diff --git a/src/domain/process/processScenario.ts b/src/domain/process/processScenario.ts
index a87ffd86e..e98d7a537 100644
--- a/src/domain/process/processScenario.ts
+++ b/src/domain/process/processScenario.ts
@@ -128,6 +128,9 @@ export const processComparisonContract = (
     : {}),
   limits: scenario.limits,
   normalization: scenario.normalization,
+  ...(scenario.normalization.paths
+    ? { path_normalization_version: "longest-original-paths-v1" }
+    : {}),
   ...(scenario.normalization.ports
     ? { port_normalization_version: "contextual-endpoints-v2" }
     : {}),
diff --git a/src/process/capture/ProcessNormalization.test.ts b/src/process/capture/ProcessNormalization.test.ts
index 9c9ba1951..e5ef61062 100644
--- a/src/process/capture/ProcessNormalization.test.ts
+++ b/src/process/capture/ProcessNormalization.test.ts
@@ -266,3 +266,47 @@ it("normalizes representative process identities and preserves null, zero, and u
     "<working-directory>/program child 42020 parent 41010 group 43030 session 44040 listen:<port> selected",
   );
 });
+
+it("normalizes nested paths once using the most specific selected identity", () => {
+  const declared = parseProcessScenario({
+    executable: "/workspace/project/bin/program",
+    working_directory: "/workspace/project",
+    filesystem_observation_paths: [
+      "/workspace/project/data",
+      "/workspace/project/data/cache",
+    ],
+    normalization: { paths: true, pids: false, ports: false, patterns: [] },
+  });
+  expect(
+    normalizeProcessText(
+      "/workspace/project/bin/program /workspace/project/data/cache/item /workspace/project/data/result /workspace/project/log /workspace/tmp",
+      declared,
+      "/workspace",
+      rootPid,
+    ),
+  ).toBe(
+    "<executable> <filesystem-root-1>/item <filesystem-root-0>/result <working-directory>/log <temporary-root>/tmp",
+  );
+});
+
+it("treats path metacharacters literally while preferring nested observed roots", () => {
+  const declared = parseProcessScenario({
+    executable: "/selected/[tool]+",
+    working_directory: "/selected",
+    filesystem_observation_paths: [
+      "/selected/(data)",
+      "/selected/(data)/cache",
+    ],
+    normalization: { paths: true, pids: false, ports: false, patterns: [] },
+  });
+  expect(
+    normalizeProcessText(
+      "/selected/[tool]+ /selected/(data)/cache/item /selected/(data)/file /selected/log /selected/toolll",
+      declared,
+      "/tmp",
+      rootPid,
+    ),
+  ).toBe(
+    "<executable> <filesystem-root-1>/item <filesystem-root-0>/file <working-directory>/log <working-directory>/toolll",
+  );
+});
diff --git a/src/process/capture/ProcessNormalization.ts b/src/process/capture/ProcessNormalization.ts
index 9364ec95b..74db31b1c 100644
--- a/src/process/capture/ProcessNormalization.ts
+++ b/src/process/capture/ProcessNormalization.ts
@@ -17,19 +17,8 @@ export const normalizeProcessText = (
   pid: number,
 ): string => {
   let normalized = value;
-  if (scenario.normalization.paths) {
-    normalized = normalized.replaceAll(temporaryRoot, "<temporary-root>");
-    normalized = normalized.replaceAll(
-      scenario.working_directory,
-      "<working-directory>",
-    );
-    normalized = normalized.replaceAll(scenario.executable, "<executable>");
-    for (const [index, root] of scenario.filesystem_observation_paths.entries())
-      normalized = normalized.replaceAll(
-        root,
-        `<filesystem-root-${String(index)}>`,
-      );
-  }
+  if (scenario.normalization.paths)
+    normalized = normalizePathTokens(normalized, scenario, temporaryRoot);
   if (scenario.normalization.ports)
     normalized = normalizePortTokens(normalized);
   if (scenario.normalization.pids)
@@ -44,6 +33,39 @@ export const normalizeProcessText = (
   return normalized;
 };
 
+/** Match original paths once, preferring the most specific selected identity. */
+const normalizePathTokens = (
+  value: string,
+  scenario: ProcessScenario,
+  temporaryRoot: string,
+): string => {
+  const aliases = new Map<string, string>();
+  const selected: readonly (readonly [string, string])[] = [
+    [temporaryRoot, "<temporary-root>"],
+    [scenario.working_directory, "<working-directory>"],
+    [scenario.executable, "<executable>"],
+    ...scenario.filesystem_observation_paths.map(
+      (root, index): readonly [string, string] => [
+        root,
+        `<filesystem-root-${String(index)}>`,
+      ],
+    ),
+  ];
+  for (const [path, alias] of selected)
+    if (path !== "" && !aliases.has(path)) aliases.set(path, alias);
+  const paths = [...aliases.keys()].sort(
+    (left, right) => right.length - left.length,
+  );
+  if (paths.length === 0) return value;
+  const pattern = paths
+    .map((path) => path.replace(/[.*+?^${}()|[\]\\]/gu, "\\$&"))
+    .join("|");
+  return value.replace(
+    new RegExp(pattern, "gu"),
+    (path) => aliases.get(path) ?? path,
+  );
+};
+
 // A port may end a sentence, but a period followed by a letter, digit, or
 // underscore in any script continues a decimal, version, or host name and is
 // not a port boundary.
