That’s the intervention the manual practice trained you for. A memory file nobody audits becomes the same dead document, except this one is actively steering your work instead of quietly sitting on an intranet.

Making the Time Before You Save the Time

All of this runs into the oldest problem in efficiency work: you have to spend the time before you get the time. Every initiative that eventually saves hours starts by costing hours you didn’t have when you decided to do it. Automating your retrospectives is no different. The build is small, but it’s still a build, and it competes with the actual work that made you want the efficiency in the first place.

I get it. New habits are hard. I confess that I don’t do this as regularly as I should, and that even though I have some prompts pre-written in UpNote to use that are more involved than the example given in this post, I usually write one off the cuff when I do remember. Maybe if I spent less time writing about techniques and more time automating them…

Which is exactly why the two-prompt version matters. It costs nothing to start, it works on its own, and it buys you the judgment you’ll need before you spend an afternoon wiring up anything fancier. Start there. Automate when the habit is annoying you enough to be worth removing.

An Answer to the Question Everyone Keeps Asking

“What are we doing with the time we save using AI?”

Fair question, and most of the answers are vapor. Here’s one that isn’t.

Spend a slice of it teaching the tool what it just learned. Those two minutes are the highest-leverage part of the whole workflow, because they’re the only part that compounds. Every other minute you save gets saved once. This one gets saved again on every future session.

It shouldn’t take all of it. And it should take less as time goes on, which is the tell that it’s working. Early sessions produce a lot of corrections because there’s a lot the tool doesn’t know about how you work. Later sessions produce a few refinements. Eventually you’re mostly confirming that the rules still hold.

Use the rest to go touch grass.

That’s not a throwaway. The entire argument for this technology is that it gives us capacity back. If we spend all of the reclaimed time on more work, we didn’t gain capacity, we just raised the quota.

Now Tell Me What You’re Actually Doing

This is the part where a post like this usually promises a follow-up with results. I’d rather ask than promise.

If you’re already running some version of this, I want to hear it. Which tool, or which few lines you wrote yourself. What the capture prompt actually says. Whether you review what gets written or let it accumulate. What broke.

If you’re not doing it yet and this pushed you into trying, say so at the start and tell me what happened three weeks in. Including if the answer is that you did it twice and stopped, because that result is more useful than another enthusiastic write-up. The failure modes are what’s missing from every article I read while putting this together.

If enough of it turns out to be interesting, there’s probably a follow-up in it, built mostly out of what readers send rather than what I think. Credited unless you’d rather not be. A comment, an email, a reply on LinkedIn, whatever’s easiest.

The retrospective finally works. Let’s find out whether we actually run it.

TL;DR: Copying your project folders to a new laptop moves the files and leaves the work behind. Everything Claude Desktop actually remembers, your Cowork sessions, your MCP connector config, your Claude Code settings, lives in a Windows package sandbox that a normal search will never find. Zip that folder with the app closed and your history comes with you. Skip it and you start over with a very clean, very empty sidebar.

New Laptop Day

New laptop day is supposed to be a good day. Copy the projects, sign in, get back to work.

For most non-developers it generally is pretty straightforward, especially if your company manages backups and you use defaults. Sign in, wait for the sync icon to stop spinning, open the same three apps you always open. Whatever you’d customized was mostly customized inside something that follows your account, so it follows your account.

For developers and other power users it has never been that straightforward. There are a million little tweaks accumulated over years for personal preference and productivity, and not one of them is written down anywhere. The PATH entry you added at 11pm to make a build work. The tool installed from a zip file into a folder you invented. The config that lives three levels below AppData because that’s where the installer decided to put it. You don’t have a list. You have a vague sense that something will be missing, and you find out which something at the worst possible moment, usually about four days later.

Thanks to the popularity of Claude, now everyone gets those extra steps. And they’re not that straightforward even for the power users.

Here’s how it goes wrong. You copy the project folders. OneDrive handles the synced ones, a USB drive handles the local-only ones, file counts check out, you spot-check a few documents and nothing’s corrupted. Install Claude Desktop, sign in, open Cowork.

Empty.

The files are all there. The work is not. Every session, every bit of accumulated context, every conversation where you finally got Claude to understand your codebase, none of it came along. Because none of that lives in the project folder. It lives somewhere else entirely, and the app gives you no indication where.

Worth sorting out before you wipe the old machine, which is the point of no return most people hit about an hour after they think they’re done.

