diff --git a/tests/boundary/filesystem/ciCachePolicy.test.ts b/tests/boundary/filesystem/ciCachePolicy.test.ts
index 058c47c94b..d13ef20b2b 100644
--- a/tests/boundary/filesystem/ciCachePolicy.test.ts
+++ b/tests/boundary/filesystem/ciCachePolicy.test.ts
@@ -10,6 +10,7 @@ import {
   writeFile,
 } from "node:fs/promises";
 import { delimiter, join } from "node:path";
+import { runInNewContext } from "node:vm";
 
 import { describe, expect, it } from "vitest";
 import { parse } from "yaml";
@@ -17,6 +18,69 @@ import { z } from "zod";
 
 import { createTestTempDirectory } from "../../fixtures/temporaryDirectory.js";
 
+// These policy expressions use only JS-compatible boolean operators, property
+// access, literals and format; exercise the parsed workflow rather than copies.
+const evaluatePolicy = (
+  expression: string,
+  context: Record<string, unknown>,
+): unknown =>
+  runInNewContext(
+    expression.replace(/^\$\{\{\s*|\s*\}\}$/gu, ""),
+    {
+      ...context,
+      format: (template: string, value: string) =>
+        template.replace("{0}", value),
+    },
+    { timeout: 100 },
+  );
+
+const assertRetentionPolicy = (expression: string): void => {
+  for (const conclusion of [
+    "success",
+    "failure",
+    "timed_out",
+    "cancelled",
+    "skipped",
+    "action_required",
+  ]) {
+    for (const event of [
+      "push",
+      "schedule",
+      "workflow_dispatch",
+      "pull_request",
+    ]) {
+      for (const [repositoryName, branch] of [
+        ["owner/repo", "main"],
+        ["untrusted/fork", "main"],
+        ["owner/repo", "feature"],
+      ]) {
+        const permitted =
+          repositoryName === "owner/repo" &&
+          branch === "main" &&
+          event !== "pull_request" &&
+          ["success", "failure", "timed_out", "cancelled"].includes(conclusion);
+        expect(
+          evaluatePolicy(expression, {
+            github: {
+              repository: "owner/repo",
+              event: {
+                repository: { default_branch: "main" },
+                workflow_run: {
+                  conclusion,
+                  event,
+                  head_repository: { full_name: repositoryName },
+                  head_branch: branch,
+                },
+              },
+            },
+          }),
+          `${repositoryName}:${branch}:${event}:${conclusion}`,
+        ).toBe(permitted);
+      }
+    }
+  }
+};
+
 const repository = process.cwd();
 const actionPath = join(repository, ".github/actions/npm-cache/action.yml");
 const readAction = async () =>
@@ -512,30 +576,7 @@ it("deletes superseded caches only from the trusted follow-up workflow", async (
     actions: "write",
   });
   const job = workflow.jobs.retain;
-  expect(job?.if).toContain(
-    "github.event.workflow_run.conclusion == 'success'",
-  );
-  expect(job?.if).toContain(
-    "github.event.workflow_run.conclusion == 'failure'",
-  );
-  expect(job?.if).toContain(
-    "github.event.workflow_run.conclusion == 'timed_out'",
-  );
-  expect(job?.if).toContain(
-    "github.event.workflow_run.conclusion == 'cancelled'",
-  );
-  expect(job?.if).toContain(
-    "github.event.workflow_run.head_repository.full_name == github.repository",
-  );
-  expect(job?.if).toContain(
-    "github.event.workflow_run.head_branch == github.event.repository.default_branch",
-  );
-  expect(job?.if).toContain("github.event.workflow_run.event == 'push'");
-  expect(job?.if).toContain("github.event.workflow_run.event == 'schedule'");
-  expect(job?.if).toContain(
-    "github.event.workflow_run.event == 'workflow_dispatch'",
-  );
-  expect(job?.if).not.toContain("pull_request");
+  assertRetentionPolicy(z.string().parse(job?.if));
   const steps = job?.steps ?? [];
   expect(steps.some((step) => step.run === "npm ci")).toBe(false);
   const checkouts = steps.filter(
@@ -729,6 +770,43 @@ it("exports turbo remote-cache credentials wherever a workflow runs turbo", asyn
         expect(cache, `${file}:${name}`).not.toContain("local:rw,remote:r'");
       } else expect(cache, `${file}:${name}`).toContain("local:rw,remote:r'");
       expect(cache, `${file}:${name}`).toContain("local:rw,remote:rw");
+      for (const event of [
+        "push",
+        "schedule",
+        "workflow_dispatch",
+        "pull_request",
+        "workflow_call",
+      ]) {
+        for (const ref of ["refs/heads/main", "refs/heads/feature"]) {
+          for (const grant of [false, true]) {
+            const permitted =
+              (grantsReleaseWrite && grant) ||
+              (ref === "refs/heads/main" &&
+                (["push", "schedule", "workflow_dispatch"].includes(event) ||
+                  (grantsCalledEvent && event === "workflow_call")));
+            const context = {
+              github: {
+                ref,
+                event_name: event,
+                event: { repository: { default_branch: "main" } },
+              },
+              inputs: { remote_cache_write: grant },
+              secrets: { TURBO_TOKEN: "recording-token" },
+            };
+            const label = `${file}:${name}:${event}:${ref}:${grant}`;
+            expect(evaluatePolicy(token, context), label).toBe(
+              permitted ? "recording-token" : "",
+            );
+            expect(evaluatePolicy(cache, context), label).toBe(
+              permitted
+                ? "local:rw,remote:rw"
+                : grantsReleaseWrite
+                  ? "local:rw"
+                  : "local:rw,remote:r",
+            );
+          }
+        }
+      }
       expect(env.TURBO_TEAM, `${file}:${name}`).toBe("${{ vars.TURBO_TEAM }}");
     }
   }
diff --git a/tests/boundary/filesystem/ciChangeScope.test.ts b/tests/boundary/filesystem/ciChangeScope.test.ts
index c3b560ec47..a0a07cffd5 100644
--- a/tests/boundary/filesystem/ciChangeScope.test.ts
+++ b/tests/boundary/filesystem/ciChangeScope.test.ts
@@ -501,6 +501,7 @@ it("selects only a trusted successful ancestor from recent CI push runs", async
 }) => {
   skip(process.platform === "win32", "the fake gh is a POSIX shell script");
   const { directory, base } = await fixture();
+  const foreignBase = await change(directory, ["README.md"]);
   const head = await change(directory, ["src/evm/client.ts"]);
   const bin = join(directory, "fake-bin");
   await mkdir(bin);
@@ -517,7 +518,7 @@ it("selects only a trusted successful ancestor from recent CI push runs", async
           conclusion: "success",
           head_branch: "main",
           head_repository: { full_name: "untrusted/fork" },
-          head_sha: base,
+          head_sha: foreignBase,
         },
         {
           event: "push",