leesangb · leesangb · Jul 18, 2026 · Jul 18, 2026
diff --git a/.changeset/sync-herdr-plugin-on-update.md b/.changeset/sync-herdr-plugin-on-update.md
@@ -0,0 +1,5 @@
+---
+"@leesangb/wt": minor
+---
+
+Keep an installed wt Herdr plugin in sync with the wt release selected by `wt update`.
diff --git a/README.md b/README.md
@@ -349,6 +349,11 @@ Skip removing quarantine attribute for standalone binary installs:
 wt update --no-remove-quarantine
 ```
 
+If the `wt.herdr` plugin was installed from `leesangb/wt`, `wt update` also
+syncs it to the same release tag. Locally linked plugins and plugins from other
+repositories are left unchanged. Use `wt update --force` to reinstall an
+already matching plugin version.
+
 ### List all worktrees
 
 ```bash

diff --git a/src/app/use-cases/update-installation.test.ts b/src/app/use-cases/update-installation.test.ts
@@ -18,6 +18,8 @@ describe("update installation use case", () => {
     const delegatedCommands: string[] = [];
     const executedPlans: Array<{ args: string[]; displayCommand: string }> = [];
     const refreshedBinaries: string[] = [];
+    const versionedBinaries: string[] = [];
+    const syncedVersions: string[] = [];
 
     const result = await updateInstallation("0.3.0", {}, {
       processInfo: {
@@ -26,13 +28,21 @@ describe("update installation use case", () => {
       },
       onBeforeHomebrewUpdate: (command) => delegatedCommands.push(command),
       runHomebrewUpdate: (plan) => executedPlans.push(plan),
+      readInstalledVersion: (binaryPath) => {
+        versionedBinaries.push(binaryPath);
+        return "0.4.0";
+      },
       refreshShellWrappers: (binaryPath) => {
         refreshedBinaries.push(binaryPath);
         return {
           refreshedShells: ["zsh"],
           warnings: [],
         };
       },
+      syncHerdrPlugin: async (version) => {
+        syncedVersions.push(version);
+        return { status: "updated", version };
+      },
     });
 
     expect(result).toEqual({
@@ -42,6 +52,7 @@ describe("update installation use case", () => {
         refreshedShells: ["zsh"],
         warnings: [],
       },
+      herdrPlugin: { status: "updated", version: "0.4.0" },
     });
     expect(delegatedCommands).toEqual(["brew upgrade wt"]);
     expect(executedPlans).toEqual([
@@ -51,13 +62,16 @@ describe("update installation use case", () => {
       },
     ]);
     expect(refreshedBinaries).toEqual(["/opt/homebrew/bin/wt"]);
+    expect(versionedBinaries).toEqual(["/opt/homebrew/bin/wt"]);
+    expect(syncedVersions).toEqual(["0.4.0"]);
   });
 
   test("refreshes existing shell wrappers after a standalone binary update", async () => {
     const downloads: string[] = [];
     const replacements: Array<{ tempPath: string; execPath: string }> = [];
     const quarantines: string[] = [];
     const refreshedBinaries: string[] = [];
+    const syncedHerdrPlugins: Array<{ version: string; force: boolean }> = [];
 
     const result = await updateInstallation(
       "0.6.0",
@@ -86,6 +100,10 @@ describe("update installation use case", () => {
             warnings: [],
           };
         },
+        syncHerdrPlugin: async (version, { force }) => {
+          syncedHerdrPlugins.push({ version, force });
+          return { status: "updated", version };
+        },
       }
     );
 