Two Kinds of Sessions, Only One of Which Is Your Problem

Some good news first. Cowork sessions now run remotely and are tied to your Claude account rather than your hardware. Sign into a new machine and those sessions are already there, waiting, automagically. Nothing to move, nothing to find. For once, the defaults crowd wins outright.

The catch is that this only holds for sessions created after remote sessions shipped. Anything older is a local artifact sitting on the old hard drive. If you’ve been using Cowork for a while, that’s likely most of your history.

So the question isn’t whether to migrate. It’s whether your sessions predate the cutover.

If none of them do, close the tab and enjoy the new laptop. Although before you go, it’s worth a moment’s honest reflection: if you’ve been at this for a while and have nothing accumulated that’s worth the trouble of moving, that’s telling you something. Not about the migration. About how much of Claude you’re actually using. A tool you’ve spent months teaching your projects, your standards, and your preferences to is a different tool than one you open to write emails. If none of this applies to you, the interesting question isn’t how to migrate. It’s what you’ve been leaving on the table.

For everyone else, keep reading.

Where It Actually Lives

Ask Claude where its own session data lives on Windows and it will tell you %APPDATA%\Claude\local-agent-mode-sessions\. It will tell you this confidently. Community migration tooling references the same path, so it isn’t inventing it from nothing.

It isn’t there.

Nor is it at %LOCALAPPDATA%\Claude\, which is the natural second guess and the next thing you’ll be told to try. You can run a recursive search across your entire user profile for audit.jsonl, the conversation log written inside every Cowork session, and get nothing back at all. That result is disorienting enough that you start to wonder whether the sessions ever existed on disk in the first place.

Whether that documented path was ever correct on Windows, or whether it’s a Mac convention that got generalized, isn’t something I can tell you. What matters is that on a current Windows install it’s a dead end, and it’s the dead end you’ll be pointed at first.

The real reason is architectural. Claude Desktop installs as a packaged Windows app, and packaged apps get their own private storage sandbox. Writes to the conventional locations get quietly redirected somewhere like this:

C:\Users\<username>\AppData\Local\Packages\Claude_<packageid>\LocalCache\Roaming\Claude\

Note the shape of that path. It ends in Roaming\Claude, exactly as documented. It’s just sitting under a package container that no reasonable person would think to check, which is why searching for the documented path fails while the documented path is, in a sense, still accurate.

The package ID is a short string of characters, and there’s no reason to guess at yours. Find it:

Get-ChildItem -Path $env:APPDATA, $env:LOCALAPPDATA, $env:USERPROFILE -Recurse -Filter "*claude*" -ErrorAction SilentlyContinue |
  Where-Object { $_.PSIsContainer } |
  Select-Object FullName |
  Out-File "$env:USERPROFILE\Desktop\claude-folders.txt"

That writes every Claude-related folder on the machine to your desktop. Open the file, look for the one containing local-agent-mode-sessions, and you have your real path. Two notes: run it in PowerShell, not Command Prompt, and expect it to take a minute or two while it walks the profile.

Depending on how and when Claude was installed, your data may genuinely sit in the plain %APPDATA%\Claude\ path. Both are possible. The one holding session subfolders with long UUID-style names is the one that matters. Don’t assume, check.

Claude Will Help You Move, and You Don’t Even Need to Buy It a Pizza Afterwards

Here’s the part that’s mildly funny in hindsight: the way to find all of this is to ask Claude, in Cowork, on the machine you’re migrating away from. It has shell access to the profile it’s running in. Point it at the problem and it will run the searches, read what comes back, and narrow the path down with you.

It will also send you to those two wrong folders on the way there, because the documented path and the actual path aren’t the same thing, and the documented path is what it reaches for first. That’s not a knock. It’s the ordinary pattern of working with these tools, and the fix is the same as always: make it show you the output rather than accept the summary. The searches above came out of exactly that back and forth. Claude proposed, the filesystem disagreed, and the third attempt found it.

Which is the useful lesson here, more than the folder path. The tool is genuinely good at the mechanical part, walking a filesystem, reading a directory listing, writing the PowerShell you’d otherwise be looking up. It is not reliable about where things live, because that’s a fact about your specific install and not something it can know from training. Use it for the legwork. Verify the destination yourself.

What to Copy and What to Leave

Open that Claude folder and you’ll find far more than sessions. Most of it is cache, crash logs, GPU state, and machine-specific scratch that regenerates on its own. Copying it doesn’t help and can actively cause conflicts.

