diff --git a/packages/provider-core/src/server/maintenanceResolver.test.ts b/packages/provider-core/src/server/maintenanceResolver.test.ts
index cc20da24a33ec..fad5e5b80a40a 100644
--- a/packages/provider-core/src/server/maintenanceResolver.test.ts
+++ b/packages/provider-core/src/server/maintenanceResolver.test.ts
@@ -1084,10 +1084,10 @@ it.layer(
     }),
   );
 
-  it.effect.each(["wrapper", "symlink"])(
+  it.effect.each(["wrapper", "symlink", "Homebrew keg"])(
     "keeps a mise-owned %s in a native install location manual-only",
     (launcher, { skip }) => {
-      if (windowsHost || (launcher === "symlink" && !symlinksSupported)) skip();
+      if (windowsHost || (launcher !== "wrapper" && !symlinksSupported)) skip();
       return Effect.gen(function* () {
         const tempDir = yield* makeTempDir("t3-native-mise");
         const nativePath = NodePath.join(tempDir, ".local", "bin", "native-package-tool");
@@ -1098,14 +1098,17 @@ it.layer(
             '#!/bin/sh\nexec mise x native-package-tool -- native-package-tool "$@"\n',
           );
         } else {
-          const target = NodePath.join(
-            tempDir,
-            "mise",
-            "installs",
-            "native-package-tool",
-            "1.0.0",
-            "native-package-tool",
-          );
+          const target =
+            launcher === "symlink"
+              ? NodePath.join(
+                  tempDir,
+                  "mise",
+                  "installs",
+                  "native-package-tool",
+                  "1.0.0",
+                  "native-package-tool",
+                )
+              : NodePath.join(tempDir, "Cellar", "mise", "2026.9.1", "bin", "mise");
           writeExecutable(target);
           NodeFS.mkdirSync(NodePath.dirname(nativePath), { recursive: true });
           NodeFS.symlinkSync(target, nativePath);
@@ -1359,6 +1362,52 @@ it.layer(
       }),
   );
 
+  it.effect.each([
+    {
+      kind: "cask",
+      segments: ["Caskroom", "native-package-tool", "2.1.287", "native-package-tool"],
+      command: "brew upgrade --cask native-package-tool",
+    },
+    {
+      kind: "formula",
+      segments: ["Cellar", "native-package-tool", "2.1.287", "bin", "native-package-tool"],
+      command: "brew upgrade native-package-tool",
+    },
+  ])(
+    "upgrades a Homebrew $kind behind a native-looking launcher with brew",
+    (fixture) =>
+      Effect.gen(function* () {
+        const tempDir = yield* makeTempDir("t3-homebrew-native-launcher");
+        const brewPrefix = NodePath.join(tempDir, "opt", "homebrew");
+        writeExecutable(NodePath.join(brewPrefix, "bin", "brew"));
+        const target = NodePath.join(brewPrefix, ...fixture.segments);
+        writeExecutable(target);
+        const nativeBinDir = NodePath.join(tempDir, "home", ".local", "bin");
+        NodeFS.mkdirSync(nativeBinDir, { recursive: true });
+        NodeFS.symlinkSync(target, NodePath.join(nativeBinDir, "native-package-tool"));
+
+        const capabilities = yield* resolveProviderMaintenanceCapabilitiesEffect(
+          nativePackageToolUpdate,
+          {
+            binaryPath: "native-package-tool",
+            env: { PATH: [nativeBinDir, NodePath.join(brewPrefix, "bin")].join(":") },
+          },
+        ).pipe(
+          Effect.provideService(HostProcess.Platform, "darwin"),
+          Effect.provideService(
+            ChildProcessSpawner.ChildProcessSpawner,
+            stdoutSpawner((_, args) => (args[0] === "--prefix" ? `${brewPrefix}\n` : "")),
+          ),
+        );
+
+        expect(capabilities.update).toMatchObject({
+          command: fixture.command,
+          lockKey: "homebrew",
+        });
+      }),
+    { skip: !symlinksSupported || windowsHost },
+  );
+
   it("reads the stable formula version from brew info", () => {
     const info = JSON.stringify({ formulae: [{ versions: { stable: "2.1.5" } }] });
     const formula = { kind: "formula", name: "claude-code", prefix: "/opt/homebrew" } as const;
diff --git a/packages/provider-core/src/server/maintenanceResolver.ts b/packages/provider-core/src/server/maintenanceResolver.ts
index 7b1a46e1dbe47..112baf10db2b7 100644
--- a/packages/provider-core/src/server/maintenanceResolver.ts
+++ b/packages/provider-core/src/server/maintenanceResolver.ts
@@ -521,10 +521,12 @@ export const resolvePackageManagedProviderMaintenance = Effect.fn(
           : {}),
       })
     : manual;
-  // A native-looking launcher can still delegate to a mise-owned install.
+  const homebrew = homebrewOwnershipFromCommandPath(context.realCommandPath);
+  // A native-looking launcher can still delegate to a mise- or Homebrew-owned install.
   if (
     nativeUpdate?.isCommandPath &&
     commandPaths.some(nativeUpdate.isCommandPath) &&
+    !homebrew &&
     !commandPaths.some(isMiseCommandPath) &&
     !(yield* isMiseWrapperScript(context))
   ) {
@@ -614,7 +616,6 @@ export const resolvePackageManagedProviderMaintenance = Effect.fn(
     });
   }
 
-  const homebrew = homebrewOwnershipFromCommandPath(context.realCommandPath);
   if (
     commandPaths.some(isMiseCommandPath) ||
     // Mise shims resolve to the version manager's keg, not the provider's.