diff --git a/src/application/Doctor.systemHost.test.ts b/src/application/Doctor.systemHost.test.ts
index c26cf15bd..7a160eae7 100644
--- a/src/application/Doctor.systemHost.test.ts
+++ b/src/application/Doctor.systemHost.test.ts
@@ -1,5 +1,9 @@
+import { mkdir, writeFile } from "node:fs/promises";
+import { join } from "node:path";
+
 import { expect, it } from "vitest";
 
+import { createTestTempDirectory } from "../../tests/fixtures/temporaryDirectory.js";
 import { systemDoctorHost } from "./Doctor.js";
 
 it("threads the selected host and environment into system diagnostics", async () => {
@@ -41,3 +45,64 @@ it("threads the selected host and environment into system diagnostics", async ()
     calls.every(({ environment: observed }) => observed === environment),
   ).toBe(true);
 });
+
+it.each([
+  [{ default: { appdir: "/Applications" } }, "/Applications"],
+  [
+    {
+      default: { appdir: "/Applications" },
+      env: { appdir: "/Env Apps" },
+      explicit: { appdir: "~/Tools" },
+    },
+    "HOME/Tools",
+  ],
+  [
+    { default: { appdir: "/Applications" }, env: { appdir: "/Env Apps" } },
+    "/Env Apps",
+  ],
+])(
+  "locates the Hopper cask from its Caskroom receipt without a cask command (%j)",
+  async (config, expectedAppdir) => {
+    const root = await createTestTempDirectory("rea-doctor-caskroom-");
+    const caskroom = join(root, "Caskroom");
+    const metadata = join(caskroom, "hopper-disassembler", ".metadata");
+    await mkdir(metadata, { recursive: true });
+    await writeFile(join(metadata, "config.json"), JSON.stringify(config));
+    const calls: (readonly string[])[] = [];
+    const host = systemDoctorHost({
+      platform: "darwin",
+      environment: { HOME: join(root, "home") },
+      execFileOutput: async (_command, arguments_) => {
+        calls.push(arguments_);
+        return { stdout: `${caskroom}\n`, stderr: "" };
+      },
+    });
+
+    expect(await host.brewHopperPath()).toBe(
+      join(
+        expectedAppdir.replace("HOME", join(root, "home")),
+        "Hopper Disassembler.app/Contents/MacOS/hopper",
+      ),
+    );
+    // A cask argument makes Homebrew fetch and cache its API data.
+    expect(calls).toEqual([["--caskroom"]]);
+  },
+);
+
+it("reports no Homebrew Hopper when the cask has no receipt", async () => {
+  const caskroom = await createTestTempDirectory("rea-doctor-caskroom-");
+  const calls: (readonly string[])[] = [];
+  const host = systemDoctorHost({
+    platform: "darwin",
+    environment: { HOME: caskroom },
+    execFileOutput: async (_command, arguments_) => {
+      calls.push(arguments_);
+      return { stdout: `${caskroom}\n`, stderr: "" };
+    },
+  });
+
+  expect(await host.brewHopperPath()).toBeUndefined();
+  expect(
+    calls.every((arguments_) => arguments_.join(" ") === "--caskroom"),
+  ).toBe(true);
+});
diff --git a/src/application/Doctor.ts b/src/application/Doctor.ts
index 9ff752f3a..7b523b428 100644
--- a/src/application/Doctor.ts
+++ b/src/application/Doctor.ts
@@ -7,7 +7,7 @@ import { analysisErrorRemediationAction } from "../domain/analysisErrorPresentat
 import { parseBinaryTarget } from "./BinaryTargetResolver.js";
 import { execFileOutput } from "../process/ExecFileOutput.js";
 import type { JsonValue } from "../domain/jsonValue.js";
-import { probeHomebrew } from "./homebrew.js";
+import { installedCaskAppdir, probeHomebrew } from "./homebrew.js";
 import {
   linuxHopperBinarySupported,
   linuxSharedLibrariesAvailable,
@@ -380,20 +380,30 @@ export const systemDoctorHost = (
     supportedLinuxHopper: linuxHopperBinarySupported,
     async brewHopperPath() {
       return probeHomebrew(async (command) => {
+        let caskroom: string;
         try {
-          const prefix = (
+          // Without a cask argument, `--caskroom` does not load Homebrew's
+          // cask API, so doctor writes no Homebrew cache files.
+          caskroom = (
             await hostExecFileOutput(
               command,
-              ["--prefix", "--cask", "hopper-disassembler"],
+              ["--caskroom"],
               commandEnvironment,
             )
           ).stdout.trim();
-          return `${prefix}/Hopper Disassembler.app/Contents/MacOS/hopper`;
         } catch (cause: unknown) {
           // best-effort cleanup: optional Homebrew probing; absence means uninstalled.
           void cause;
           return undefined;
         }
+        const appdir = await installedCaskAppdir(
+          caskroom,
+          "hopper-disassembler",
+          homeDirectory,
+        );
+        return appdir === undefined
+          ? undefined
+          : join(appdir, "Hopper Disassembler.app/Contents/MacOS/hopper");
       });
     },
     manualHopperPaths: () => manualHopperPaths(homeDirectory),
diff --git a/src/application/homebrew.ts b/src/application/homebrew.ts
index 2b2070001..ae8710839 100644
--- a/src/application/homebrew.ts
+++ b/src/application/homebrew.ts
@@ -1,3 +1,8 @@
+import { readFile } from "node:fs/promises";
+import { join } from "node:path";
+
+import { z } from "zod";
+
 /** Standard executable names and locations used to discover Homebrew. */
 const HOMEBREW_COMMANDS = [
   "brew",
@@ -19,3 +24,54 @@ export const probeHomebrew = async <T>(
   }
   return undefined;
 };
+
+const caskDirectoriesSchema = z
+  .object({ appdir: z.string().min(1).optional() })
+  .loose();
+const caskConfigSchema = z
+  .object({
+    default: caskDirectoriesSchema.optional(),
+    env: caskDirectoriesSchema.optional(),
+    explicit: caskDirectoriesSchema.optional(),
+  })
+  .loose();
+
+/**
+ * Read the application directory Homebrew recorded when it installed a cask,
+ * in Homebrew's precedence: explicit option, then environment, then default.
+ * Reading the Caskroom avoids `brew` cask commands, which refresh Homebrew's
+ * API and bootsnap caches.
+ */
+export const installedCaskAppdir = async (
+  caskroom: string,
+  token: string,
+  home: string,
+): Promise<string | undefined> => {
+  let text: string;
+  try {
+    text = await readFile(
+      join(caskroom, token, ".metadata", "config.json"),
+      "utf8",
+    );
+  } catch (cause: unknown) {
+    // An absent or unreadable receipt means the cask is not installed here.
+    void cause;
+    return undefined;
+  }
+  let parsed: unknown;
+  try {
+    parsed = JSON.parse(text);
+  } catch (cause: unknown) {
+    // A malformed receipt does not identify an application directory.
+    void cause;
+    return undefined;
+  }
+  const config = caskConfigSchema.safeParse(parsed);
+  if (!config.success) return undefined;
+  const appdir =
+    config.data.explicit?.appdir ??
+    config.data.env?.appdir ??
+    config.data.default?.appdir;
+  if (appdir === undefined) return undefined;
+  return appdir.startsWith("~/") ? join(home, appdir.slice(2)) : appdir;
+};