Bring these:

• local-agent-mode-sessions is the whole reason you’re here. Your Cowork session history.
• claude_desktop_config.json holds your MCP server configuration. Lose it and every connector gets set up again from scratch. This is the one people don’t realize they needed until it’s gone.
• claude-code and claude-code-vm carry Claude Code settings and VM data, if you use it.
• vm_bundles for Claude Code VM bundles.
• ChromeNativeHost for the Claude in Chrome integration.
• config.json and cowork-enabled-cli-ops.json for general app and Cowork settings.
• git-worktrees.json if you run Claude Code against git worktrees.
• pending-uploads if anything is sitting in it.

Leave IndexedDB alone. It stores app state tied to your current signed-in session, and the new machine builds its own. Overwriting it invites problems you’ll spend an evening diagnosing.

Also grab C:\Users\<username>\.claude\ on the old machine. That’s a separate folder outside the sandbox, holding configuration and skills, and it goes to the same place on the new profile.

Zip It on the Old Machine

Rather than dragging ten items across a USB drive and hoping you got them all, package them once. Quit Claude Desktop completely first. Not the window, the app. Right-click the tray icon and choose Exit. Zipping live data files is how you end up with a corrupted history and no idea why.

Then, in PowerShell, substitute your own package ID into the first line and run this:

$Claude = "$env:LOCALAPPDATA\Packages\Claude_<packageid>\LocalCache\Roaming\Claude"

$Items = @(
  "local-agent-mode-sessions",
  "claude-code",
  "claude-code-vm",
  "vm_bundles",
  "ChromeNativeHost",
  "pending-uploads",
  "claude_desktop_config.json",
  "config.json",
  "cowork-enabled-cli-ops.json",
  "git-worktrees.json"
) | ForEach-Object { Join-Path $Claude $_ } | Where-Object { Test-Path $_ }

Compress-Archive -Path $Items -DestinationPath "$env:USERPROFILE\Desktop\claude-migration.zip" -CompressionLevel Optimal

The Where-Object { Test-Path $_ } line quietly skips anything you don’t have, so you can run it as-is whether or not you use Claude Code.

One detail that makes the other end easy: the archive stores paths relative to the items you named, not their full absolute paths. local-agent-mode-sessions\ and config.json land at the root of the zip. The archive is effectively a snapshot of the Claude folder itself, which means unpacking it is a single step with nothing to rearrange.

Then package the profile folder separately, since it lives elsewhere:

Compress-Archive -Path "$env:USERPROFILE\.claude" -DestinationPath "$env:USERPROFILE\Desktop\claude-dotfolder.zip"

Two zips on your desktop. Move them however you like: USB drive, OneDrive, network share.

If Compress-Archive throws a path-length error, that’s the 260-character Windows limit biting, and it’s plausible here given how deep the sandbox path already runs before your session UUIDs even start. Enable long paths in Windows, or fall back to robocopy with the /E switch to stage the folders somewhere shallow like C:\ClaudeMigration\ first, then zip from there.

Unzip It on the New Machine

1. Install Claude Desktop, sign in, and open Cowork once. This creates the directory structure you’re about to unpack into. Then quit completely again.
2. Find the package path on this machine. Run the same Get-ChildItem search from earlier. The package ID can differ between installs, so confirm rather than assume.
3. Unpack straight into the Claude folder. Because the archive is relative to that folder, everything lands where it belongs on its own:

$Target = "$env:LOCALAPPDATA\Packages\Claude_<packageid>\LocalCache\Roaming\Claude"

Expand-Archive -Path "$env:USERPROFILE\Desktop\claude-migration.zip" `
               -DestinationPath $Target -Force

-Force overwrites files that already exist and leaves everything else untouched. The only collisions are the config files the fresh install generated a minute ago, and replacing those with yours is the entire point.

4. Restore the profile folder:

Expand-Archive -Path "$env:USERPROFILE\Desktop\claude-dotfolder.zip" `
               -DestinationPath "$env:USERPROFILE" -Force

5. Restart Claude Desktop. Your old sessions should appear in the sidebar.
6. Reconnect your workspace folders. These are machine-specific paths and won’t follow you. Copy your project files first, then point Cowork at their new locations.
7. Reinstall plugins that rely on local MCP servers. Cloud-only plugins come across with your account.
8. Keep the old machine intact until you’ve verified all of it. Open a few migrated sessions, confirm your connectors work, and only then wipe.

