diff --git a/src/native/NativeMacOSProvider.ts b/src/native/NativeMacOSProvider.ts
index f4d06ae84..4fb002a92 100644
--- a/src/native/NativeMacOSProvider.ts
+++ b/src/native/NativeMacOSProvider.ts
@@ -7,7 +7,7 @@ import { inspectAppleDispatchMetadata } from "./AppleDispatchMetadata.js";
 import { observeNativeUi } from "./NativeUiObservation.js";
 import { LldbCallTracer, type NativeCallTracer } from "./LldbCallTracer.js";
 import { observeNativeCalls } from "./NativeCallObservation.js";
-import { dirname, isAbsolute, resolve } from "node:path";
+import { basename, dirname, isAbsolute, resolve } from "node:path";
 import { open, realpath, stat } from "node:fs/promises";
 
 import { z } from "zod";
@@ -1094,7 +1094,7 @@ const unreadablePlist = (
 ): AnalysisError => {
   const sentence = reason.endsWith(".") ? reason : `${reason}.`;
   // Name the default that is missing and the selection that still works.
-  const missingDefault = `The target has no readable Contents/Info.plist at ${path}: ${sentence} Select another plist in the target with the path input (CLI: --relative-path).`;
+  const missingDefault = `The target has no readable default plist at ${path}: ${sentence} Select another plist in the target with the path input (CLI: --relative-path).`;
   return requested === undefined
     ? new AnalysisCapabilityUnavailableError(
         IDENTITY.id,
@@ -1150,6 +1150,15 @@ const requireRegularPlist = async (
   }
 };
 
+/** The bundle whose Contents/MacOS directory directly holds `path`. */
+const macOSBundleRoot = (path: string): string | undefined => {
+  const programs = dirname(path);
+  const contents = dirname(programs);
+  return basename(programs) === "MacOS" && basename(contents) === "Contents"
+    ? dirname(contents)
+    : undefined;
+};
+
 const resolvePlistPath = async (
   target: BinaryTarget,
   requested: string | undefined,
@@ -1159,8 +1168,13 @@ const resolvePlistPath = async (
     if (requested !== undefined && isAbsolute(requested))
       return ok(resolve(requested));
     const sourceMetadata = await stat(source);
-    const root = sourceMetadata.isDirectory() ? source : dirname(target.path);
+    const root = sourceMetadata.isDirectory()
+      ? source
+      : (macOSBundleRoot(target.path) ?? dirname(target.path));
     if (requested !== undefined) return ok(resolve(root, requested));
+    // A selected plist file is itself the plist to inspect.
+    if (target.kind === "artifact" && target.format === "plist")
+      return ok(target.path);
     // A bundle target records the Info.plist its program file was declared
     // in: Contents/Info.plist, or the root plist of an iOS-style bundle.
     return ok(target.bundleInfoPlist ?? resolve(root, "Contents/Info.plist"));
diff --git a/tests/boundary/cli/nativePlistCli.test.ts b/tests/boundary/cli/nativePlistCli.test.ts
index 50ed030f3..324d4e20c 100644
--- a/tests/boundary/cli/nativePlistCli.test.ts
+++ b/tests/boundary/cli/nativePlistCli.test.ts
@@ -12,13 +12,22 @@ import { cliTest } from "../../support/cli/cliFixture.js";
 describe.skipIf(process.platform !== "darwin")(
   "native plist CLI selection",
   () => {
+    // Targets are app-relative: the bundle, its program file, or a plist file.
     cliTest.for([
-      ["default", undefined, "default"],
-      ["alternate", "Contents/Alternate.plist", "alternate"],
-      ["missing", "Contents/Missing.plist", undefined],
+      ["default", "", undefined, "default"],
+      ["alternate", "", "Contents/Alternate.plist", "alternate"],
+      ["missing", "", "Contents/Missing.plist", undefined],
+      ["program default", "Contents/MacOS/App", undefined, "default"],
+      [
+        "program alternate",
+        "Contents/MacOS/App",
+        "Contents/Alternate.plist",
+        "alternate",
+      ],
+      ["plist file", "Contents/Alternate.plist", undefined, "alternate"],
     ] as const)(
       "honors the $0 plist selection",
-      async ([, selected, identifier], { cli }) => {
+      async ([, target, selected, identifier], { cli }) => {
         const directory = await createTestTempDirectory("rea-plist-cli-");
         const app = join(directory, "Example.app");
         const contents = join(app, "Contents");
@@ -39,7 +48,7 @@ describe.skipIf(process.platform !== "darwin")(
         const result = await cli.run({
           arguments: [
             "inspect-plist",
-            app,
+            join(app, target),
             ...(selected === undefined ? [] : ["--relative-path", selected]),
             "--json",
           ],
@@ -55,7 +64,11 @@ describe.skipIf(process.platform !== "darwin")(
           expect(result.exitCode).toBe(0);
           expect(result.json).toMatchObject({
             normalized_result: {
-              source_path: join(app, selected ?? "Contents/Info.plist"),
+              source_path: join(
+                app,
+                selected ??
+                  (target.endsWith(".plist") ? target : "Contents/Info.plist"),
+              ),
               value: { CFBundleIdentifier: identifier },
             },
           });
diff --git a/tests/boundary/cli/nativePlistSelectionFailureCli.test.ts b/tests/boundary/cli/nativePlistSelectionFailureCli.test.ts
index e14ca4cc3..640e12b63 100644
--- a/tests/boundary/cli/nativePlistSelectionFailureCli.test.ts
+++ b/tests/boundary/cli/nativePlistSelectionFailureCli.test.ts
@@ -122,7 +122,7 @@ describe.skipIf(process.platform !== "darwin")(
           details: {
             operation: "inspect_plist",
             reason: expect.stringContaining(
-              `no readable Contents/Info.plist at ${join(directory, "Contents/Info.plist")}: no file exists there.`,
+              `no readable default plist at ${join(directory, "Contents/Info.plist")}: no file exists there.`,
             ),
           },
         });