@@ -100,6 +118,7 @@ describe("update installation use case", () => {
     ]);
     expect(quarantines).toEqual(["/Users/test/.local/bin/wt"]);
     expect(refreshedBinaries).toEqual(["/Users/test/.local/bin/wt"]);
+    expect(syncedHerdrPlugins).toEqual([{ version: "0.6.1", force: false }]);
     expect(result).toEqual({
       strategy: "standalone",
       currentVersion: "0.6.0",
@@ -110,6 +129,38 @@ describe("update installation use case", () => {
         refreshedShells: ["bash", "zsh"],
         warnings: [],
       },
+      herdrPlugin: {
+        status: "updated",
+        version: "0.6.1",
+      },
+    });
+  });
+
+  test("syncs the Herdr plugin when the standalone binary is already current", async () => {
+    const syncedVersions: string[] = [];
+
+    const result = await updateInstallation(
+      "0.6.1",
+      { version: "0.6.1" },
+      {
+        arch: "arm64",
+        platform: "darwin",
+        processInfo: {
+          argv0: "wt",
+          execPath: "/Users/test/.local/bin/wt",
+        },
+        syncHerdrPlugin: async (version) => {
+          syncedVersions.push(version);
+          return { status: "up-to-date", version };
+        },
+      }
+    );
+
+    expect(syncedVersions).toEqual(["0.6.1"]);
+    expect(result).toMatchObject({
+      strategy: "standalone",
+      updated: false,
+      herdrPlugin: { status: "up-to-date", version: "0.6.1" },
     });
   });
 });
diff --git a/src/app/use-cases/update-installation.ts b/src/app/use-cases/update-installation.ts
@@ -23,6 +23,11 @@ import {
   type HomebrewUpdatePlan,
 } from "../../infra/update/homebrew.js";
 import { compareVersions } from "../../infra/update/version.js";
+import {
+  syncInstalledWtHerdrPlugin,
+  type HerdrPluginSyncResult,
+} from "../../infra/herdr/client.js";
+import { readInstalledWtVersion } from "../../infra/update/installed-version.js";
 
 const BINARY_NAME = "wt";
 const RUNTIME_LAUNCHERS = new Set(["bun", "node"]);
@@ -40,12 +45,14 @@ export interface StandaloneUpdateInstallationResult {
   updated: boolean;
   assetName?: string;
   shellIntegration?: RefreshShellWrappersResult;
+  herdrPlugin?: HerdrPluginSyncResult;
 }
 
 export interface HomebrewDelegatedUpdateResult {
   strategy: "homebrew";
   delegatedCommand: string;
   shellIntegration: RefreshShellWrappersResult;
+  herdrPlugin?: HerdrPluginSyncResult;
 }
 
 export type UpdateInstallationResult =
@@ -61,9 +68,14 @@ export interface UpdateInstallationContext {
   downloadBinary?: (url: string) => Promise<string>;
   onBeforeHomebrewUpdate?: (command: string) => void;
   refreshShellWrappers?: (binaryPath: string) => RefreshShellWrappersResult;
+  readInstalledVersion?: (binaryPath: string) => string;
   removeMacosQuarantine?: (execPath: string) => Promise<void>;
   replaceCurrentBinary?: (tempPath: string, execPath: string) => void;
   runHomebrewUpdate?: (plan: HomebrewUpdatePlan) => void;
+  syncHerdrPlugin?: (
+    version: string,
+    options: { force: boolean }
+  ) => Promise<HerdrPluginSyncResult>;
 }
 
 function assertVersionFormat(version: string, label: string): void {
@@ -132,6 +144,24 @@ function refreshShellWrappers(
   )(binaryPath);
 }
 
+async function syncHerdrPlugin(
+  version: string,
+  options: UpdateInstallationOptions,
+  context: UpdateInstallationContext
+): Promise<HerdrPluginSyncResult | undefined> {
+  try {
+    return await (context.syncHerdrPlugin ?? syncInstalledWtHerdrPlugin)(
+      version,
+      { force: options.force === true }
+    );
+  } catch (error) {
+    return {
+      status: "failed",
+      warning: error instanceof Error ? error.message : String(error),
+    };
+  }
+}
+
 async function updateStandaloneInstallation(
   currentVersion: string,
   options: UpdateInstallationOptions,
@@ -174,12 +204,18 @@ async function updateStandaloneInstallation(
     assertVersionFormat(targetVersion, "release");
 
     if (compareVersions(targetVersion, currentVersion) <= 0 && !options.force) {
+      const herdrPlugin = await syncHerdrPlugin(
+        currentVersion,
+        options,
+        context
+      );
       return {
         strategy: "standalone",
         currentVersion,
         targetVersion,
         updated: false,
         assetName,
+        ...(herdrPlugin ? { herdrPlugin } : {}),
       };
     }
 