The Same-Account Assumption

Everything above assumes one thing that’s easy to overlook: the Windows username is identical on both machines. When it is, every path inside those session files still resolves and the unpack just works.

When it isn’t, you have a problem the zip won’t solve. Sessions store absolute local paths, so C:\Users\OldName\Documents\... follows you onto a machine where no such user exists. The files arrive fine. The references inside them point at nothing.

If your usernames differ, this is the one case that needs an extra stop. Unpack to a scratch folder instead of straight into the target, run a find-and-replace across the JSON and JSONL files inside the extracted sessions to swap the old profile path for the new one, verify a single session opens correctly, and only then copy the corrected folders into place. Apply the same scrutiny if anything else moved, a different drive letter, a relocated Documents folder, OneDrive redirection that was on before and off now. Any of those breaks the same assumption in the same way.

Setting expectations honestly here: migrated sessions may land as readable history rather than fully resumable conversations. You get the record of what was discussed and decided, which is the part that took months to accumulate. Whether Cowork lets you pick up where you left off is a separate question, and one worth testing with a single session before you count on it for all of them.

With AI, Every How-To Has an Unknown Expiration Date

Everything above is a workaround for a design that’s already being replaced. That much is normal. What’s different now is that nobody can tell you when the replacement lands.

Software used to telegraph its changes. Version numbers, release notes, deprecation warnings, a beta period where the community wrote up what moved. A how-to written against version 4 stayed true until version 5, and version 5 announced itself. You could read a three-year-old post, check the version in the header, and know within seconds whether it still applied.

AI tools don’t work that way. They ship continuously, the client updates itself, and the thing you’re actually interacting with changes underneath a version number that may not move at all. Storage locations migrate. Local features become account features. The answer that was correct on Tuesday is wrong on Thursday, and nothing announces it. There’s no header to check.

Which is exactly what’s happening to this article. With sessions running remotely and tied to your account, the machine stops being where the work lives and becomes just a window onto it. Sign in anywhere and your history, your projects, and your scheduled tasks are already present. No folder to find, no zip to move, no package sandbox to go spelunking in. For anyone starting fresh today, this is already unnecessary.

That’s the right direction, and worth saying plainly rather than grumbling about the transition. Local-first storage bought you privacy and offline access at the cost of making your work a hostage to one piece of hardware. Account-first storage trades that the other way. Reasonable people weigh those differently, but nobody has ever been glad their context was trapped on a laptop with a failing battery.

The catch is the seam, and seams are always where the work is. Tools in transition leave a cohort stranded on the old model, holding data in a format the new model doesn’t automatically reach for. That cohort is anyone who adopted early, which is to say the people with the most accumulated context and the most to lose. Migration guides exist for the gap between what a tool used to be and what it’s becoming.

So treat this one, and every AI how-to you find, as perishable goods with no date stamped on the carton. Verify the path before you trust the instructions. If the folder isn’t where the article says it is, the article is probably older than the software. That will be true of this post eventually, and I can’t tell you when. Neither can anyone else. Until then, somebody has to move the boxes.

What This Actually Costs You

A little perspective on why any of us write these things down.

My first how-to post, back in 2002, was about building web services with Apache Axis. Working it out took the better part of two days: documentation that assumed you already knew the answer, examples that didn’t compile, and a long stretch of staring at a stack trace. The post that came out of it took a reader about twenty minutes. Two days of my confusion, compressed into twenty minutes of somebody else’s afternoon.

This one took about an hour of prompting and probing with Claude. It should take you fifteen minutes. Ten, if you run this post through an AI and ask it to strip out all my digressions, which I’d encourage, though I’d like it noted that the digressions are the part I enjoy.

The ratio held. It’s just faster on both ends now.

Fifteen minutes, then, against rebuilding context that took months to accumulate. That’s the entire calculation, and it’s the same calculation behind every unglamorous piece of groundwork in this business. Nobody gets excited about verifying a folder path. Everybody gets excited about the new laptop. The gap between those two feelings is where work disappears.

The broader lesson has nothing to do with Claude. Any tool you’ve spent real time training to your context is holding state somewhere, and “somewhere” is rarely where the marketing implies. Before you decommission a machine, ask what the tools on it know that the files don’t. Then go find out where they keep it.

Then wipe the old laptop. Not before.