diff --git a/tests/boundary/process/processCaptureNormalization.test.ts b/tests/boundary/process/processCaptureNormalization.test.ts
index 965dc2af5..2837ccf40 100644
--- a/tests/boundary/process/processCaptureNormalization.test.ts
+++ b/tests/boundary/process/processCaptureNormalization.test.ts
@@ -1,4 +1,4 @@
-import { readFile } from "node:fs/promises";
+import { mkdir, readFile, symlink } from "node:fs/promises";
 import { join } from "node:path";
 import { fileURLToPath } from "node:url";
 import { expect, it } from "vitest";
@@ -202,3 +202,61 @@ itWithLinuxCaptureCapability.each([false, true])(
   },
   20_000,
 );
+
+itWithCaptureCapability(
+  "preserves selected nested path identities in actual PTY Evidence",
+  async () => {
+    const root = await createTestTempDirectory("rea-process-nested-paths-");
+    const executable = join(root, "selected-node");
+    const observed = join(root, "data");
+    await symlink(process.execPath, executable);
+    await mkdir(observed);
+    const original = `${executable}\n${observed}/result\n${root}/log`;
+    const scenario = parseProcessScenario({
+      executable,
+      working_directory: root,
+      filesystem_observation_paths: [observed],
+      arguments: ["-e", `process.stdout.write(${JSON.stringify(original)})`],
+      normalization: { paths: true, pids: false, ports: false, patterns: [] },
+      settle_ms: 100,
+    });
+    const result = await captureProcessScenario(scenario);
+    if (!result.ok) throw result.error;
+    const capture = parseProcessCapture(
+      createProcessCaptureEvidence(scenario, result.value).normalized_result,
+    );
+    expect(capture.frames.map(({ data }) => data).join("")).toBe(
+      "<executable>\r\n<filesystem-root-0>/result\r\n<working-directory>/log",
+    );
+    expect(
+      capture.frames.map(({ raw_data, data }) => raw_data ?? data).join(""),
+    ).toBe(original.replaceAll("\n", "\r\n"));
+    expect(capture.manifest.comparison_contract).toHaveProperty(
+      "path_normalization_version",
+      "longest-original-paths-v1",
+    );
+    const legacyContract = { ...capture.manifest.comparison_contract };
+    delete legacyContract.path_normalization_version;
+    const legacy = parseProcessCapture({
+      ...capture,
+      manifest: {
+        ...capture.manifest,
+        comparison_contract: legacyContract,
+        comparison_contract_sha256: digestProcessCommitment(legacyContract),
+      },
+    });
+    expect(() => compareProcessCaptures(legacy, capture)).toThrow(
+      expect.objectContaining({
+        issues: [
+          expect.objectContaining({ expected: ["path_normalization_version"] }),
+        ],
+      }),
+    );
+    expect(capture.exit).toMatchObject({ code: 0, reason: "exited" });
+    expect(capture.cleanup).toMatchObject({
+      owned_process_group: "verified",
+      temporary_root: "removed",
+    });
+  },
+  20_000,
+);