@@ -196,12 +232,18 @@ async function updateStandaloneInstallation(
     assertVersionFormat(targetVersion, "requested");
 
     if (compareVersions(targetVersion, currentVersion) <= 0 && !options.force) {
+      const herdrPlugin = await syncHerdrPlugin(
+        currentVersion,
+        options,
+        context
+      );
       return {
         strategy: "standalone",
         currentVersion,
         targetVersion,
         updated: false,
         assetName,
+        ...(herdrPlugin ? { herdrPlugin } : {}),
       };
     }
 
@@ -223,6 +265,7 @@ async function updateStandaloneInstallation(
   }
 
   const shellIntegration = refreshShellWrappers(binaryPath, context);
+  const herdrPlugin = await syncHerdrPlugin(targetVersion, options, context);
 
   return {
     strategy: "standalone",
@@ -231,6 +274,7 @@ async function updateStandaloneInstallation(
     updated: true,
     assetName,
     shellIntegration,
+    ...(herdrPlugin ? { herdrPlugin } : {}),
   };
 }
 
@@ -246,15 +290,29 @@ export async function updateInstallation(
 
     context.onBeforeHomebrewUpdate?.(plan.displayCommand);
     (context.runHomebrewUpdate ?? runHomebrewUpdate)(plan);
-    const shellIntegration = refreshShellWrappers(
-      resolveHomebrewShellBinaryPath(context.processInfo),
-      context
-    );
+    const binaryPath = resolveHomebrewShellBinaryPath(context.processInfo);
+    const shellIntegration = refreshShellWrappers(binaryPath, context);
+    let installedVersion: string | undefined;
+    let herdrPlugin: HerdrPluginSyncResult | undefined;
+
+    try {
+      installedVersion = (
+        context.readInstalledVersion ?? readInstalledWtVersion
+      )(binaryPath);
+      assertVersionFormat(installedVersion, "installed");
+      herdrPlugin = await syncHerdrPlugin(installedVersion, options, context);
+    } catch (error) {
+      herdrPlugin = {
+        status: "failed",
+        warning: `Could not sync the wt Herdr plugin: ${error instanceof Error ? error.message : String(error)}`,
+      };
+    }
 
     return {
       strategy: "homebrew",
       delegatedCommand: plan.displayCommand,
       shellIntegration,
+      ...(herdrPlugin ? { herdrPlugin } : {}),
     };
   }
 

diff --git a/src/commands/update.ts b/src/commands/update.ts
@@ -38,6 +38,32 @@ function printShellIntegrationRefresh(result: UpdateInstallationResult): void {
   }
 }
 
+function printHerdrPluginSync(result: UpdateInstallationResult): void {
+  const plugin = result.herdrPlugin;
+
+  if (!plugin) {
+    return;
+  }
+
+  if (plugin.status === "updated") {
+    console.log(
+      chalk.green(`✓ Updated wt Herdr plugin to version ${plugin.version}.`)
+    );
+    return;
+  }
+
+  if (plugin.status === "up-to-date") {
+    console.log(
+      chalk.dim(`wt Herdr plugin is up to date (${plugin.version}).`)
+    );
+    return;
+  }
+
+  if (plugin.warning) {
+    console.log(chalk.yellow(`Warning: ${plugin.warning}`));
+  }
+}
+
 export async function updateCommand(
   options: UpdateInstallationOptions
 ): Promise<void> {
@@ -55,6 +81,7 @@ export async function updateCommand(
         },
       });
       printShellIntegrationRefresh(result);
+      printHerdrPluginSync(result);
       return;
     }
 
@@ -82,11 +109,13 @@ export async function updateCommand(
         );
         console.log(chalk.dim("Use --force to re-download the current version."));
       }
+      printHerdrPluginSync(result);
       return;
     }
 
     console.log(chalk.green(`✓ Updated wt to version ${result.targetVersion}`));
     printShellIntegrationRefresh(result);
+    printHerdrPluginSync(result);
     console.log(chalk.dim("Run: wt --version to verify."));
   });
 }